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3-Day Lanesboro Itinerary

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Wanderlog staff
Updated
• updatedAug 20, 2025

Lanesboro in 3 days

If you only have 3 days to spend in Lanesboro, we’ve narrowed down the top places you should check out to get the best experience of your time here.
With favorites like Jiminy Peak, Pontoosuc Lake, and Greylock Grounds Coffee Drive-Thru & Cafe, 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 Biggins Diggins and Olde Forge Restaurant so you can get the best taste of Lanesboro 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 Lanesboro?
  • 1-Day Lanesboro Itinerary
  • 2-Day Lanesboro Itinerary
Visiting Lanesboro? See our Lanesboro 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
  • Lanesboro in 3 days
  • Most popular attractions
  • Northwest side of town
  • Proximity is everything

Day 1

Most popular attractions
For day 1, we strategically grouped the most popular attraction, Ashuwillticook Rail Trail, 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

Mount Greylock State Reservation Visitor Center

4.8
(812)
•
4.5
(344)
State park
Nature & Parks
Campground
Lodging
The Mount Greylock State Reservation Visitor Center in Massachusetts offers over 70 miles of trails, including 11.5 miles of the Appalachian Trail and is home to the highest point in the state. It's a popular spot for hikers with various trails to explore, while visitors can also drive up to the summit and admire the monument honoring war veterans. The area is particularly stunning during fall foliage, offering breathtaking views year-round.
This is not only the highest point in Massachusetts but also the best place to see fall colors. This reservation is very well kept and organized by the MA DCR, the visitors center has good maps, and great service. The trails are well marked and in good condition, as are most of the roads. I cannot think of a better place to visit with nature in the Berkshires.
Eduardo M — Google review
It's a great area and there are like several trails that branch off but you can follow markers. There are waterfalls and cascades through the trails. Flippin beautiful.
Celi K — Google review
Incredible Views. I always wanted to visit Berkshires and Mt. Greylock was the cherry on top. We drove up from the visitors center to the very top and climbed the tower. It was beyond amazing. I could sit up there for days just looking down at the town (I believe it's Adams) below. It felt like I was in a foreign land. I am from Eastern Massachusetts and I have been as far west as Greenfield but I've never ventured any further than that. We took the Mohawk Trail over to North Adams then stayed in Pittsfield. We left the next day and climbed the mountain. We stopped along the way to check out some of the views on the way up but nothing was like the view from the top. We climbed the tower which was amazing, then stayed and looked at the view for a little while longer before heading back home. I highly recommend taking the trip. To anyone, even people in the area it's a must see. If you're from Eastern MA like me, and have never seen it; or another state entirely, it's an experience you don't want to miss.
Andrew M — Google review
Sweeping views from the top by the tower. Many hiking trails of varying difficulty to choose from. Visitor Center staff are knowledgeable and provide up to date info on trail conditions. Bascom Lodge at the top has a limited menu of breakfast/lunch stuff, and also has great views.
Judi S — Google review
Superb views from top....3.4k ft height...car road up to top and many trails all around...about 2.5hrs for hike to top.
Pravin T — Google review
Beautiful trails. Great dcr guides downloadable with QR codes at the visitor center. Bradly Farm loop highly recommended
Mark F — Google review
We thoroughly enjoyed our trip to the Berkshires and Mount Greylock. The trees are starting to change colors. Visitor center is clean, staff is friendly and they have pamphlets, a movie and restrooms. The road is gradual and wide enough for two cars to pass each other. Also has good hiking pedestrian signs. It's safe, well gloomed and the wildflowers were beautiful. At the top is a beautiful tower monument honoring the heroes who protected this nation with a beacon on top. You can go inside and up the spiral staircase to the top. On a clear day you can see for 90 miles. Parking on top is nice with two stone lodges. The day we went the fogg was thick. You could barely aee the tower. Still it was fun! I have never seen that much fog and deeply moved by the monument. I highly recommend going there and to all the attractions in the area. I have been to Mount Greylock when ir wasn't foggy too. The view is wonderful. .
Norma P — Google review
Beautiful drive up and outstanding views from the top of the tower...4 sets of narrow stairs to climb, but worth it!
Kim A — Google review
30 Rockwell Rd, Lanesborough, MA 01237, USA