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5-Day Middleburg Itinerary

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Wanderlog staff
Updated
• updatedAug 20, 2025

Middleburg in 5 days

If you only have 5 days to spend in Middleburg, we’ve narrowed down the top places you should check out to get the best experience of your time here.
With favorites like Middleburg Deli, King Street Oyster Bar Middleburg, and Cana Vineyards and Winery of Middleburg, we’ll make sure you don’t miss out on all the must sees. We even included some of our favorite food spots around the area, like The Red Fox Inn & Tavern and Teddy's Pizza & Subs so you can get the best taste of Middleburg while you’re here. To see our full list of food recommendations, check out our best restaurants post. If you're traveling on a budget, you can check out our cheap eats post.
Looking for other day-by-day itineraries in Middleburg?
  • 1-Day Middleburg Itinerary
  • 2-Day Middleburg Itinerary
  • 3-Day Middleburg Itinerary
  • 4-Day Middleburg Itinerary
Visiting Middleburg? See our Middleburg Trip Planner.
Feel free to follow our itinerary exactly or tailor it to your own needs — happy wandering!
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Table of contents
  • Middleburg in 5 days
  • Most popular attractions
  • East side of town
  • Off the beaten path
  • Proximity is everything
  • Keep it simple

Day 1

Most popular attractions
For day 1, we strategically grouped the most popular attraction, King Street Oyster Bar Middleburg, with surrounding point of interests to start your trip off with a bang. Combining the average time spent at each location and traveling time in between, it should fill up about 7 hours of your day.
1

King Street Oyster Bar Middleburg

4.6
(1161)
•
4.3
(200)
$$$$affordable
Seafood restaurant
American restaurant
Oyster bar restaurant
Restaurant
King Street Oyster Bar in Middleburg is a popular spot, so it's advisable to make a reservation if you plan on dining in. The restaurant offers an array of fresh seafood, with oysters being the star of the show. You can choose from over 10 varieties daily, sourced from Virginia and Maryland's Eastern Shore. In addition to oysters, the menu features Maryland crab cakes, North Carolina trout, fish and chips, as well as chicken, salad, and sandwich options.
a total pleasure. food is affordable and delicious; lobster roll and blue cheese chips stole the show. monterey chicken salad was also, shockingly good. i ate here on the 4th — a downright american experience.
Lily H — Google review
I stopped in here for lunch on a Sunday afternoon while in town for an event. I was greeted immediately by a hostess. They were a little busy and it was just me so I sat at the upstairs bar. There was some outdoor seating along the building but it was closed at the time - it was a little chilly out that day so I’m guessing that’s why. The bartender greeted me quickly and made me a very good cranberry mule mocktail. The bar area upstairs is small but it’s comfortable. I ordered the lobster roll and had brocolini instead of fries. It wasn’t the beat lobster roll I have ever had but it was good. The brocolini was good. My bar neighbors’ food all looked good as well. The bartender was obviously busy but still attentive and friendly. The atmosphere was casual and upbeat. Prices were comparable to other seafood restaurants I’ve been to. I think this is a VA based franchise and I didn’t realize that at first but after thinking about it I am pretty sure there is a location in Leesburg, VA as well. Overall good experience and I would come again if ever in the area.
Miss V — Google review
The food and atmosphere here were good. You can tell as this place gets really busy! We went for a quick bite at the bar one night and went for lunch the next day. No complaints with the food - it’s exactly what you’d expect. The salmon BLT was good for lunch! My only issue was the host staff. When we walked in they were super rude. I get they were busy but it felt like they could have been a little kinder and not just brushed us off. No issues with our server or the bartender. Both were great and very friendly!
Cassie S — Google review
King Oyster Bar is a true gem for seafood lovers. Their cocktails are excellent — balanced, creative, and a perfect match for their raw bar selections. The oysters are always fresh, and the Parmesan-crusted trout is my personal favorite: flavorful, well-prepared, and beautifully presented. That said, this is very much a seafood-focused restaurant. When we visited with some family members who are devoted meat eaters, they were less impressed, since the strengths here clearly lie in fish and shellfish. If you come for the seafood experience, though, King Oyster Bar delivers consistently high quality and is one of the best options in Middleburg.
Olga N — Google review
Best Ahi Tuna salad I’ve had in a while. Fresh ingredients and a balance of sweet and salt. All dishes we ordered were excellent. Outside seating is very cute. Highly recommended.
Ramzi N — Google review
Nice little oyster bar restaurant in the middle of Middleburg. This is a casual setting. The ceviche is good served with fried plantains. The chili was also pretty good. Portion is pretty small. Fried oyster is delicious here. The grilled salmon sandwich is good with a nice grilled flavor. Margarita was good. The cocktail hell and back is pretty good. It's like a spicy margarita. Crab cake sandwich was pretty good. It was flavorful and fresh.
Thu-Nga M — Google review
Went on a Saturday for lunch, got seated outside on a nice Fall weather, service was quick despite packed restaurant, food was delicious, East coast oysters were very fresh!
Min C — Google review
Wonderful Black folks, the oysters were very fresh and flavorful, but the service was terrible. The gentleman who attended to us was extremely inattentive. I asked him what non-alcoholic drinks they had since the one I ordered was no longer available even though it was still on the menu. He replied vaguely that there were “some,” so I asked if he had Italian soda, since he hadn’t specified the options. He laughed at my question, mocking what I had asked, and replied that they didn’t have it, adding that I had ordered an Arnold Palmer and that it wasn’t alcoholic. When the dishes were served, we didn’t have any silverware it took about three minutes for me to get his attention to ask for some. He came to the table to confirm that there really weren’t any, then finally brought them. When I went to ask for the check, he ignored me, and I had to wait quite a while until he finally came over. When I asked, he said he was busy and told me to wait. When he finally brought the check, he threw it on the table and turned his back. I simply paid and left. It was a very bad experience, especially since I had waited about 50 minutes to have lunch but that part was fine, as the hostess was very kind when she seated me at the counter. Unfortunately, I had a terrible experience at a restaurant I had been really looking forward to visiting.
Eliel V — Google review
1 E Washington St, Middleburg, VA 20117, USA•http://kingstreetoysterbar.com/•(540) 883-3156•Tips and more reviews for King Street Oyster Bar Middleburg
2 min · 0.1 mi
2

Thaiverse Restaurant Middleburg

4.3
(270)
•
3.7
(36)
$$$$affordable
Thai restaurant
Thaiverse Restaurant in Middleburg, located on S Madison St, has gained recognition for its exceptional service and high-quality Thai cuisine. The menu features a variety of starters, soups, salads, and entrees with a focus on authentic Thai flavors. With numerous vegetarian options and an array of spicy curry dishes, there's something for every palate. The restaurant offers an intimate countryside dining experience with attentive staff who provide helpful suggestions.
We ordered the lemongrass Palmer and spicy Thai mule for drinks and both were delicious. For lunch we had Panang Curry (flavorful but spicy!) and drunken noodles with beef and we left with fully bellies and raving about how good it was !
Lindsay F — Google review
Our first time here and it was Amazing ! Late lunch after visiting a friend . The patio was a perfect day to be there, we had a glass of wine, the owner is very friendly and pleasant. We shared the crispy shrimp rolls with an awesome chili pineapple sauce that we truly loved . Hubby had the crab fried rice that he really enjoyed and had some leftover, and I had the spicy eggplant dish , it was the best eggplant dish I ever had and plenty leftover too . We will definitely return on a regular basis :) it is truly a very charming restaurant , if you love Thai , this is the only place to come ! Our compliments to the chef !
Rosa V — Google review
NEVER GO HERE IF YOU HAVE A ALLERGY!!!! I came here because it looked like it was a safe option and like there was a lot of options. (I use a gluten free app that shows me safe options, I have celiac disease) #1 on the menu it says they have gluten-free naan bread and another review that was left on the app for this restaurant showed a picture of the gluten-free naan bread so I ordered it. As soon as it arrived, I was concerned because it looked like gluten bread I asked the server AND the chef they told me it was gluten-free! I went and spoke with the bartender/manager, and I asked him because there was no language barrier with him and he told me it is gluten bread. It is not gluten free. the manager/bartender whoever he is he’s extremely rude. He was so nasty. I called before I got there asking where they were located and he gave me such an attitude “were the only ones in Middleburg so I’m not sure how you’re having a hard time finding us” On the menu it literally says they have gf naan bread (will attach photos) he said “yeah that’s wrong” and I was like are you guys just out or do you not have it at all and he said we’ve never had gluten-free bread but that’s not what other reviews say. He was very nasty and belittling and did it in front of other customers as well he was like “well sorry I don’t know what you want me to tell you this is a mom and Pop shop”. At this point, I didn’t even want to eat anything cause I was so nervous. I asked the server if the rest was gluten-free if she was 100% sure she was not understanding me so I asked her if she could grab him for me. She asked him to come right away, I waited for close to 10 minutes. So I go looking for him bc at this point the food is getting cold and he’s talking to a regular at the bar just having casual talk. He had no intention of coming and talking to me he was not going to. I go up to him and I ask him hey would you mind looking at the two other dishes I got if you can distinguish if it looks like it’s gluten-free or not. and he looked and said “there’s no way to tell I’m just the bartender” but the waitress told me he was the manager. It was a horrible experience. I was very very very excited to come here and I called the restaurant which I never do and I spoke with the owner and he was just like “you know I’m sorry about that. He just has a sense of humor”…I’ve worked in the service industry my whole life, and this man was rude, belittling and nasty for no reason I was very polite. Celiac is not something that I mess around with. Literally just never go here if you have an allergy.
Sienna P — Google review
Updated: 3 years later. Stopped in for Saturday lunch. Service was better & the food was good. We came for a Friday luncheon. Oddly enough they have another Thai right across the street. The service was lackluster, very inattentive, needed several refills that never got attended to, just wasn’t the kind of service we were expecting or lack thereof. We would have gotten dessert but our server wasn’t around to much so never got to ask. The food was ok but was heavily sauced up which lacked flavor. We’ll try again at a later date maybe things will have improved 4/10*
AB R — Google review
Run by a very friendly couple, Thaiverse serves authentic Thai food in the beautiful town of Middleburg. The food is great and will be appreciated by anyone who has been to Thailand and enjoys the cuisine. Amazing flavours, large potions and lots of outdoor seating in the large property. Plenty of car parking close by too.
R H — Google review
Outstanding first experience! We decided to stop by for a late lunch after great reviews from some locals at another nearby shop, and I'm so glad we listened! Food was very fresh, flavorful, and beautifully plated. We started with the Duck Pancake Rolls, and all I can say is wow! A very unique dish made with juicy and flavorful duck wrapped in fresh rice pancakes. SO good! The Pad Thai and Green Curry followed, which tend to be my Thai go-tos, and the certainly exceeded my expectations. Staff was very friendly and attentive, and ambiance is very laid back. Can't wait to go back, hopefully with warmer weather to enjoy their beautiful outdoor area.
Diana P — Google review
The food is excellent and authentic ! The building is historic and really nice.
La L — Google review
HIDDEN THAI GEM Firstly, We came across the owner Piya. She welcomed us with a great smile and assured us of a great experience. The restaurant does give you a very intimate experience of a countryside restaurant. The service was a little slow; maybe that's because we sat on the patio. But, the Owner, Manager, and Staff were great in suggestions. The food was great, except for one or two items. And also served a free complimentary birthday dessert.
Manoj P — Google review
101 S Madison St, Middleburg, VA 20117, USA•http://www.thaiverse.com/•(540) 883-3145•Tips and more reviews for Thaiverse Restaurant Middleburg
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Rooms and guests
Rooms
1
Adults
2
Children
0
Travelers
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1 min · 200 ft
3

Red Bar Sushi and Best Thai Kitchen

4.5
(229)
•
4.8
(33)
$$$$affordable
Sushi restaurant
Nestled in horse country, Red Bar Sushi on Washington Street is a must-visit Japanese restaurant in Middleburg. They take pride in making their own sauces and dressings for salads, sushi, and noodle dishes using the freshest local seafood. The California roll with fresh Maryland crab is a standout dish. The dining experience is excellent with personalized service and delicious food.
Delicious sushi with huge pieces of fish! So fresh! Kiya was especially kind and welcoming!
Tiffanie W — Google review
Great sushi placed tucked out of view in a beautiful little town. The dishes range from tried and true to interestingly creative. I would give them 5 stars, but like much of Middleburg, it's a bit overpriced.
Miranda L — Google review
Middleburg is a joke, if you aren't flaunting your money or driving a $100k car you aren't attended to which is exactly what happened here. We were a party of 2 and the restaurant was empty. We ordered drinks, soups & then about 25 min later the waitress finally came back and asked for our mains. Another 25 min goes by and our drinks show up along with the 3 sushi rolls we ordered. We finished those and she came back asking if we were done so I asked about our mains and soups? She said "oh it got really busy and i lost your ticket". At this point we decided to just cancel the rest of the food because we had already been there for over an hour and a half. The rest of the patrons (assuming mburg locals) were attended to VERY quickly, and received their food almost immediately. Will definitely not be back.
Natasha T — Google review
**I don't recommend this place at all** I was actually on my way to the other thai but I wanted to try this new place. I'm thai food lover and this one was the worst one in DMV. The place was already crowded when I entered the door and I had to wait more than 30 mins to get seated, 8- adults were just standing being awkward. There was no proper host, and 3 servers just taking the order and food. They don't even bother to look at the new customers coming in. **Food took forever to come out !!!!!!! ** Sushi was a big NONO, not really fresh and no taste. Drunken noodle, crispy tilapia, eggplant with tofu were OK. Our papaya salad did not come out so I've informed the lady and she was going to check the kitchen. The cook came out with the salad and apologized for being so late, he also said the salad is on the house since it came out when we finished the food. When we received the check, it was charged. Our table did not mind getting charged and just paid the original and gave extra tips too since they do work hard. But just really bad service and super super super slow. The machine broke down at the end so we had to wait another minutes for credit card payment....ridiculous
Jenna P — Google review
I can honestly say it’s been a very long time since I’ve had such a disappointing dining experience!! While the food itself was of good quality the service was extremely poor and made the visit unpleasant! We sat down and placed our drink and appetizer orders and main dishes a bit later, but about 30 minutes later, our main meals arrived before any appetizers! When we mentioned this to our server, she apologized and said she’d check on it, but another 30–45 minutes went by with no updates and no one checking in on us! When she finally returned and we asked for the check, she asked if we had ever received our appetizers which we hadn’t. We waited another 20–25 minutes with our card ready to pay, but again, no follow-up. Eventually, we walked to the front desk to pay and even then, no one apologized or acknowledged the poor service! It’s disappointing because the food was actually good, but the lack of attentiveness and accountability from the staff completely ruined the experience! We won’t be returning, as there are plenty of other restaurants with both great food and respectful, attentive service!
Dorsa S — Google review
LOVED finding this place!!! They have a great mix of Sushi and Japanese cuisine with a warm and relaxing atmosphere. Worth the drive if your looking for a great casual restaurant to relax at and enjoy really fresh wonderful food.
C F — Google review
I sat down for dinner and it was only my table of 2 and 2-3 other small tables there. I ordered drinks and soups first and then a couple rolls of sushi and an entree shortly after. Only the sushi and drinks show up. But apparently it got busy and our orders were forgotten. So just keep in mind if you’re not a party of rich locals you will most likely be ignored and leave hungry.
Karim A — Google review
This has to be the best Thai and Sushi I’ve had in a very long time. My wife and I got the Drunken noodles, the cherry blossoms roll, the tear drop roll, and the Tonkotsu Ramen. None of or meal options disappointed. My favorite was the spicy drunken noodles with chicken and duck.
Sulaiman J — Google review
4 E Federal St, Middleburg, VA 20117, USA•http://www.redbarsushi.net/•(540) 326-8111•Tips and more reviews for Red Bar Sushi and Best Thai Kitchen
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Where to eat

When you need a food break from visiting all the attractions today, these fan favorite restaurants are about a 1-minute walk away from King Street Oyster Bar Middleburg.

The Red Fox Inn & Tavern

4.6
(636)
•
4.4
(622)
Hotel
Bed & breakfast
The Red Fox Inn and Tavern is a historic inn with comfortable rooms and suites. The tavern features a refined menu along with artwork from local artists. The inn is in the heart of Middleburg, Virginia, where it served as a stagecoach shop, apartment house, post office, butcher shop and hospital.
We hosted our rehearsal dinner at Red Fox and it was perfection. The food was absolutely delicious - our guests raved about every dish - and the tavern room was beautiful. It was the perfect setting for an intimate dinner with our closest friends and family. The staff was so attentive all night, offering guests drinks upon arrival and making sure the entire dinner ran smoothly. It was the perfect start to our wedding weekend in Middleburg and we can't wait to visit for dinner again often!
Nick L — Google review
Great location. First time stay. Great dinner, great service, great location. Room was nice, quiet, overlooking the Mexican restaurant. Struggled with the TV and gave up. Beds really reactive to any movement. Pillows probably too big and hard. Sleeping was a struggle, but I worked it out.
Scott M — Google review
We stopped into the Pub for a light dinner and sat at the cozy bar. The evening was made very enjoyable by our bartender Maria. She made excellent suggestions for our dinner and was quite knowledgeable about various drinks. Her personality was charming and she turned a nice evening into a wonderful experience! We thoroughly enjoyed ourselves, so much so that we told her we would see her again this week. Ask for Maria☺️
John W — Google review
Stay away. Fixed price menu horrible and overpriced for what you get. Appetizer - 1 tasteless meatball; weirdness tasteless cheese + roasted grapes 2nd course, 3rd overcooked char over slimy vegs, and blah dessert. Two of us had 2 course meals, similar reviews. Only good thing was a a la carte order of Brussels sprouts, which was a generous portion. Water not refilled, my friend gave me his when there was no staff to be found, coffee came late, bar drink ordered later came first, carry out leftover box never came, and staff constantly reached over us, including to replace (no kidding) cutlery we didn’t use for a previous course. $500 cost wasn’t worth anything to me. I would have been happier eating across the street. BYW, they’ll say you need reservations. The night we went it was us and another couple with us in the front room. That was it for the room we were in. Update: A manager reached out to me. It was a good conversation and really made me feel better about it.
Nicole C — Google review
We celebrated a birthday at Red Fox Inn and it was a 10/10 experience! One of the best boutique hotels, fine dining restaurants we have ever been to. We staying in one of the garden rooms and had the four course dinner. The staff for the hotel and restaurant were great too. Everything was perfect!
Quinn E — Google review
We had a wonderful one night stay and enjoyed a four course meal at the Tavern. The pre dinner drinks at the pub were great too and love the entire atmosphere of the Inn. Historic and modern. The room was amazing!
Shimul R — Google review
We had a lovely stay at this beautiful inn in a picturesque town. The Red Fox deserves5 Stars, if it wasn’t for the chaos of checking in. No one there, then finally someone showed up, and I was given directions to our room that were inadequate. After 10 hours in a car, I didn’t need to wander for 15 minutes before finding our room.
Andy S — Google review
Once again, an awesome evening at the Red Fox, Night Fox Pub! Our Server, Hailee, was professional and efficient. We initially were seated at a table , which was fine. When seats at the bar were available, Hailee offered to assist us with the move. Hailee is an asset to the Red Fox Inn and Night Fox Pub! Thank you, Hailee.
Judy T — Google review
2 E Washington St, Middleburg, VA 20117, USA•https://www.redfox.com/•(540) 687-6301•Tips and more reviews for The Red Fox Inn & Tavern

Teddy's Pizza & Subs

4.4
(219)
•
4.6
(56)
$$$$cheap
Pizza restaurant
Teddy's Pizza & Subs in Middleburg, VA, is a cherished local gem that serves up mouthwatering pizzas and satisfying subs. This family-friendly eatery boasts an extensive menu featuring a variety of pizza toppings and specialty subs to cater to every palate. In addition to their signature dishes, you can also indulge in fresh salads, tasty appetizers, and delightful desserts—making it the perfect spot for a laid-back meal.
Stopped by Teddy’s for dinner Saturday after taking a little drive to Middleburg because we heard it was authentic Brooklyn style pizza. 10/10 recommend! Not only is the pizza delicious but the environment is so welcoming, Teddy and his staff were so friendly and warm - we will definitely be back!!
Kelly P — Google review
Best pizza I've had to date! The dough is perfect and light. The garlic flavor is incredible but not over bearing. All the ingredients are top notch and the cheese so hot and gooey!!!! Teddy and Family are great people with tremendous heart and character.
Ronnie M — Google review
Teddy’s is the BEST pizza I’ve had anywhere including NYC! The crust is airy and crispy without being over cooked. It’s the perfect crust! The sauce is flavorful and tastes authentic and homemade. The cheese is delicious! It’s not salty and it’s packed with so much flavor. The best part was the impeccable service! Teddy does it all right and really puts others businesses to shame. I can’t and won’t go anywhere else now. I am making the trip to middleburg, again today just for teddys pizza. You must try Teddy’s Pizza!🍕You won’t be disappointed! Thank you so much Teddy & Family!!!🥰
April S — Google review
I was traveling through the area when I got a craving for pizza. I got a slice of cheese pizza from Teddy’s and had a life changing experience. The pizza here is by far the best pizza that I have ever eaten! The sauce to cheese ratio is perfect!! I live in San Francisco currently which has good pizza too but no where as good as Teddy’s. I’m grateful that I took a chance on a seemingly small local shop. When ever I travel back through Virginia, I will be taking a detour to get pizza from Teddy’s.
Nicole A — Google review
My dad and I recently stopped by Teddy’s to try the pizza as we had heard from word of mouth how amazing it is- and it is by far the best pizza I’ve ever had! Teddy and his family are incredibly welcoming and genuine people. We ordered the supreme pizza- very very yummy! I’ll definitely be back to try their other menu items.
Lauren D — Google review
Drove all the way to Middleburg to try Teddy’s (the things you do for food…) and it did not disappoint. While the restaurant is fairly small, it easily accommodated my family and I. The moment we entered, Teddy and company immediately struck a conversation with us. With NY roots, you can genuinely see their love for pizza and how it shines in the way they talk about their cooking process. They use all high-quality ingredients, ensuring each slice isn’t an oily mess like most pies you get elsewhere. In fact, for first time customers they give you one free cheese slice to try to really appreciate how they make their dough and sauce - which we really enjoyed. We ordered a medium-sized meat lovers and it was surprisingly filling - was more than enough for myself and another. They were very generous with the toppings so each bite was packed with flavor. Overall, really liked this establishment, a shame it’s such a trek for us. Though if you’re ever in Middleburg, be sure to check out Teddy’s.
Justin N — Google review
Grew up in NY and this is the best pizza I have had in my 20 years living in Virginia.
Rob C — Google review
You really can't beat Teddy's for an authentic, homey, hole-in-the-wall NY pizza experience. Teddy is second to none on pizza knowledge and passion. His product is the result of his experience and enthusiasm for a great pie. Crispy crust of perfect thickness, vibrant house-made sauce, and the perfect amount of cheese and oil. While Teddy's earns its stripes on the merits of the cheese pizza alone, they'll gladly accommodate a topping and offer many. Granted, if your topping choices are of the Hawaiian persuasion, they may accommodate you reluctantly with the wit and sass of NY pizza vets. We came looking for great pizza but left with a laugh, an experience, hospitality, and fun memories from chatting the counter up while we waited. We will be back.
Charlie H — Google review
9 E Federal St, Middleburg, VA 20117, USA•Tips and more reviews for Teddy's Pizza & Subs
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Day 2

East side of town
For day 2, we recommend exploring the east side side of town. Start the day off with Red Horse Tavern LLC, then wind down and take it easy by the time you get to Harrimans Grill. All together, your day would be filled with about 8 hours of non-stop fun.
1

Red Horse Tavern LLC

4.4
(746)
•
3.7
(195)
$$$$affordable
Bar & grill
Bar
Restaurant
Red Horse Tavern LLC is a popular spot in Middleburg, known for hosting events like the Middleburg Film Festival and Family Reunion culinary event. Situated on W Washington St, it offers outdoor seating where you can enjoy people-watching from the spacious patio. The menu features a variety of options including salads, burgers, sandwiches, wraps, and their popular dish - Fish and Chips.
Great restaurant food was excellent. The shepherds pie was fabulous. No sweet tea but still a great restaurant. Outdoor seating
Nancy — Google review
The food is really pretty good. My favorite dish was the onion rings. The barbecue pork was perfect, not too sweet or too much vinegar. The patio seating is nice. The staff was super attentive and friendly.
C M — Google review
Sat outside on a beautiful sunny cool day. Got the buffalo chicken wrap with side salad. Very fresh and delicious. Staff were friendly (except appeared to be harried). Prices were reasonable especially given the location. We left to walk around the shops and came back for a coffee and piece of carrot cake. Yummy!
David M — Google review
I’ve been here a couple times and they take such good care of me each time. The bar staff especially Katie is so helpful with drinks including nonalcoholic for me and the owner. Sam is so personable and kind! I have celiac disease so he personally made sure that my food was Made in pans that haven’t been used before and took all the precautions needed. I loved that a gluten-free bun was even an option. The food was delicious and I felt great after! Highly recommend.
Chandice P — Google review
The staff are 11/10 at this place, they really make it worth stopping by to enjoy lunch. They were so quick to accommodate our large group, some of whom didn’t speak English, and made everyone feel right at home. Everyone enjoyed the food and never had to wait for a server, there was always someone waiting to help. Can’t recommend enough!
Elizabeth E — Google review
Nachos and bar drink amazing. If you like guacamole then this place is best I’ve had since relocating from California. So similar that I was surprised by the quality. Added chili to nachos and it was a bonus. Great establishment and worthy of stopping.
Jen M — Google review
We ate at the Red Horse Tavern on our first night to Middleburg, then ordered takeout another night. We really enjoyed the overall experiences at this establishment. The service and food were great during our visit. The sandwich options are amazing, which is why we went back for more!
A R — Google review
We waited over an hour for our food and never got it. No one told us how long it would take or apologized for the delay. We could see people after us getting their food. A simple update or apology would’ve made a big difference — very disappointing service. Even if delays happen, good customer service makes a big difference. Offering water, or even informing us of delay. That kind of gesture shows respect for the customer’s time and keeps people coming back. Unfortunately, that didn’t happen here, and it was a disappointing experience overall in our first time being in Middleburg.
Shokouh — Google review
118 W Washington St, Middleburg, VA 20117, USA•https://www.redhorsetavern.net/•(540) 687-6443•Tips and more reviews for Red Horse Tavern LLC
1 min · 200 ft
2

Market Salamander

4.3
(315)
•
4.0
(197)
Permanently Closed
$$$$affordable
American restaurant
Breakfast restaurant
Caterer
Market Salamander is a relaxed market and cafe that offers a diverse menu featuring American and Mediterranean cuisine. The open kitchen serves up breakfast and lunch options, including wraps, sandwiches, and Cinnamon-Vanilla French Toast. The ambiance exudes an Italian market feel with gourmet honey, jams, and wine available for purchase. Visitors can also enjoy a tasting experience at Mt. Defiance Cidery & Distillery before or after their visit to Market Salamander.
Chef Pete is absolutely amazing. I had the pleasure of attending of one of his wine pairing dinner this past Sunday. The food was delicious from start to finish. It was a wonderful atmosphere very welcoming staff and impeccable service. If you are considering attending one of the one wine pairing dinners they have twice a month you will not be disappointed.
Jessica H — Google review
Great local spot in downtown Middleburg with sandwiches, drinks, coffee and fresh pastries. We enjoyed the BLT wrap and the Crab Cake sandwich, all was delicious. Also would recommend their Korean sliders, not too spicy but the sauce is smokey and has some heat. The restaurant is very beautifully decorated to look like a cafe in Europe. Our only issue was the line to order the food eas pretty long and took a while to get the food. The line and cashier to checkout is also in the middle of the inside dining room so we had to make sure we weren't in the way of other customers. Otherwise we had a great experience and the food made it worth it.
Hannah K — Google review
We were meeting up with family to go to a winery, stopped here to pick up sandwiches to take out. While we waited for the rest to catch up we got a snack for ourselves on the patio. A charcuterie plate piled high with delicious finds on it. I was having so much fun noshing away I sort of hoped the rest would be late. The sandwiches we got for take out were equally delicious. This will be a new must stop on my way through town again. Very good fresh food at a good price point. You wont believe how good it is. The staff is very friendly too. They have lots of snacks too. Dont miss this gem. Parking in the back.
Sandy C — Google review
Went for the Caviar and Champagne dinner and it was amazing like always. Chef Pete makes some of the best food and pairs it so nicely with the champagne. The food and wine/champagne always compliment each other and each experience is so unique. Definitely cannot wait for the next one. It is good to enjoy the company of new friends and old friends as Jack says who also makes Market Salamander feel like home.
Lenora S — Google review
Have been wanting to try Market Salamander for a while and finally stopped in for lunch with the family. No table service, you have to order from the front register. However the staff are very pleasant and responsive. The food is what you'd expect from an upscale market, excellent. Had the Jr Club, mac-n-cheese, and the quinoa crab salad. All were fabulous and worth coming back for. If you are visiting Middleburg VA, I highly recommend grabbing a bite or drink here.
Jimmy S — Google review
I have been coming here for years now and every time I come there is something new as well as wonderful consistency about this place. The food is definitely delicious and prepared with such care, you should make yourself a favor and stop for breakfast or lunch. The variety of beverages from sparkling water to regular and specialty refreshments plus their assortment of wines, you cannot go wrong! The ambiance is fantastic inside and the patio is comfortable and clean. Their service is kind and caring as attentive. I recommend this place with my eyes closed.
Belinda C — Google review
Fantastic Food! Recently had the pleasure of attending the "Caviar & Champagne" Wine dinner earlier this month. It was hands down the BEST food and wine pairing dinner I have ever been to - Market's Chef Pete is truly a culinary wizard. Each course was artfully and thoughtfully prepared, inviting guests to marvel not only at each course's unique architecture, but also the delicious design and flavors therein. Many thank yous to the entire team at Market Salamander (you all were extremely professional & polite!) and also to the wine rep for Moët Hennessey for hand crafting a wonderfully whimsical, elegant December event. Truly an unforgettable experience! Highly recommend & hope to attend the next one soon!
Kathleen H — Google review
Love the building & atmosphere, porch has seating around 2 sides, which was also lovely. Was a bit disappointed to learn the menu on google was outdated by 2 yrs so they did not have the sandwich i went there for, tho they suggested something similar. It wasn't bad, but there was very little meat on the sandwich. I felt it was pricey for mostly bread. Staff was cheerful & helpful tho.
Dizzy G — Google review
200 W Washington St, Middleburg, VA 20117, USA•https://www.salamanderresort.com/dine/market-salamander•(540) 687-8011•Tips and more reviews for Market Salamander
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1 min · 200 ft
3

Middleburg Common Grounds

4.3
(514)
•
4.2
(146)
$$$$cheap
Cafe
American restaurant
Breakfast restaurant
Middleburg Common Grounds is a charming local spot on the town's main street, offering breakfast sandwiches and a specialty blend of coffee. It's a popular choice for locals, known for using local ingredients in their menu that also includes local beer and wine. The cafe serves an excellent breakfast and lunch menu, with specially roasted beans for their coffee.
I got the citrus chicken salad sandwich which was FIRE. The ice vanilla latte was also FIRE! I don’t know if it’s because I was hungry but it was so good!! Approved. Also the pricing was perfect.
Misheel B — Google review
Very nice place. Good variety of coffees, tea etc. perfect location for people watching and close to shops
Diana P — Google review
Cute atmosphere for a coffee shop. Cashier was beyond stand offish and appeared miserable. The food???? Well they made the food sound appetizing. However, it was just another microwavable breakfast sandwich. Mushy and tasteless. I expected food to be prepared not microwaved for the cost. Over $20 for two microwaved sandwiches I could have gotten at Sheetz. Disappointing.
Connie R — Google review
This was so disappointing. Saturday noon yes its a busy time but an hour wait for a ciabbatta egg sandwich that was so skimpy with an egg, one thin slice turkey deli meat and a few sprigs of arugula. They dont put prices on anything nor do they tell you how long the wait will be. Cute place for maybe picking up a coffee but otherwise forget it.
Linda W — Google review
What would have been a nice and delicious breakfast turned miserable due to the manager sloppily taking over the whole leather chair section watching extremely loud social media the entire hour we were there. We watched as people walked in and shook their heads at him sitting there and leaving. We knew he was the manager because the staff came over to complain to him and he didn’t even look up to listen. We miss the days when the friendly owners were actively involved :(
J M — Google review
Nestled on the main drag in Middleburg, VA is this delightful quaint coffee shop. The Middleburg Common Grounds has great coffee and lots of outside seating to enjoy your hot or iced Joe while soaking up the morning sun. It’s also very dog friendly with water bowls and treats for your furry friends. The staff is super helpful and nice. The breakfast dishes are tasty but small and leave you wanting a little bit more. All in all, a great spot to grab your morning coffee. The vanilla latte was delicious and had me wanting to go grab another to go!
Brooks P — Google review
Friendly staff and comfy chairs inside. It can get crowded so be patient. I wish they had ceramic mugs for their coffee; adds to the coffee shop atmosphere.
Thomas M — Google review
Dark, cozy atmosphere. Friendly staff. Love the decor. Had a mocha smoothie which was the best I've ever had. Creamy and rich! My wife had the caramel macchiato which which she says was one of the best she's had.
David P — Google review
114 W Washington St, Middleburg, VA 20117, USA•https://www.middleburgcommongrounds.com/•(540) 687-7065•Tips and more reviews for Middleburg Common Grounds
4 min · 0.21 mi
4

Best Thai Kitchen

4.4
(166)
•
4.3
(33)
$$$$affordable
Thai restaurant
Nestled in a charming locale, Best Thai Kitchen is a delightful culinary haven owned by the dynamic husband-and-wife team, Neil and Jamie Metzger. This quaint restaurant offers an authentic taste of Thailand, with dishes inspired by Jamie's upbringing and crafted using high-quality ingredients sourced directly from Thailand. The Pad Thai stands out as a must-try, featuring perfectly cooked rice noodles tossed in a delectable tamarind sauce that balances sweetness and tanginess beautifully.
Our favorite Thai place in Middleburg! Family owned, small business with delicious food being served. Prices are right in the middle, quite a good portion of food, served per meal. Our favorites are the Miso soup and Pad See Ew! Service is OK but not going above and beyond which is kind of sad, as that is something they can easily improve on.
Jan H — Google review
I was excited to try this place having read reviews and based on praise from friends, but it was awful. I asked for “extra veggies” in my Pad Thai thinking it would be more onion and bean sprouts and instead I got broccoli, cabbage and cauliflower. Didn’t taste goo with the flavors of the dish. And the noodles were clumped together and overcooked. My husband’s Panang Curry was almost all sauce, no chicken, and watery. Maybe it’s an off day for them but certainly not worth the reviews I’ve seen. Will not be going back.
Kristin M — Google review
Delicious food, pleasant location and great service. Visited this place over a dozen times. Very consistent in terms of quality and flavors. Both indoor and outdoor seating experience is good. Street parking.
S Y — Google review
This is really a 3.5 rating as opposed to a true 4. But since there are no half star ratings, I’ll let the 4 stand. Ordered the Tom kha (with chicken), Thai ice tea (to cut the heat) and pad see ew (with chicken). Almost all Thai food seeks a balance between the four flavors, which are sweet, salty/umami, sour, and spicy. And depending on the chef, those flavors tend to lean more towards a preference for more sweet, more umami, or more sour. And even when you order a mild level of spice, there is ALWAYS spice present. Thai mild spice is always going to be more powerful than any other cuisine on earth. But we were never asked what level of spice we wanted and the food lacked any sort of heat. We’ve had Thai food in Thailand, Japan, California, Pennsylvania, Maryland, West Virginia, New Jersey, Virginia, D.C. and North Carolina. We’ve always been prompted with our choice of spice level, with exception to Best Thai Kitchen. I’m not sure if their lack of heat in their dishes is catering to the local crowd but it was a big red flag. The Thai iced tea tasted like the pre-made stuff most restaurants buy in a can, as opposed to something freshly brewed. Way too sweet. Tom kha was probably my favorite, although the herbs and galangal sometimes could be sinewy. Loved the flavors overall. My pad see ew noodles were on the gloopy side. Wish they would have charred them better and not added so many extra vegetables. I would have preferred just broccoli, a slice of lemon, and crushed peanuts. Instead, I noticed a piece of broccoli, tons of cauliflower, and shredded carrots. It just seemed very untraditional. Service was just ok. The place wasn’t crowded, but we weren’t really checked on at all until it was time to pay the check. Interesting there is another Thai restaurant directly across the street. I wonder what the story behind that is all about? Was this the best Thai food we’ve had? That we’ve even had in the States ? No…but it’s better than copping out and going some place else for sloppy Italian, burgers, and chicken finger baskets. I think we’re going to try the place across the street next time we’re in the area and compare. Best Thai Kitchen didn’t have much in the way of parking and the other Thai restaurant did. And the entree prices were on the steep side.
Michelle C — Google review
Very calm and peaceful place. The stir fry chicken with pineapple was amazing. Especially the red sauce that goes with it. Nice relaxed service. The food taste good.
Volodya K — Google review
Delicious Thai food Middleburg! Each time we visit vineyards in the area we try to visit Best Thai Kitchen. I feel you get bang for your buck with the quantity of food served and the flavors with each bite you take of the food. The service is great and quick at this small restaurant with indoor and outdoor seating.
Jose V — Google review
This is some of the best Thai food I have ever had the privilege of enjoying. The food is delicious and the service is excellent. If the weather is nice, they have a beautiful outside deck to experience their food. They also have a beautiful indoor dining area.
Rob S — Google review
Loved having lunch here. It was very nice so we sat outside. The food was delicious. Would definitely recommend.
Cindy L — Google review
4 E Federal St, Middleburg, VA 20117, USA•https://www.bestthaikitchen.com/•(540) 326-8111•Tips and more reviews for Best Thai Kitchen
14 min · 0.74 mi
5

Harrimans Grill

4.3
(192)
•
4.0
(235)
$$$$expensive
Traditional American restaurant
American restaurant
Bar
Harrimans Grill is a dining room located in a resort with stunning views of the country and the Blue Ridge Mountains. The restaurant's curving walls are adorned with floor-to-ceiling windows, offering panoramic views of the hotel's surroundings. The menu focuses on farm-to-table and local fare, serving breakfast, dinner, and a lavish Sunday brunch. Despite a mix-up with reservations, guests enjoyed their meal on the pleasant patio while being entertained by wedding parties passing by.
We arrived for a reservation to discover the reservation was inadvertently made for the following Saturday. The staff agreed to seat us outside on the patio. It turned out to be very pleasant setting for a meal. It started to rain, but we were under the overhang and stayed dry until it got very windy -- but only occasionally did we get a little spray. Prior to the rain, we were entertained by wedding parties walking by and enjoyed the scenery. On a nice day, we would definitely want to be seat outside again. The service is impeccable. The wait staff didn't flinch having to walk out during the rain to serve us -- no rush and maintained cordial chatting. When we left, they offered us a complimentary umbrella. Very nice touch! The food was some of the most nicely plated dishes we've had (see pics). I had the Maine Diver Scallops and my wife had the Morel and Leak Fettucine. We both added main lobster. Both entrees were excellent -- certainly, the best Scallops entree I've eaten. My wife loved her pasta and so did I! We chose the roasted Brussels Sprouts which were fantastic. Be forewarned, the portion is very large -- probably enough for 3 to 4 people.
Doug H — Google review
Girls brunch and we all thought it was THE BEST one we have ever had. Our wait staff-Erica and Riley, were so personable, attentive and professional. All of our leftovers were boxed and at our table in a bag. Every single item tasted amazing, we can't even mention just 1 or 2. The presentation, flavor, etc was fantastic. The venue is beautiful, our locals come all the time.
J W — Google review
Having been loyal patrons of Harriman’s Grill at the Salamander Resort & Spa since its opening, we have witnessed a remarkable transformation in recent months that has elevated the dining experience to an extraordinary level. The recent menu overhaul, paired with exceptional service and a renewed commitment to culinary excellence, has made Harriman’s Grill a standout destination in Middleburg, Virginia. The service at Harriman’s Grill is nothing short of impeccable. Our server, Oscar, exemplifies professionalism and attentiveness, ensuring every detail of our dining experience is flawless. His warm demeanor, extensive knowledge of the menu, and anticipatory service make every visit memorable. Equally impressive is the leadership of the manager, Jeff, whose dedication to guest satisfaction is evident in every interaction. Jeff’s ability to exceed expectations creates an atmosphere of genuine hospitality that makes diners feel truly valued. The culinary offerings, under the direction of the new chef, Beni, have reached new heights. The revamped menu showcases dishes that are not only beautifully presented but also bursting with vibrant, complex flavors in every bite. Each course is a testament to Chef Beni’s skill and creativity, delivering a dining experience that is both sophisticated and deeply satisfying. From the first bite to the last, the food is consistently mouthwatering, making it clear why Harriman’s Grill has become a culinary gem. This remarkable evolution in both service and cuisine has transformed Harriman’s Grill into our go-to dining destination. We now find ourselves returning weekly, sometimes twice, as the experience feels like coming home to a place where exceptional food and heartfelt hospitality converge. For an unforgettable dining experience in Middleburg, Harriman’s Grill is unparalleled, and we wholeheartedly recommend it to anyone seeking a world-class meal in an elegant yet welcoming setting.
THE R — Google review
Staff is great here. We had two breakfasts and a dinner here while staying at the Salamander. Every dish was perfectly proportioned and there was a variety of options. Good for one dinner as the menu doesn’t change that frequently and it’s pricey. Definitely don’t miss it though.
Cassie S — Google review
I had a great time enjoying my afternoon at the restaurant and the library. The food was flavorful and the spice level was chef kiss! Service was 10/10. Best ingredients and materials (menu/towel/paper-towel...) only. just an amazing place ... I cant wait to come back
Kyle V — Google review
Beautiful setting on property of the fabulous salamander resort. Perfect if you are staying at the resort and want an evening dinner where you don't need to drive into town. Service staff was very friendly and helped us with our dinner selections, also very accommodating with dietary restrictions. We would recommend the fettuccine entree and the 6oz steak was cooked to perfection. We didn't get dessert because we wanted to order it in the room. Overall we would love to return!
Hannah K — Google review
My husband and I went for our one year wedding anniversary/ ten year anniversary of being together, and we had an incredible experience! The food was delicious, unique, and fun! The server, Anna, was friendly, personable, and attentive. We haven’t been able to stop talking about how special they made us feel and sharing our experience with friends and family. Highly recommend!!!
Amber B — Google review
The business is so beautiful, with beautiful and relaxing deco. The surrounding outdoor grounds is so beautiful. The skilled staff is professional, friendly, and accommodating. The all food was appetizing and delicious. This my fifth time visiting the business and I would visit more if l did not live hundreds of miles away.
Hattie H — Google review
500 N Pendleton St, Middleburg, VA 20117, USA•https://salamanderresort.com/dining/harrimans?utm_source=google&…•(866) 888-5124•Tips and more reviews for Harrimans Grill
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Where to eat

Even the most seasoned adventurers need a break to chow down some food. Close to Best Thai Kitchen, these restaurants are about a 3-minute walk away.

Wild Hare Cider Pub

4.8
(41)
•
4.0
(2)
Permanently Closed
Cider bar
Restaurant
If you're looking for a delightful spot to unwind, Wild Hare Cider Pub is definitely worth your time. This charming venue offers a diverse selection of ciders, ranging from dry to sweet, ensuring there's something for every palate. The friendly staff enhances the experience with their helpful recommendations and warm hospitality. Enjoying a drink on the lovely dog-friendly patio adds to the relaxed atmosphere, making it perfect for both casual visits and special occasions alike.
I think Wild Hare is definitely worth a visit. I was concerned that the ciders may be too sweet for my pallet but several of them were drier than I expected. I thought the gentleman tending the bar was a pleasant personality who gave great advice and I enjoyed the dog in the area and didn't think it was a bother. We brought in a pizza from Middleburg and enjoyed it on location. We will certainly be back again
Paul P — Google review
I absolutely did not enjoy this place at all. I didn’t think the cider was anything special. What really irked me though was the fact that whoever was working there had their dog who kept running over to us and jumping up on us or barking continuously for long periods of time in a small space and the owner did absolutely NOTHING about it. It wasn’t like they were busy at all. She was just hanging out and paying absolutely no attention to her dog. The only reason I gave them two stars is because they had a large selection of games and I was able to hang out with my daughter and play games.
Sahar R — Google review
Fantastic family run business! The ciders taste very natural, not to sugary. Great comfortable couches inside and plenty of outdoor seating options.
Nathaniel M — Google review
This place is so awesome! Bartender was super nice. The front patio is so cute and dog friendly. The chicken tacos were incredible. Took a 4-pack of the Willow, sacksby..... something and something to go. Definitely coming back! Thanks guys!!
Audrey P — Google review
Small tasting room but set up for Covid-19 rules. The tastings were incredible. Rotating taps with new additions.
Clark H — Google review
We enjoyed our visit to Wild Hare, and liked that they had a lot of games. The cider was good, there was a variety of dry and sweet ciders, but a bit on the expensive side. They also ran out of snacks on a Saturday, and there were some pesky fruit flies. We would stop by again though.
Brianne F — Google review
The cider here is excellent. Sit outside or just get a bottle or growler to take home. It's one of my VA favorites. The staff is amazing as well, even when it's a busy night with lots of folks and only one person on staff! It's worth stopping by.
Christopher T — Google review
My wife and I went to Middleburg for lunch on our 5th anniversary. Stopped at the Wild Hare for a drink and food. The food was so simple and so delicious. The ciders were refreshing. Nice atmosphere. Highly recommend you stop when walking by.
Ryan F — Google review
17 E Washington St, Middleburg, VA 20117, USA•http://wildharecider.com/•(703) 402-7956•Tips and more reviews for Wild Hare Cider Pub

CDMX Mexican Bar & Grill

4.3
(103)
•
4.0
(3)
$$$$affordable
Mexican restaurant
CDMX Mexican Bar & Grill offers a unique and flavorful Mexican dining experience. The restaurant takes pride in using fresh ingredients to create their delicious dishes, including the best salsa and chips that patrons can't get enough of. The small and intimate setting provides outstanding service, making it perfect for a special night out. Guests rave about the well-priced lunch specials, strong margaritas, and attentive staff who go above and beyond to ensure a memorable visit.
What a great place! We had Mexican before but never had anything like this. It was out of this world. Everything tasted fantastic. It was bursting with so many different flavors. The salsa and chip was the best we've ever had. We even asked if we can buy the salsa. The owner was so kind and wonderful. She said that they make the salsa, chips and everything they can from the fresh every day!
Grace L — Google review
Do not walk, RUN for the best authentic Mexican food in N.VA (Middleburg, Va). Family owned & operated (mom/aunt are the chefs, cousins are the servers). SUPER friendly. Maria (owner) is young but beyond her years is customer service & a joy to talk to. Food is AMAZING!!! Super fresh and made daily. We didn’t want to leave. DELICIOUS and only Mexican food place we’ll go moving fwd!
Kelly C — Google review
Visiting from NJ, had to try their birria tacos and they didn't disappoint!!! 🤤 The consomme was perfect (not too thin/thick, perfect consistency)! The guac was so good! 😋 Service was excellent as well. Might have to stop by again before I head back home 😎
R. D — Google review
Only had one item chilies verda it was good however they wouldn’t let me sit at a booth, even though this place was largely empty
Joel W — Google review
Outside seating area was great, staff were friendly but food was horrible. No Mexican flavors at all, lack of salt usage, much flavors needed for sure. Overuse of white queso sauce in everything. Taco Bell has more flavor than this place. If you’re looking for a true Mexican dish, this is not the place.
L B — Google review
We came to CDMX Mexican Bar & Grill for a special night out and had an amazing experience. The restaurant is small and intimate, the service was outstanding, and we were blown away by the food. None of us were expecting to get great Mexican food in Middleburg, Virginia. Wow! It was fantastic. Highly recommend it here.
A R — Google review
The food is good and the prices are fair. The margaritas are soft but very pleasant. They have tables outside.The tacos was delicious. A good option and the customer service is good.
Wendy K — Google review
Let me start off by saying if it was possible to give negative stars this restaurant would have negative 10 star!!! The waiter seemed to not be able to handle outside seated guest and inside duties. It took her extremely long times to just out drinks. Every drink we asked about she would say umm I think we can make a Shirley Temple, I think we have sweet tea… I asked for no onion in my food and my first bite had onions in it. I wanted to be sure so I broke the chimichanga in half to see what’s inside and there was more onions. I informed the waiter and told her no need to remake as my wife and nephew food was incorrect at this time and I became extremely disappointed with this restaurant. When the waiter/ server finally came to our table I asked for the manager. The manager comes with the rude attitude and very disrespectfully neglected my concerns. She goes on about how she wasted 3 plates because of my family and how she shouldn’t do anything. I am allergic to onions, my wife asked for ground beef and she had steak with her food along with my nephew. Within manager/ owner conversation with my wife and I she then decided to tell me I don’t have any red bumps or fever so nothing is wrong with me. My wife politely tells her as an owner and manager her behaviour is unacceptable and let us pay and leave. I would never come here again. I do not recommend this place to anyone.
Akram A — Google review
16 E Washington St, Middleburg, VA 20117, USA•https://cdmxbarandgrill.com/•(540) 883-3183•Tips and more reviews for CDMX Mexican Bar & Grill
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Day 3

Off the beaten path
For day 3, if you don’t mind the extra trek, today covers more off the beaten path places like Mt. Defiance Cidery & Distillery. Not quite as popular as King Street Oyster Bar Middleburg, but still highly rated among many travelers. Accounting for getting around and average time spent, today’s activities could take about 7 hours.
1

Greenhill Vineyards

4.1
(385)
•
4.5
(191)
Winery
Food & Drink
Wineries & Vineyards
Greenhill Winery & Vineyards is an expansive property spanning 128 acres, boasting a charming and rural atmosphere complete with natural ponds, a river, and an antique Club House dating back to 1762. The winery offers delicious wines produced exclusively from Virginia-grown grapes such as the classic Chardonnay, Cabernet Franc and Meritage blends. Visitors can also relish in their savory Charolais beef and honey harvested from their own apiaries.
Great view and location. Near the Middleburg town center where there are lots of restaurants and antique stores to explore. Their Italian plate was one of the best I’ve had! Amazing service as well. Staff were very friendly and kind. Highly recommend.
Michelle K — Google review
It’s 21+ but theres several signs posted. The grounds were stunning! All the staff were super friendly and helpful. And their wine was so tasty, we wound up taking some home with us. Would definitely return
Zachary S — Google review
Very pleasant first visit. Lovely setting and appreciate the indoor/porch/outdoor seating options. Wine was very good and all Virginia-sourced, though we found it pricier than other Virginia-sourced vineyards. Did a tasting then each had a glass of Viognier and Merlot. We had the Italian Mezze and Beef Pate plates and they were beyond delicious. Will certainly be back.
Derek R — Google review
Fantastic views. Wines great. I enjoyed the superstition red blend and the Pinotage. Got to see some harvest. Very fun.
John F — Google review
What a fun winery. Our tasting was with Emma who was knowledgeable about the making of the wines and their grapes, but also very engaging. They have a great selection of wine with your traditional Virginia varieties, but also some creative blends. It is in a lovely pastoral setting. We left with a couple of bottles of wine and a candle. They have candles burning in the restrooms -such a nice touch- and bonus, you can buy them. We highly recommend stopping by if you are in the area. We will definitely return.
President — Google review
We have been members for quite a bit now and I love Greenhill! We live in Arlington which can get busy and loud, and this winery is an escape for us and that is made possible with their nobody under 21 policy. This place is also dog friendly outdoors which is awesome! The staff is friendly and recognizes us when we come in and greets us. The complimentary tasting is great because wines taste different depending on the year. You can do a tasting and after get a glass a wine so you don't have any surprises when it comes to taste. The bathroom is always clean and has burning candles which is a nice touch. I love their wine and I think that the price point is fair especially if you are enjoying the wine at the winery. The view is stunning, it's quiet, large outdoor space, food is available to order, nobody under 21and they limit parties of 10+. Most of the negative reviews on here are because of the nobody under 21 rule. I find that odd since there is signage all over the property, it is on their website and on their socials. It's also common for wineries to have this in place. Some complain about the 10+ rule which is also on their website and socials. Most places that are not huge chains have that in place as well to assure that they have appropriate staff and space. Some are about bad recommendations which is also odd because everyone has different preferences when it comes to wine and the staff has always helped me and offered to taste something when I am specific with what I am looking for. Anyways, if you at least google the place you will see all that needs to be known and pictures of the venue. It's not a party/loud winery and its not a kids friendly winery. Which to me are selling points :)
Jasmine G — Google review
The foods and tasting are AMAZING. The atmosphere is warm and inviting. You can not beat the mountain view.
Amanda G — Google review
I really appreciate the scenery and the quiet, hence why they have “no children allowed”. Huge bonus!!!!!!! This is a place to get away from noise of all sorts. Pupper friendly place. The drinks are good and the food is fantastic! Try the mozzarella and the olive oil balsamic dip! They have heated areas outsides on the porch and mini fire pits! This is my 2nd coming and I’ll be returning! Get there early so you can get the best seats. Seat yourself to any table available type of arrangement.
A C — Google review
23595 Winery Ln, Middleburg, VA 20117, USA•http://experiencegreenhill.com/•(540) 687-6968•Tips and more reviews for Greenhill Vineyards
4 min · 1.5 mi
2

Mt. Defiance Cidery & Distillery

4.6
(227)
Distillery
Cider bar
Event venue
Located in Loudoun County, Virginia, Mt. Defiance Cider Barn offers a unique experience for cider enthusiasts. The barn produces ciders made from locally sourced apples that are bursting with flavor, such as the Raspberry Peach and Blackberry ciders. In addition to ciders, the barn also offers a robust variety of spirits, including an agave flight that is a personal favorite for many visitors.
We had a large group of people meet for a social event. The GM and staff were very friendly, accommodating, and provided great customer service. The food truck served delicious German food. Even though the band canceled at the last minute, the management helped find a wonderful replacement.
Seth C — Google review
If you like cider and are in middleburg add this to your stops! The cider is good and they off decent flights. I really liked how they take classic drinks like sangria and a shandy and add their own cidery twist on it. They have a great outdoor area to sit and drink in. There’s also a cocktail section we didn’t try that id love to go back to.
Cassie S — Google review
Very nice atmosphere and drinks, and best of all were the wonderful staff! The cider offerings included a surprising selection of cocktail-like flavors- I'm sure anyone would could find a varietal to enjoy. Afternoon music was provided by a talented singer/keyboardist who nicely set the tone for our afternoon event. Highly recommend.
Gary — Google review
I enjoy our tasting here and they have so many different flavors. Would love to come back to try their fall ones!
Kyle V — Google review
Beautiful building in a great location just past the downtown. The gentleman at the bar was extremely knowledgeable. You could tell he loved the world of cider, mead, and wine. It was a Sunday. A musician was playing out back, he was very good and it made the whole atmosphere so relaxing. Sipping cider while watching the leaves fall was magical. Great food truck that day serving Asian cuisine, and it was yummy! Nice place for events!
Robie — Google review
An absolute gem! Incredible cider with a wide variety that goes beyond delicious — every sip was amazing. The space is both classy and welcoming, with gorgeous indoor and outdoor areas, dog-friendly (our pup loved it!), and even perfect for our twin babies. Great climate control inside or sunshine outside. Fantastic food truck, tons of parking, ideal location, and the staff were genuinely kind and respectful. A place that brings people together and creates real memories. We can’t wait to come back!
Michael W — Google review
We brought the kids. Distillery seating is only in the outdoor area. The liquors are not the highest quality. Only one of 3 was ok. We did two different flight combos. The cocktails were definitely much nicer - we got one. And the bartender was extremely friendly and helpful. The location and set up is nice. The live music played great songs but the noise level was deafening for the small venue size and space. It definitely ruined the experience and we all rushed to finish up quickly and left with headaches. Since the band set up in the restricted distillery area there was no where to go to avoid the loud music. Other guests were also upset with this set up. It ruined an otherwise great experience at an average tasting distillery. We didn’t go or drink at the cidery but the ladies there weren’t the most pleasant as we navigated our options. Could see ourselves going back but on a date without live music.
Charles B — Google review
I just didn’t get the appeal of this distillery and cidery. For some reason you can taste the ciders inside but have to go back on the back porch to sample from the distillery. I think we had a new person at the cidery side because she knew practically nothing about what she was serving. And, although she was not there alone (two other people there) she was given no guidance or help for our group of 8, all doing a full tasting. None of us tasted from the distillery because when we went back there we were greeted with such a cold shoulder that there was no way we would pay them anything. Given what we experienced, tt is no surprise to us that in the late afternoon on a weekday we were the only people there. We liked some of the cider fine, but none enough to make any purchases.
Ralph B — Google review
495 E Washington St, Middleburg, VA 20117, USA•http://mtdefiance.com/•(540) 883-3176•Tips and more reviews for Mt. Defiance Cidery & Distillery
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8 min · 0.39 mi
3

Tremolo Bar

4.6
(131)
•
4.5
(11)
Restaurant
Tremolo Bar is a popular wine bar known for its small plates and upscale atmosphere. It offers a variety of tasty tapas and cocktails, making it an ideal spot to start the night with appetizers and drinks. The restaurant has a clean and aesthetic ambiance, resembling an upscale tasting room. While the menu may not be extensive enough for a full meal, it's perfect for enjoying light lunch or dinner options.
Food and beverages were fantastic! My husband enjoyed several glasses of wine recommended by Joe who hit the mark each time and tailored it to our dishes. I had the gin and tonic which was one of the best I’ve ever had. Each dish was delicious. We had the scallops (favorite), lamb meatballs, tomato bread with anchovies and jamon. Great place.
Rachel R — Google review
If you’re staying at the Salamander and need to change up the food, look no further than Tremolo. It’s small dishes that are fantastic. Would recommend the stracciatella, the lamb ragu and the Moroccan carrot salad. Both were fantastic. The staff was great and super friendly too. I started with a cocktail — a bees knees — and for my second drink switched to wine. The server made a great recommendation for a light red that went with everything.
Cassie S — Google review
Visited for the first time today, am sure will be visiting often. Curated and personalized experience with food and with hospitality. These guys know how to take care of you. Food tasted fresh and flavorful. Labneh had the right consistency, pita was airy and the cucumber salad had delightful spice notes.
Garvit S — Google review
Food was pretty mid. Here’s what we had and our ratings: 1) chips and dip - chips were ok 5/10 - dip wasn’t bad at all 7/10 - in all: 6/10 2) Pan con tomate - bread was so soft and crunchy at the same time - sauce was very flavorful - in all: 8.9/10 3) lamb meatballs - sauce was very unappetizing - meatball itself had an uneasy texture - it could’ve been because my palette is a little different from the food style but it was very hard to eat - in all: 1/10 4) shrimp roll - shrimp wasn’t bad - bread (shrimp stuffed in bread) tasted like canes bread, no complaints - in all 5.4/10 5) hanger steak - steak was cooked perfectly (medium rare - rare) - sauce was pretty good - easy to eat, small bites - in all: 8/10 6) ribs - sauce was quite spicy - ribs were easy to eat - cooked well In all: 7.6/10 7) Pom spritz drink - was very hard to drink - took one sip and had to change it - again, probably just too rich for my taste but the after flavor tasted like how your throat feels after throwing up 😅 - in all: 1/10
Margot — Google review
My sister and I have been coming here since it opened and have enjoyed every bit of this place -- the food, the wine, the cocktails, and the atmosphere. I recently brought my husband here and our server, Joe B., did an excellent job! We ended up getting an off-menu crafted cocktail, the yellowfin tuna crudo, and a glass of Albarino. It was the perfect small plate, and exactly what we were wanting on a warm sunny day. This place is on the pricey side, but well worth it!
AJT — Google review
The experience at Tremolo was excellent! The food, the wine, the cocktail, and the cheerfully helpful service! We thoroughly enjoyed our afternoon in their patio with our pup. We plan to be back to taste more of their exquisite bites!
HP — Google review
The kitchen at Tremolo Bar deserves nothing but praise — 5 stars for creative, flavorful, beautifully executed dishes that could rival any top-tier restaurant. Unfortunately, that brilliance stops cold the moment the plates leave the kitchen. The waitstaff is, without question, the least friendly we’ve ever encountered. No warm greeting, no check-ins, no sign they cared whether we enjoyed our meal — they barely tried at all. Every server and the person at the front looked glum. Service was so indifferent, turning what should have been a stellar dining experience into a frustrating one. Tremolo Bar’s food is outstanding, but until the front of house matches the kitchen’s excellence, the overall experience falls flat. Overall: The rude staff and horrible service are enough to make us never return again.
K C — Google review
Our group of three friends had an amazing lunch at Tremolo. Beautiful food and lovely wine selection. The beets and yellowfin crudo were fabulous.
Aimee B — Google review
19 E Washington St, Middleburg, VA 20117, USA•https://www.tremolobar.com/•(540) 687-5784•Tips and more reviews for Tremolo Bar
1 min · 100 ft
4

Cuppa Giddy Up

4.5
(127)
•
4.6
(36)
$$$$cheap
Coffee shop
Cuppa Giddy Up is a delightful family-owned café nestled in the heart of Middleburg, where coffee lovers can indulge in organic fair-trade brews and specialty drinks. With over 15 years of experience, this cozy basement shop offers a warm atmosphere perfect for enjoying a decadent Raspberry Mocha Dream or a comforting cup of Columbian Organic coffee. Pair your drink with fresh bagels from Ashburn Bagel Shop or treat yourself to delicious pastries like the pumpkin cheesecake muffin.
Delightful experience and a must-do. It's like taking a mini vacation. You step into a historic building complete with beamed ceilings and brick floors, and come out with the most delicious coffee you've ever had. They create unique coffee concoctions, and their whipped cream is so good that you could eat it for dessert (and people do). The pastries are always perfectly fresh. The owners are kindhearted people who are an important part of the community. Can't say enough about this wonderful place. Bring your dog, step in for an indulgent coffee, and sip it while you stroll around the beautiful streets of Middleburg.
L. L — Google review
This cute little bakery/cafe has is located in the basement level just a few steps down from the Main Street in Middleburg. There’s a small selection of locally baked treats and drinks including coffee, cappuccino, etc. Prices are comparable to other bakeries in northern Virginia.
Holistic G — Google review
The people running this coffee shop are really trying their best. If they were in the game Overcooked, the kitchen would have burned down and and Kevin would be really upset. They seemed disorganized and struggled to make orders correctly and efficiently, and seemed annoyed with customers when they let staff know their drink was incorrect. Cleanliness of the cups/lids was concerning. Some of our drinks tasted watered down. I think they have a lot of potential, but they need some additional training and/or support. Since I waited 20+ minutes for my drink, I observed quite a bit.
Jessica R — Google review
Cozy cafe good hot white chocolate and peppermint latte; no wait on line, no Apple Pay, cash or credit
Divina V — Google review
They brew a yummy cup of coffee! They have specialty drinks listed on top of the glass counter, and I wasn't disappointed by any of them. I highly recommend visiting, just know there's very little seating. They're also in the basement, so don't try the upstairs ;)
Jeremy L — Google review
From the main street, its hidden by being below ground level. A small flight of stairs but well worth a visit. The barista is friendly and there are plenty of coffee and pastry options for all patrons passing through.
Vin 0 — Google review
Had the pleasure of discovering this place earlier today it's a small easy to miss literal "hole in the wall" but when you enter it's a cozy little shop with really good pastries and baked goods the pumpkin cheesecake muffin was awesome. The hot apple cider reminded me of a warm slice of apple pie and the owner is super nice and talkative, also very clean! All in all its a nice quick cup of coffee or cider and a muffin. Do yourself a favor and swing by.
Will A — Google review
What a charming "hole in the wall" (it's actually like a little cave"). Great coffee, tea, and smoothies plus the lone fella working there was really nice. We need more places like this and fewer Starbucks.
Marc N — Google review
8 E Washington St, Middleburg, VA 20117, USA•(540) 687-8122•Tips and more reviews for Cuppa Giddy Up
2 min · 0.12 mi
5

The Upper Crust

4.5
(132)
•
4.3
(91)
$$$$affordable
Bakery
The Upper Crust is a family-friendly pizzeria and bakery that offers a variety of delicious treats in a simple setting. From inventive pies and oven-roasted sandwiches to an array of baked goods including pies, bars, buns, cakes, croissants, and the popular Cow Puddle. Visitors rave about the "Rosy O'Grady" pie which combines cherries, blueberries, and peaches with perfect crusts.
Have happily been Eating at the upper Crust my entire life 31 years, and before this it was Huckleberries as well. Always fresh pies, cookies, deserts. Sandwich’s for breakfast and lunch, but make sure your early or you might miss your favorite, Sausage Egg and Cheese Croissant does me just right!
Flokie L — Google review
I really like this tiny, quaint bakery! my boss loves their cow puddles, so typically we end up getting a ton of them at a time. located across the street from the Safeway, this little bakery now takes credit cards via Square & cash. super convenient for me now as I don't have to take cash with me anymore. I took a ton of photos, but I didn't realize until afterwards, they have a sign that said no cell phones :x sorry! their baked goods are always good. cow puddles are these chewy, addicting cookies made with some decadent brown butter. I also bought a honey bun for myself and a sugar cookie for my daughter. she really enjoyed it as it was a cute little purple horse! the chocolate croissants were so good. I wouldn't compare them to an actual French one, but good for what you're getting. I honestly had to stop looking as I wanted to buy everything myself (pregnancy cravings). great little stop for anyone in the area!
Allie G — Google review
What a cozy little hidden place. Glad thar we found it just happened to walk by. All were very cheap and all bakeries that we bought were good especially their croissants. They just melt in your mouth. They were buttery and so soft, just the way we like it.
Grace L — Google review
The sausage rolls are amazing. Their sourdough bread is yummy and their cookie are good too
Ashley S — Google review
Delicious simple food and deserts. Everyone is always friendly. The old building gives you that early 1800 feel. Love this place.
John — Google review
Cute quaint tiny place, good food... if the staff had a smile or better attitude it would have brightened the whole experience..
Misty — Google review
Went in to get 3 sandwiches and young lady decided that she “didn’t have time” to make the third sandwich which is pretty bizarre to me considering it was a grilled cheese by any means didn’t know a grilled cheese took longer to make than a hot turkey club but that’s just me I guess
Kyle F — Google review
Great local bakery; everything is freshly baked! Neighborhood gem
Divina V — Google review
2 N Pendleton St, Middleburg, VA 20117, USA•(540) 687-5666•Tips and more reviews for The Upper Crust
3 min · 0.14 mi
6

Mt.Defiance Cidery and Distillery

4.6
(127)
•
4.5
(40)
$$$$affordable
Distillery
Food & Drink
Cider bar
Located in Middleburg, Mt. Defiance Cidery and Distillery offers a modern, spacious room for tastings of their local ciders and spirits. The distillery's barn location allows visitors to sample dry cider creations, while their smaller tasting room in the heart of Middleburg's Main Street features liquors like rums, apple brandy, and Virginia's only absinthe. Additionally, the establishment provides outdoor seating with a pleasant view of downtown.
My wife and I visited the distillery and enjoyed two three-pour flights. Each of our choices was delicious, and the server made the experience a fun and informative one. We bought a bottle of the Straight Bourbon Whiskey to take home, and it was smooth and delicious. We highly recommend a visit to Mt. Defiance.
Tim G — Google review
I stopped in to try a cider on a Sunday early afternoon while in town for an event. I was greeted immediately by the bartender. She was friendly and personable. She helped me pick a cider - I didn’t want to do a whole flight because I was traveling - and I am not actually sure which one I tried. I know it wasn’t the farmhouse but I can’t remember. Regardless, it was very good. They have some tables sectioned off outside in the parking lot. I sat out there and enjoyed the cider. I got a small bottle of whiskey to take home. I haven’t tried that yet. This was a quick stop but very good. The parking lot is tiny but there is street parking and several lots in Middleburg. It’s a very walkable town.
Miss V — Google review
This smaller location downtown is convenient for grabbing a delicious cider while exploring beautiful Middleburg. The lovely lady helping us was patient and gave us great recommendations. I had the Shandy. It was light and refreshing! Seating inside and out, clean restrooms.
Robie — Google review
Love this place! Their cider flights are great. There are rotating flavors along with the classics. The sangria, which may have been a summer seasonal drink, was also very good. The staff is so friendly and helpful. I have no complaints.
Caroline — Google review
Went to both places. Very different vibes but both well worth the visit. Be forewarned. This distillery in town in small. There's outside seating too but if it gets crowded, it is crowded. That said, both are so enjoyable. Staff is very friendly. The cider at the Barn is just right for the fall and winter. Lots of different tastes. Lots of choices. The cocktails in town were also very enjoyable. Well worth the flights if you aren't sure what you want. The Barn is scenic. It wasn't crowded on a cloudy a October Sunday, which was nice. I drove out from University Park, MD, and it was well worth it.
Michael B — Google review
Went to Middleburg from Harper's Ferry WV specifically to check out Mt. Defiance for my birthday with several friends. The Cider Barn was large and accommodating. I had a strawberry slush and tasted many of the other ciders they had from friend's flights. I'm not a super fan of dry cider, but they had plenty of other options as well. My slush was amazing and the food truck had the best falafel we had ever eaten. We decided to move to the Distillery as we were excited at the spirit flights and many options of on premesis made spirits. As others have said, parking is very limited, but we solved that issue by carpooling from the cider barn. I honestly wish we would have just stayed there. The atmosphere is much much different at the distillery. I'm not sure if the woman working the counter was having a bad day, but she was very curt and disinterested in us and we quickly felt like we didn't belong there. We finished our drinks, bought a few bottles, and left to finish out the evening at the Oktoberfest event down the street. My friends and I are all in our 30s...and a couple were actually in their 60s that went be fore us and said they had the same experience, so I have no idea what prejudices our group could have stirred up aside from being "out of towners". We probably won't be back to the distillery. Cidery on the other hand is a must go if you are in town. Might even consider the hour drive to go back there again.
Amanda P — Google review
Nice location that is walking distance to downtown Middleburg. Clean place with delicious cider and very friendly staff. Also has a nice outdoor area.
Barbara T — Google review
I visited the small one downtown. Great Service, both folks were just chock full of information about the brews and the local area. We started off with the Cider sampler - Old Volstead, Farmhouse & Apple Pie; for me the Apple Pie cider won hands down and I ended up leaving with a growler of it. Next, we re-crossed the DMZ and tackled the spirits. I had the Absinthe flight; first up was the Agave Spirit, good, but burned like hell on the way down; next was the Cassis Liqueur, awesome also and bought a bottle to take home; Finally, the Absinthe – Awesome. A nice place to visit
Larry A — Google review
495 E Washington St, Middleburg, VA 20117, USA•http://www.mtdefiance.com/•(540) 883-3176•Tips and more reviews for Mt.Defiance Cidery & Distillery
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Where to eat

Under a 1-minute walk from Tremolo Bar, here are a few close by recommendations for when you get hungry exploring around.

Middleburg Deli

4.6
(209)
•
4.4
(8)
Deli
Located in the charming town of Middleburg, Virginia, renowned for its upscale shops and historic architecture, Middleburg Deli is a popular sandwich shop that embodies the essence of the region's hunt country. Situated in the compact downtown area, this deli offers an array of delicious sandwiches that are sure to satisfy even the heartiest appetites.
This place is so cute and small and seems like such a hole in the wall kind of place but it’s always busy and such a hot spot- for good reason too. The sandwiches are so amazing! Everything is fresh and warm and you can’t order a bad meal. We’ve been to visit Middleburg a lot this year and can never leave without stopping by!
Hannah C — Google review
Love stopping by the deli when we’re in middleburg. The patio is cute and the food is amazing. They have so many options. Wanted a simple turkey sandwich today but the chicken salad and Cajun chicken are also very good.
Samantha R — Google review
Great deli with lots of options. Had an egg salad sandwich and it was delicious! Nice patio for outdoor dining. Will definitely stop again.
Jennifer R — Google review
First time here. Was recommended a half and half chicken sub / steak and cheese. Very well made, tasted excellent. Would highly recommend.
Andrarict — Google review
One of the best Grilled Chicken Sandwiches of my life!!!! The Cajun Chicken was absolutely out of this world! Either a quick bite to eat or a long lunch, the patio here is one of my favorite spots to sit on main street in Middleburg. Stop by any time for an amazing lunch or quick snack, the menu is so expansive, you’re guaranteed to find something to fit every taste.
Colby B — Google review
Just a sandwich place without any particular star of the show. I ordered a Buffalo chicken sandwich and was served a simple fried chicken filet on a bun with hot sauce. I was disappointed with the lack of gourmet and deli-like dishes. My order-taker had no enthusiasm and offered no suggestions. They appeared to not know how to describe their dishes, thereby discouraged any questions about the food. I'm pretty sure I won't return.
Mommy T — Google review
My family and I come here every Saturday! They let you build your own sandwiches, and Sebastian always helps us make the perfect combo :)
Scarlett A — Google review
It’s a great place on a side street in one of the most prestigious parts of the county this deli is sticking to its roots for the people giving out amazing quality sandwiches, soups and salads for an amazingly tasty price… 10 out of 10 would come again as well as recommend..
Ashby M — Google review
2 N Liberty St, Middleburg, VA 20117, USA•https://www.middleburgdeli.com/•(540) 687-3456•Tips and more reviews for Middleburg Deli
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Day 4

Proximity is everything
For day 4, we bundled attractions like Lost Barrel Brewing and National Sporting Library & Museum and other places within a close range, so that the time it takes to travel between all of them is less than one hour. Combined with the average time people spend there, your day should take about 7 hours.
1

Lost Barrel Brewing

4.7
(360)
•
5.0
(15)
Brewery
Event venue
Live music bar
Lunch restaurant
Lost Barrel Brewing is a popular destination for adults, offering a unique selection of hand-crafted beers and hard seltzers. The Bale House, a restored two-story barn, provides event spaces including the Loft with views of the brew room. Their Loco Kitchen serves artisanal dishes made from fresh seasonal ingredients to complement their beverages. Visitors can also enjoy dining on the picturesque porch or in the tap house while taking in the beautiful countryside surroundings.
Perfect place to be around friendly people, good drinks and food! And music for sure ! We there for Saturday afternoon ! The kids like it as the food was as they like it For me! The beer collection nice and specially Ryan and October-feast! The weather helped a lot ! Sunny and nice The prices are decent and very reasonable ! The staff are very friendly. Clean space for sure ! Totally was a positive visit and recommend it for groups and families with kids
Zed A — Google review
I had anniversary party for my friend this past weekend . Just wanted to say thank you to Natalie she did a great job helping with the reservation for the Saloon . Everyone was very friendly I’m very happy with the service . Leo and other staff were always on time with the orders, I really recommend .
Patricia M — Google review
The Frozen Summer Breeze was so delicious! My friend & I shared the pot sticker & the humus/pita - all very yummy. The pita was nicely baked with a slight crispness to it. The venue is gorgeous! We'll definitely be back & will bring friends!
SL R — Google review
We stopped by Lost Barrel Brewing over the weekend during a day trip to Middleburg and had a fantastic time. We sat outside with our dog on a leash, and it was the perfect spot to relax. The staff were friendly, and the service was quick and attentive. As we walked to our table, we passed a group who made loud passive aggressive comments to themselves about dogs being allowed. It was rude and honestly surprising, especially considering how welcoming and dog-friendly the area usually is. Ironically, their kids were the ones running around and yelling. Fortunately, that was the only negative moment, and everyone else around us was lovely. We tried the hummus, which isn’t something we normally order when going out, and it really impressed us. Fresh, flavorful, and a great pairing with our drinks. Overall, this was a great stop during our day in Middleburg, and we’re already looking forward to coming back.
Steven B — Google review
I chose Lost Barrel to host my husband’s surprise birthday! Reserved the Saloon and the Studio! Worked perfectly for our group! Food, beverages and atmosphere were great. Most guests were first time attendees and they loved the venue!
Amy C — Google review
Enjoyed another visit to Lost Barrel Brewing last Sunday listening to Shelly and the Mud Cats. LBB has good facilities and the beers were refreshing.
P ( — Google review
Been coming here since they opened. It's by far the best brewery close to nova, they have great food, great beer, and great service. The wild berry sour is awesome.
T B — Google review
I came here for the first time this past weekend and really enjoyed myself! It’s much prettier than most breweries are- inside and outside were both lovely. The beer was great, great food options, and the staff was very friendly. Also they have great merch!
Laura M — Google review
36138 Little River Tpke, Middleburg, VA 20117, USA•http://lostbarrel.com/•(540) 326-4631•Tips and more reviews for Lost Barrel Brewing
4 min · 1.5 mi
2

National Sporting Library & Museum

4.8
(85)
•
4.5
(62)
Art museum
Museums
Specialty Museums
The National Sporting Library & Museum in Middleburg is a small yet delightful museum that showcases paintings of horses, dogs, and other elements associated with the town. It's a perfect addition to your weekend plans and offers a wonderful respite from indulging in food and drinks. As part of the town's dedication to equestrian culture, the museum preserves and promotes historic sports that define Virginia Hunt Country.
Drive from Alexandria to this Middleburg location only to see the Secretariat monument/bronze statue. Was able to go into the library and hear some of the presentation. Driving through the town, it's very charming and has a lot of nice little shops and restaurants. Want to come back when it's cooler just to stroll along the main road. Thank you for hosting this historic event.
Daleena B — Google review
Gallery was spacious, peaceful, and I could enjoy the great artwork free of crowds. Library was even better! I had a great conversation about some of their most treasured books, and then I picked a 1897 copy and read for a while. Gem!
Aida C — Google review
Some of the exhibits are closed now so the price of admission is half price and free for kids at the museum. The artwork was interesting; the plaque descriptions were very informative. There is currently a special exhibit of Secretariat downstairs in the library that has horseshoes showing how long his stride was that was pretty neat along with other cool (more contemporary) pieces. The library had some really great kids books we sat and read for a bit. Highly recommended (also with kids).
M — Google review
Off the beaten path. Great exhibits, but the current showcase is called Identity Restraint: Art of the Dog Collar which is very informative. A one of a kind museum that you must put on your calendar if you're visiting the Salamander Resort and Spa or Middleburg.
Brian L — Google review
Beautiful building and grounds, amazing staff. John Connolly, the "George L. Ohrstrom, Jr. Librarian" is a spring of knowledge. I had the opportunity to be invited to see the rare books collection and it was amazing. Even if you don't like fox hunting or horses you can still appreciate the art and passion for the sport that is shown through this collection. Or just visit to enjoy one of the most elegant public libraries you probably will ever go to. I only had time to visit the Library, but when I go back I will take the time to visit the museum as well. There is an $10 admission fee for adults, $8 for seniors and teens, and children under 12 get in free.
A S — Google review
came on a snowy saturday. Nicole at the front desk was friendly and explained the exhibits and points of interest in the museum. museum entry was $10 and the library was free. she directed us to the library and the book on the japanese fox, kitsune. valerie at the library showed us to the book and welcomed us to the cozy reading room. the staff was extremely friendly.
Evan H — Google review
Nice set up. We walked through both the library and the museum. Allow about 2 hours.
Gerry E — Google review
Great little museum. The kids really enjoyed it. The library was beautiful too.
Tarataffy — Google review
102 The Plains Rd, Middleburg, VA 20117, USA•http://www.nationalsporting.org/•(540) 687-6542•Tips and more reviews for National Sporting Library & Museum
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1
Adults
2
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0
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2
4 min · 1.1 mi
3

Boxwood Estate Winery

4.3
(196)
•
4.0
(116)
Winery
Food & Drink
Event venue
Wine store
Wineries & Vineyards
Boxwood Estate Winery in Middleburg, Virginia comes highly recommended for a lovely and relaxing experience. The outdoor seating is perfect for enjoying the beautiful grounds, while the indoor facility offers a chilly but enjoyable atmosphere. Visitors praise the high-quality Virginia wines that are free from additives, making it a great choice even for those sensitive to such elements. The warm welcome and excellent service from the staff add to the overall experience.
This was our first visit f to Boxwood and it was amazing! Carolyn gave us a great tour of the grounds and their winemaking process which was fascinating! Erin’s tasting was awesome and so informative of all of their wines. We couldn’t get enough of the 2019 Topiary! DELICIOUS!!! We had a yummy lunch and all around fantastic afternoon at Boxwood! We can’t wait to go back!
Christina D — Google review
Had a great tasting here. We did the wine + cheese and charcuterie board tasting. Each wine was unique and they had a good selection of whites, a rose and reds that all paired perfectly with their cheese selection. I really liked the trellis. After we had the chance to check out the actual site and see the cave where you can do a tasting. Looks super romantic!
Cassie S — Google review
Wow! I wasn’t sure what to expect from this place. When I got there, I thought it was gonna be kind of pretentious. My friend and I did a tasting in the barrel room, and I thought that was gonna be pretentious. However, it was amazing. Mark did our tasting and he was so knowledgeable and so friendly and so informative and didn’t rush us. The wines were amazing. There was not one I did not like. My friend loved the Sauvignon Blanc. We ended up sharing a bottle of the Boxwood which was so delicious. We got to talk to Erin and Susan and they were great. I did not expect the amazing service we got from this place. It’s a definite must check out.
Tammy M — Google review
My wife and our friends came here on whim today. I don’t know a lot about wine but I know good service. From the moment we arrived, the entire staff was so helpful, friendly and accommodating. I didn’t catch all their names but Carolyn and Marcus, in particular, were phenomenal. They took the time to welcome us and talked with us for a while, not only about the wine. Bonus points for Marcus for tipping me off to a local bourbon drop. I had the Cupola white wine. Crisp, refreshing, and very tasty! At the end our visit we got speak with the Assistant wine maker, Rebecca, who was also a delight! Very sweet and knowledgeable. Her passion for wine was as bright as the Cupola.
WG J — Google review
We did the “cave tasting” and were served by Mark. He was fantastic! He knew a lot about the wines, the history of the winery/estate, and the area. He was very nice and understanding when there was some confusion about our payment. Boxwood was super accommodating with our request for a vegetarian charcuterie board. The cave tasting was a very intimate experience and mark kindly lowered the volume of the music for us. He explained each wine well and gave us some space to chat between each wine. Highly recommend this experience. Thank you Mark!
Shreya V — Google review
4.5 star. Came here (walked in with no reservation) with 6 other people, tried a few wines and ended with up 2 bottles. The wine was excellent. Only reason not giving a 5 star is because seating is limited indoor, they charge for water, and the music outside was so loud. I will definitely be back. Their club membership looks like a great deal!
T B — Google review
Each fall/spring, a big group of gals goes on a winery tour. This was our first time at Boxwood and we had a fabulous time. It’s some of the best Virginia wine we’ve ever had. A great outdoor atmosphere, beautiful space and setting. Plenty of room for groups, good food, and excellent service. We plan to return for our next tour!
Kristen O — Google review
We just love Boxwood Winery. It’s like a big family. Great wines, lovely facilities and good food.
Lew S — Google review
2042 Burrland Ln, Middleburg, VA 20117, USA•https://boxwoodwinery.com/•(540) 687-8778•Tips and more reviews for Boxwood Estate Winery
4 min · 1.3 mi
4

Scruffys Ice Cream Parlor

4.5
(98)
•
4.4
(34)
Permanently Closed
Ice cream shop
Scruffys Ice Cream Parlor, located on Middleburg's lively West Washington Street, has been a beloved spot for locals and visitors alike for three decades. The parlor is easily recognizable by its iconic ice cream cone sign and offers an array of treats including scoops, malts, shakes, and delectable ice cream sandwiches like the homemade chocolate chip cookie sandwich.
I loved the different flavor options here. Order at the window and in a few minutes enjoy your delicious frozen dessert. They offer waffle cones that they place in a paper tray with a wooden spoon. This makes managing your ice cream easier as there is no seating. People gathered in the alley or sat on stairs of the adjacent buildings. The ice cream is wonderful on a hot day and the kids will enjoy the treat. The decor is whimsical and this curios gem is worth seeking out if you’re in downtown Middleburg.
Preston B — Google review
Scruffy's Ice Cream Parlor in Middleburg has a charming country vibe and great ice cream. The White House Cherry is delicious. Don't miss the cute thrift shop next door!
Whitney B — Google review
Best ice cream in Middleburg! Plus they also support animal welfare organizations. Ice cream with a conscience! Can't beat that.
Steve H — Google review
Great ice-cream place in the middle of picturesque town of Middleburg, Virginia. Sometimes there are so many customers in line that patience is needed but well worth it!
Jan H — Google review
Very friendly and helpful. Cappuccino crunch and waffle cone and double Machiato were delightful.
Holly A — Google review
I'm a HUGE sweets and ice cream person, and this is by far the BEST ice cream I've ever had! The flavor immediately shows that the ingredients are very high quality and fresh, and the selection of flavors large enough for every preference. It'll definitely be a certain stop everytime I'm in the area. Every single local that saw us enjoying the ice cream mention, "it's good, right?" and with very good reason! You have to try it as well!
Diana P — Google review
We were in the mood for ice cream and decided to stop at Scruffys. What a great choice. Such a great selection. The ice cream was amongst the best we ever had. Sorry...no pictures of the ice cream because we forgot to stop eating it long enough to get a photo. #BirdLife #OwlsTweet #NomNomNom #IScreamUScream @MeetMrOwl
Erin ( — Google review
Such a great spot in Middleburg to get some great ice cream. I got Midnight Caramel River and I 100% recommend it! So amazing and creamy. Great place and friendly service!
Sarah B — Google review
6 W Washington St, Middleburg, VA 20117, USA•https://www.facebook.com/profile.php?id=61575121089564•Tips and more reviews for Scruffys Ice Cream Parlor
1 min · 300 ft
5

Fields of Athenry Farm Shop & Side Saddle Bistro

4.4
(118)
•
4.0
(44)
Butcher shop
Bistro
Farm
Farm shop
Meat products store
Fields of Athenry Farm Shop & Side Saddle Bistro is a charming family-owned establishment in Middleburg, VA. The cafe offers delightful breakfast options like the famous gluten-free FOA Waffles topped with fresh organic berries and powdered sugar. The warm hospitality of the owner makes for a memorable dining experience, as they go above and beyond to accommodate guests, even providing entertainment for children with chalk drawing on the floor.
We get our fresh turkey from this shop every year for Thanksgiving and have never had a complaint. Picked up some smoked bones at a great price for our dogs this year and they spent hours working on them. Thankful we live so close as it allows us to be returning customers.
Erin L — Google review
Popped in here for a drink while waiting for a table elsewhere. The bartender was nice and engaging. Told us about the place and the owners. Drinks were good but nothing to rave about. Their bourbon selection is good. Wish they had some bar snacks or something to munch on while drinking. The owners allow service men and women to sign the ceiling with their rank, name and unit. Pretty cool to walk around reading all the messages from those that served this great nation. It’s worth it to stop in and see the ceiling if for nothing else.
Mitch A — Google review
The butcher shop had no prices displayed anywhere. If you want to know how much something costs, you must bring it to the cashier who can then tell you. That's not a proper way to do business.
Philippe — Google review
I purchased meat from them for almost 5 years and have had problems on a few occassions. There normal answer is the customer is always wrong and they expect you to pay for their mistakes. In that time the quality of the meat has definitely gone down. On a few occassions I received meat which was freezer-burned and once received a bunch of inedible rotten hamburger meat. The most recent experience was the last straw. Bernadette ripped me off for over $300 because she shipped the order contrary to our written agreement which had been in place for the previous few orders. Her mistake, but she refused to give me a refund. Instead claiming some unwritten policy which she had made up in her head and it was my fault she didn't bother to contact me. That should tell you exactly what type of people you're dealing with there.
Kirk C — Google review
11 Thanksgiving turkeys with Fields of Athenry and so much more!!! Best ground beef, chicken, flank steak, osso bucco, hanger steak I’ve ever had! Amazing farm and family!
Jerry H — Google review
I have been ordering Fields of Athenry food for around 15 years. I use to have to drive a lot to pick it up but they now have a delivery truck which is so convenient. The quality of the food is excellent. It is healthy and tasty and we enjoy every meal I prepare with it. Thank you to the entire farm team for providing us with such a quality product:)
Valerie C — Google review
My husband and I absolutely love Side Saddle Bistro and the Fields of Athenry meats. Elaine and Bernadette are very kind and accommodating. The shop is a bit far for us to visit consistently as we live on the other side of the county, but luckily for us, we are able to order meats and cheeses galore online which is delivered right to our door every week! We always try to travel to the bistro when they host events and we always leave with big smiles and full bellies. You can taste the different in their meats compared to store-bought and I love supporting a local family business. We recommend Side Saddle to anyone and everyone.
Erin H — Google review
We love fields of Athenry! We can always count on their amazing farm fresh poultry and frequently use their Tex-mex sausages on barbecue nights. Their prepared meals are a lifesaver on busy days (the turkey pot pie being my particular favorite). And the drivers who deliver our food are always so friendly and accommodating!
Lucy E — Google review
7 W Washington St, Middleburg, VA 20117, USA•http://www.fieldsofathenryfarm.com/•(703) 300-5765•Tips and more reviews for Fields of Athenry Farm Shop & Side Saddle Bistro
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Where to eat

When you need a food break from visiting all the attractions today, these fan favorite restaurants are about a 15-minute drive away from Lost Barrel Brewing.

The Conservatory at Goodstone Inn

4.6
(40)
•
4.4
(325)
Restaurant
The food and service at The Restaurant at Goodstone were excellent as always. I enjoyed the lobster pasta while my companion had the mushroom risotto, both of which were flawlessly cooked and beautifully presented. One standout aspect of this establishment is their exceptional bread, something I don't typically indulge in at other restaurants but always do here without disappointment. The amuse bouche featured a delectable cheesy biscuit, and their desserts are truly exceptional.
We had an epic dinning experience the food was amazing my favorite course was the lobster and sorbet what a pairing the wine with each course was phenomenal as well. The vegetables are picked from there garden on site. I highly recommend Chef Paul is top notch!
Joshua L — Google review
Since we were staying at the Salamander Resort we wanted to check this place out for dinner. I was really impressed with the ambiance and the drive up to this Inn was nice. The food was on the expensive side for the portions you received but it was worth it. The bread that they have delivered here was some of the best I have had. I believe it comes from DC. We started off sharing a winter salad and the octopus. The salad was meh, I wouldn’t recommend it. The octopus was very good and the habanero sauce that came with it was a great addition. The chef sent a complimentary amuse bouche that was corn bread topped with caviar and some creme. It was delightful. I wish I had more of that! For the entree, I got the Guinea Hen and my wife got the Lobster Pasta infused with squid ink. Both of these dishes were wonderful and we didn’t leave anything on our plates. Finally we finished with the Affogato which was tasty but nothing spectacular. The service here was good. They take a team approach so we had a lot of people serve us, even the sommelier. I’d definitely come back if I am ever in this part of town again.
Kevin L — Google review
We had the most beautiful and delicious five course Christmas Eve dinner here. Incredible food. Great service. Beautiful atmosphere. We look forward to coming back more for special occasions in the future 🥰
Elizabeth F — Google review
The meal started off well enough. The oxtail amuse was good and the bread was fresh. The beet salad was delightful. The butter poached Maine lobster appetizer was in fact 90% salmon. Salmon is not mentioned on the menu. Beware of that. I knew I was eating salmon...I just thought maybe my friend was eating lobster. A duo maybe? Nope. I didn't realize until we were on our way back to the hotel that the couple we hitched a ride with through our car service complained about this and the server brought them some lobster from the kitchen. Interesting. I guess you have to realize you are being tricked to get what you pay for here. My friend ordered the Rockfish and it was very fishy. She ate around it mostly, eating the puree, which was delicious. I ordered the A5 Wagyu. It's $60 for 2 oz with a 4 oz minimum. Weird pricing arrangement on the menu. Just say it's $120 and that you can add more. I paid $180 for a bland sad steak with a Bordelaise that was reminiscent of a teriyaki for some reason. I didn't even finish it. It was just dull. It was accompanied with four thinly sliced Lincoln log stacked fingerling potatoes and a salad. The salad was probably the best thing on the plate. But I would argue, that it shouldn't be part of the dinner. It felt redundant. We had a salad as an appetizer. These prices were outrageous for what they were serving. The wine list was a little shocking. Not a lot of options for wines by the glass and bottles were very expensive. Maybe some more ranges per price points. It was all over the place. I understand the clientele they're serving but maybe come down a notch. New York City wouldn't even. The ambiance was nice and the drinks were good but I would not return. Service was okay but in my opinion, too many people touching the table can make for a confusing experience that doesn't feel very personal. It was however a very beautiful place with wonderful ambience.
Valerie H — Google review
Goodstone lived up to its reputation as a both a wonderful culinary experience with exceptional service. Our sommelier walked us through the thoughtful wine pairings, enhancing our experience by picking up flavor cues. Each dish of the chef's tasting was artfully plated. We look forward to our next evening at Goodstone.
Amante L — Google review
about a 40 person restaurant at the inn, we checked it out after being mentioned in Forbes magazine without much detail. the night we went thru may have been understaffed at the kitchen as our food took close to 50 min to arrive but at least they had some bread . overall the food was interesting and if your in to game meat this may be the place. our main dish took around 2:40 min to arrive.
Joe K — Google review
Dinner at the Conservatory was absolutely divine. The chef was very accommodating of a special request we had, and the food was stunning. It was only surpassed by the excellent service we received. We were guests at the Inn but even if staying elsewhere in the area, the restaurant is worth a visit!
Leslie — Google review
The restaurant is set is a beautiful setting that is true and our waiter was superb. The food not so much and for the prices you pay definitely not worth it. The dinner portion for the rock fish was a quarter of the fish filet or a 3” square for $42. Not even half of the fish. The beef portion was two little strips for $65 with nothing but some garnish. When they say fingerling potatoes they mean one slice of a fingerling potato. So not much in sides come with entree. You will not be filled with your entry and we don’t eat much. The highly anticipated poached pear missed the spot being underdone and the “vanilla” ice cream tasted medecine like. The idea of this restaurant is to keep buying food. We liked the setting but don’t feel the need to spend uber dollars to feel important.
Geo — Google review
36205 Snake Hill Rd, Middleburg, VA 20117, USA•https://www.goodstone.com/conservatory•(540) 687-3333•Tips and more reviews for The Conservatory at Goodstone Inn
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Day 5

Keep it simple
For day 5, these 7 places should be enough to fill your day with something exciting to do in Middleburg. Start the day with Cana Vineyards and Winery of Middleburg and make your way through the city to get to Middleburg Community Center. This should take about 8 hours of your day.
1

Cana Vineyards and Winery of Middleburg

4.4
(313)
•
3.5
(108)
$$$$affordable
Winery
Food & Drink
Vineyard
Wineries & Vineyards
Cana Vineyards and Winery of Middleburg is a must-visit destination for wine enthusiasts seeking not only fine vintages but also breathtaking views. The winery offers a warm and welcoming atmosphere, complemented by exceptional wines that will surely captivate your palate. With Melanie Natoli at the helm of winemaking, Cana Vineyards boasts an impressive lineup of nine reds, four whites, and a unique blueberry-apple wine.
I had the pleasure of photographing a wedding at Cana Vineyards and Winery of Middleburg, and it was a truly beautiful experience. The venue offers breathtaking views of the Virginia countryside, with rolling hills, vibrant vineyards, and perfect natural light that makes every photo stunning. The ceremony site is surrounded by the natural beauty of the vineyard, with lush greenery, open skies, and scenic vistas that create a stunning backdrop all on their own. The staff was incredibly accommodating and professional, helping the day run smoothly from start to finish. As a wedding photographer, I greatly appreciated the thoughtful layout and flow of the venue. It allowed me to capture everything from intimate moments to sweeping landscape shots. Cana is a dream location for couples who want rustic elegance and unforgettable scenery. Highly recommended! IG @jaysfineartphotography
Jason P — Google review
Beautiful winery with plenty of indoor & outdoor seating, wine options, and food options. We were bummed that although they have many outdoor fireplaces none of them could be lit due to it being too windy. The wine itself was mediocre—not the best but for the price, decent. Staff were very kind & welcoming. Very dog friendly—they even have a stand with dog treats and water bowls. Will definitely be back!
Tim B — Google review
A true hidden gem! The staff are warm and welcoming, which makes the experience even better. Loved that you can build your own charcuterie boxes such a fun and tasty option. Definitely recommend trying the Rosé of Merlot, it pairs beautifully.
Christy H — Google review
Beautiful scenery. Nice wines. Great staff. Perfect afternoon sipping on wine and relaxing on the deck.
John F — Google review
A very pleasant first visit. Also, the first all-Virginia wine tasting we've had where we enjoyed EVERY wine on offer. Very active location with plenty of seating and varied food on offer. Attractive setting and a generous wine club to join. We will certainly be back.
Derek R — Google review
My wife and I returned after several months and were immediately taken with the beautiful facilities. The views of the vineyards and mountains are great. The new Black Oak Cafe is fantastic and the pizza we had was delicious. We met the owner, Lisa, there and she was very welcoming. After sitting down with a tasting flight another employee (Don) met us to discuss the wine club. He has a wealth of knowledge and talked to us at length about their winemaking process. This is one of the best wineries we’ve visited in many years.
Steve G — Google review
Oh my goodness, the vineyard is absolutely gorgeous!! The wine slushies were amazingggggg and if you go, you have to stop by the cafe. It was adorable and so well decorated! Would highly recommend!
Hannah Z — Google review
We went for the first time and they were closing early due to a private event/wedding. Even though we were there an hour before this closing everyone was so preoccupied with prepping for the wedding they seemed frustrated to have to stop to get us two glasses of wine. Then they went around giving everyone a 25 min warning ro leave. There are plenty of other wineries we will go to next time.
Christy N — Google review
38600 Little River Tpke, Middleburg, VA 20117, USA•https://www.canavineyards.com/•(703) 348-2458•Tips and more reviews for Cana Vineyards and Winery of Middleburg
8 min · 1.8 mi
2

Chrysalis Vineyards at The Ag District

4.0
(275)
•
4.0
(193)
Winery
Food & Drink
Vineyard
Wineries & Vineyards
Nestled in the heart of the Ag District, Chrysalis Vineyards is a must-visit destination for wine enthusiasts and food lovers alike. Just a short drive from Salamander, this vineyard is renowned for being the largest producer of Norton grapes in the world. Under the guidance of owner Jennifer McCloud, who has made significant strides in Virginia's winemaking scene, visitors can indulge in an impressive selection of award-winning dry red wines crafted from native Virginia grapes like Norton and Petit Manseng.
I’ve been going to Chrysalis Vineyards since 2019, and it’s one of my favorite places to visit with friends! Their wine is fantastic, and the views and location are absolutely beautiful. The pizza is a must-try, too! I really appreciate that the upper level is reserved for adults only – it makes for a nice, relaxed atmosphere. Can’t recommend this place enough for anyone looking for great wine, food, and scenery!
Ili T — Google review
Went on a weekday! Great selection of wines and they also have a tasting menu. Pizza is delicious and also the cheese choices
Garima G — Google review
Pretty disappointed, we called weeks ago to ask if they sell Norton grapevines and the lady on the phone said yes, for Mother’s Day we should have them ready. We drove over and hour to get there to being told you don’t sell it. Oh well, the wine is good, but overpriced and the food is standard nothing special.
Tina M — Google review
We spent a wonderful Wednesday afternoon at Chrysalis Vineyards. The hot Italian pizza and a bottle of the Viognier is what we highly recommend. And I can’t forget the homemade cheese, it was FANTASTIC! (cheddar and the manchego were the cheeses of choice this trip). The scenery was beautiful and the weather made it even better. Big thanks to Debbie and Brittany for being such gracious, kind and knowledgeable hosts!! We will definitely be back in the future!
Erinn S — Google review
Love their wide selection of wines. This is our second time here. Food is excellent. Particularly the NY style pizzas. Norton Bull Run Mountain Cuvée is fantastic. We both enjoyed it so much.
John F — Google review
We reached there on July 5th 4pm and they were out of all Pizzas 🍕, they took the order and told us later, but thwy were nice enough to refund us the money back and we went to another winery 🍷 where we enjoyed our evening. So be careful they can run out of food without notice.
Priya.kapurnest P — Google review
The winery is very and peaceful, however you can’t see any vineyards from the main building and outdoor dining areas. Unfortunately the paninis we had were a bit dry and there were no condiments available to moisten them up. The wine prices are lower compared with other larger vineyards in the area. Glasses of wine start at $8 and bottles start at $20
Holistic G — Google review
This particular winery is famous for its Norton wines. I did a flight at the tasting and did not like any of them. My wife did a white flight and found then just okay. But it is not the wine itself that causes the low review, because I know wine is a personal taste. The entire experience was just not very well executed at all. No one there for our lunch and tasting seemed to know much at all about what they were doing. We stopped for lunch and it was okay, but haphazard on their part. You can do a flight with lunch, but not a tasting we were told. I can see that in a crowd that they don’t want food mixed with the tasting, but our group of 6 were the only people in the entire place from beginning to end. Because we wanted to sit, we got a server, not anyone who knew much of the wine. Overall, it was just not a good experience. We purchased nothing, which is rare for us at a winery.
Ralph B — Google review
39025 Little River Tpke, Middleburg, VA 20117, USA•http://www.chrysaliswine.com/•(540) 687-8222•Tips and more reviews for Chrysalis Vineyards at The Ag District
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Travelers
2
Rooms and guests
Rooms
1
Adults
2
Children
0
Travelers
2
8 min · 1.3 mi
3

50 West Vineyards

4.5
(207)
•
4.5
(67)
Winery
Food & Drink
Wineries & Vineyards
I love this winery! This was my first time here and breath was taken away by the incredible views. I was lucky enough to get a tasting by Olivia who was so nice and knowledgeable of all the wine, and she made our time here that much more fun! The wine was refreshing and very tasty! I’m not a big white wine drinker but I ended up getting a bottle of one of their whites because it was that good! You won’t be disappointed coming here, it’s relaxing, beautiful and stunning!
Laura P — Google review
Classy Vineyard with the Best Talent! Melanie delivered our wine tasting and, as devoted & well versed winery/VA Vineyard explorers, was easily one of the most knowledgeable and personable attendants we’ve yet encountered in our explorations. The food was very good and complemented the Governors Cup Winning (and Placed) wines well. The preforming acoustic guitarist played the perfect set for the sunny day. There are many great or fun wineries / vineyards in the area, but our experience today cements 50West as the must visit.
Sophia N — Google review
Exceptional. 50 West management knows what they're doing and it shows. The wines are mixed well and the staff know their product. Doug conducted my tasting after a bit of a operational sanfu and he did not disappoint. He offered rich history on the winery as well as knowledge on each wine and grape verietal. Speaking of wine, their guided tasting did not disappoint. You start off clean and fresh with a Viognier and end with a sumptuous red they've named Ashby Gap. The property itself is stunning sitting atop a hill that overlooks Bull Run. There are views upon views. And they are not done making it a full experience with the introduction of a cigar parlor and a Bubbly tasting room. 50W is here to delight you with an experience, not just a tasting
April C — Google review
We visited over a long weekend, arriving nearly an hour before closing, but the hostess warmly welcomed us and ensured we had a great experience. We were able to do a tasting and especially enjoyed the Chardonnay and Vidal Blanc. The rosé was also nice—its style leaned more toward an orange wine, which made it unique. The highlight, though, is the view—absolutely stunning. The winery offers a beautiful seating area where you can relax and take it all in. We’re already planning to return with a group and will definitely post an update after that visit. Overall, it’s a beautiful winery with excellent staff, delicious wines, and breathtaking views. Definitely worth checking out!
Sridevi B — Google review
Honestly, it is the best Virginia wine that I have had of the several Virginia vineyards that I have been to. Their Cuvée is excellent, as well as their Cabernet Franc and their Rose. Really well done wines! On top of that, the property and tasting room is beautiful and their staff is top notch! They make sure you are comfortable and have everything you need to enjoy your visit! Shout out to Gunner, who was informative, interesting to learn from and a great staff member! The tables on the patio are shaded, making for a beautiful afternoon spot to relax and enjoy the views of the mountains. This was the best experience I have had at a Virginia vineyard, let alone really any of the others I have been to (including in California, Maryland and Quebec)! Well done, 50 West!
Noah F — Google review
As a long-time wine enthusiast and someone who’s studied the art and science behind a great pour, I have to say: 50 West Winery absolutely delivers. I recently had the pleasure of visiting and was blown away not just by the wines—especially the Gunner, which is a standout blend full of depth and structure—but by the people behind the experience. Mike was incredibly knowledgeable and passionate, and it was clear he loves sharing what makes Virginia wine special. And Katie, the owner, brings such warmth and vision to the place—you feel it in every sip and every interaction. The setting is serene, the hospitality is top-notch, and the wine is made with true craftsmanship. Whether you’re a casual taster or a fellow wine nerd like me, this place is worth the trip. Cheers to more bottles of Gunner and good conversation!
Brenda D — Google review
50 West Vinyards owner Katie and the staff went above and beyond to make our wedding event just PERFECT! Katie made sure all our questions were answered and requests were met from the planning stage to the day of the event. Their fully-renovated tasting room has gorgeous deck overlooking vineyards, giving us so many great photo opportunities. It was also convenient that we were able to rent out a room in the house for the bride and wedding parties to be ready. The staff who attended the bar was super friendly and knowledgeable. Katie and the staff were so accommodating, professional and supportive. All of our guests made so many positive comments about everything they experienced - the venue, the service, and the wine!! We highly recommend 50 West Vineyards for not only events but also one afternoon visit to relax and enjoy their wine!!
KM P — Google review
I had 2 of their red wines and they were both very smooth. My wife also had 2 white wines and they too were great. Highly recommend this place. Very nice scenery too. Very peaceful and lovely views
Muscle E — Google review
39060 Little River Tpke, Middleburg, VA 20117, USA•http://www.50westvineyards.com/•(571) 367-4760•Tips and more reviews for 50 West Vineyards
10 min · 4.9 mi
4

The Christmas Sleigh

4.5
(62)
Christmas store
Nestled in the heart of the United States, The Christmas Sleigh Inc. is a delightful European-inspired shop that captures the essence of holiday spirit all year long. This enchanting store boasts an impressive collection of traditional German and Austrian ornaments, nutcrackers, music boxes, and unique decor items that are sure to bring joy to anyone's festive celebrations.
I love this store! They have beautiful ornaments and many from Europe. It’s like going to a Christmas market in Zurich! There are many expensive things but I always find something reasonably priced to buy!
Nikki F — Google review
A gorgeous little German store with authentic Christmas decorations, cloths and artifacts. Such a fun shop to visit. Definitely on the expensive side of the price bracket however the quality of the decorations is 100% autnentic! Worth the trip! Plus, Middleburg is such a beautiful little town full of elegant boutiques and little restaurants.
Cristina T — Google review
So so cute. Staff was very friendly and helpful. Great selection of Christmas items, many of which were handcrafted. They even had some gourmet food items and clothing!
Lily — Google review
Such a cute, unique shop! A little pricey IMO, maybe offer a daily deal when people come in the store. Definitely worth a visit to check it out. Would not recommend little kids to go inside. Friendly staff.
Hayley M — Google review
I am sure the store is great in person, but if they are going to have an online presence, they need to up their game. More staff (who do not sound overwhelmed and harried on the phone) leading up to Christmas, and a website that doesn't let you place orders on out of stock items would be a start. This is especially true for a store that sells nothing but Christmas-related products! I placed an order 11 days ago, never received a receipt for the initial order, and have yet to see a refund for two items not in stock or an updated receipt for the changed order. The good news is that the order has been shipped but I still don't know the total of my revised order! I love brick and mortar stores and I wish them the best, as I'm sure it is great to shop there ! I wish I could.
Abwald — Google review
If you can't make it to Germany at Christmastime to visit the markets, then take a trip to historic Middleburg, Virginia! This shop reminded us of our 2017 Germany Christmas market tour. Filled to the rim with beautiful European trinkets, clothing, ornaments, Byers dolls and more, I dare you to walk out without buying something!
Diane R — Google review
I discovered this shop on-line and was really impressed with the quantity of items they had. My husband was born in Munich and he is getting more Bavarian with every passing year so we enjoy having German decorations for the holidays. It is difficult to find them in the US and a lot of places only carry a very limited selection. I was pleasantly surprised by this store- it even carries some things I had only seen for sale in Germany. The prices are not cheap but quality German hand-made items are not cheap even in Germany. The order arrived today and was beautifully packed. I am already planning what to order for Christmas...
Guenther T — Google review
Absolute best store for authentic German items. Prices are a little more than others but Dieter runs a great small business and it's the kind of place you'll want to come back to for years
Matthew H — Google review
5 E Washington St, Middleburg, VA 20117, USA•https://www.thechristmassleigh.com/•(540) 687-3665•Tips and more reviews for The Christmas Sleigh
1 min · 300 ft
5

Knead Wine

4.7
(89)
•
5.0
(2)
$$$$very expensive
Wine store
Takeout Restaurant
Pizza Takeout
If you find yourself in Middleburg, make sure to stop by Knead Wine, a charming establishment that beautifully marries the worlds of fine wine and gourmet pizza. This boutique wine shop offers an impressive selection of local, regional, and international wines paired with delicious artisanal pizzas like truffle and basil. The inviting atmosphere is perfect for unwinding with friends or enjoying a leisurely afternoon.
After hearing so many positive things about Knead Wine’s pizza and overall concept we had been wanting to try it out, but since they don’t have a dining room, it’s really tough since we live an hour away and we’d rather eat fresh, hot pizza than to take it to go. So, recently when we were in the area to visit a winery that permitted outside food, we stopped in her first and got a couple of pies… The two pizzas we ordered were phenomenal! The dough was outrageously excellent and perfect! The texture, density, and definitely the slight char on the crust. The toppings were of high quality and each of the pizzas came together to be very tasty and amazing! We will most definitely return if in the area with the same opportunity to take it and still eat it while it’s fresh and hot. Just wish they had a dining room… also they need to offer plastic utensils to take away to use. Highly recommend stopping in here!!
F'burg F — Google review
We just stumbled upon this place while driving south. Their pizzas are absolutely phenomenal. This is take-out only so we were slightly disappointed that our seating options were limited to outdoors. That wasn’t a big deal for us, the pizza was still absolutely delicious. Great wine options available! Did not expect them to sell freshly made cookies, this was hands down the best cookie I’ve ever had. I’m actually kind of glad that this location is a bit far from us because I would have been a weekly customer, haha. Great customer service, welcomed by a cute dog!
Ximena D — Google review
Recommend the SVR! Great people, great energy. Pizza has high quality ingredients, smart flavor combinations. Crust gets a little chewy if not eaten almost immediately in case your used to the big chain style crusts but thats how hand tossed dough works.
Matt C — Google review
One of the best pizzas I’ve ever had (and I’m admittedly a pizza snob after growing up outside NYC and living in Italy for a few months). I got the trucks pizza and the flavors were just perfect together, and the crust was a delicious Neapolitan style thin crust. Would go out of my way to go here again.
Kirstyn R — Google review
Such a cute little shop. The pizza smelled so good that we had to try it and let me tell you, it didn’t disappoint! Such a great menu of choices too. We ended up getting the Waters pizza. The shop staff were super friendly as well. It was VERY clean inside. Fair prices on the wine with great selection including local wines too. Highly recommended stopping in if you’re in town!
Jayme C — Google review
Popped in last nite to pick up 2 bottles of wine, which are both excellent! Great service. Great wine. Looking forward to their pizza next.
Harry G — Google review
Found this spot when searching for lunch spots passing through Middleburg. It did not disappoint. We had the Rhodes and the Trucks. Both were excellent. We are pretty particular about our pizza being from the Northeast. Also really enjoyed the chocolate chip and peanut cookies. We were pleased with the recommendations on wine as well. Grabbed three bottles we’d never heard of based on the recs and enjoyed all of them. Appreciated the selection and the pricing simplicity.
Kathryn P — Google review
Amazing wine spot. Owned by one of the only 4 level 4 sommelier in the world. Iconic. Very friendly staff with an adorable dog.
Michele — Google review
5 W Washington St, Middleburg, VA 20117, USA•http://www.kneadwine.com/•(540) 687-5150•Tips and more reviews for Knead Wine
1 min · 400 ft
6

Middleburg Antique Gallery

4.4
(59)
Antique store
Middleburg Antique Gallery, located on Washington Street, offers a wide selection of unique home pieces ranging from vintage to mid-century to modern. The antique furniture available caters to every taste with formal English, American, and European styles. In addition to furniture, the gallery also features jewelry, art, rugs, fishing & sporting antiques collections and more. Visitors can explore the surrounding area of downtown Middleburg and discover chic clothing stores and secondhand shops.
I am not one to visit antique galleries. But, I admit this is especially worthwhile. The product variety was extremely interesting. I purchased baccarat glasses, and the owner shipped them to me, and they were received without damage. I recommend this wonderful shop. The staff are exceptional.
Robert B — Google review
This antique gallery consistently offers a unique and thoughtfully curated selection. The staff is both helpful and well coordinated, making each visit enjoyable. I highly recommend stopping by and experiencing it for yourself.
Cuy M — Google review
Love this store. Beautiful things, and a horse girl treasure trove. Lisa was so sweet and helpful. I’ll be back!
Annie F — Google review
Very high quality. Herend ceramic figures, hermes scarf, gucci goods, high-end furnitures. They have the good stuff as well as more affordable trinckets. The place was much larger than I expected from the storefront, as the store is deep and over two floors. It had the best curated selection among the many stores I visited in this town.
Philippe — Google review
paid $80 for a pearl necklace that was not in good condition and broke the moment it was in the box. check the quality before buying stuff here. never even got to wear it.
Camy R — Google review
It looks like a museum. Pricey, but very beautiful antique store
A J — Google review
Beautiful and friendly antique store. Love all the amazing jewelry! Had a great experience talking to Lisa, she helped us pick out jewelry and purse for my daughter’s prom. Friendly service and unique vintage finds! Will go back again.
Gin B — Google review
When I visited I didn't know that the area was known for its hunting and equestrian heritage. It's very apparent in this store, with it's stuffed foxes, fox and equestrian art, etc. If you're looking for jewelry for a horse lover, this is the ideal place. The fox plates/dish sets I saw here were just adorable. The prices were higher that I expected, but it's probably about right for its locale. The store is larger than it seems from the outside, so it's definitely worth going in and taking a look.
Jennifer R — Google review
107 W Washington St, Middleburg, VA 20117, USA•http://middleburgantiquegallery.com/•(540) 687-8680•Tips and more reviews for Middleburg Antique Gallery
2 min · 0.11 mi
7

Middleburg Community Center

4.7
(52)
Event venue
Auditorium
Banquet hall
Community center
Middleburg Community Center is a fantastic destination for families and nature lovers. The well-maintained grounds offer a beautiful playground and ball field, making it an ideal spot for kids. Throughout the year, the center hosts various events such as art shows, gardening classes, concerts, pool parties, and barbecues. It's also a popular venue for weddings due to its historic charm.
It's an awesome school staffed by amazing set of teachers and Principal! We feel very lucky to have been part of this community and hope to continue for years to come
P S — Google review
Viewed alice in wonderland tea at the center. Great space for event. Wonderful old building. Not a lot of parking.
Elize H — Google review
Shame on you Mr. Nutter! I was there that day and the only thing that went wrong was YOUR WIFE's obnoxious behavior. The staff that day were friendly and helpful. Until your wife caused an ugly scene over a simple mistake made by you/her, everyone there was enjoying a nice afternoon at a great facility. No one even CARED until SHE lost her maturity and acted so ugly. And, YOU did nothing to calm the situation. She should be very grateful that when she tried to engage me in negative comments about the staff that I SHUT HER down so quickly, because I truly wanted to tell her off! But, I was not going to add to drama in front of my 9 year old stepdaughter who was just trying to have fun.
Angela J — Google review
Really nice place first time we have been.
Shawn F — Google review
Little small town with vibrant friendly people. Very nice and interesting place for a early morning or late afternoon troll. Finest dinings and hang out. Much better than old town Alexandria VA. 30 miles away from Tysons VA
Dara V — Google review
Fantastic small town Community Center! Beautiful and immaculately kept grounds. Great little playground and ball field right next to the local library is a great place to take the kids. My family loves attending all the events at MCC. Springtime we enjoy art shows, gardening classes, and the Concerts on the Steps. Summertime, Parties in the Park and swimming at the pool (with a great diving board! You do not see those anymore.). Fall would not be complete without Hot Dog it's Halloween, Community Thanksgiving Dinner and more Concerts on the Steps. Wintertime brings the Holiday Ball, a truly magical evening that is the perfect start to the holiday season.
Hastings F — Google review
Went to a wedding here and it was beautiful outside. The buildings are so historic that it makes you feel like your stepping back in time. If only!
Beth L — Google review
I have availed myself of the Middleburg Community Center is many ways , and can attest to its welcoming and innovative staff, especially Olivia Rogers, its accessibility, it's functionality, and its integral presence in the Middleburg area. Our communinty is elevated by its presence.
Gail W — Google review
300 W Washington St, Middleburg, VA 20117, USA•http://www.middleburgcommunitycenter.com/•(540) 687-6373•Tips and more reviews for Middleburg Community Center
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All road trips from Middleburg

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Explore nearby places

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  • National Harbor
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All related maps of Middleburg

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Middleburg throughout the year

  • Middleburg in January
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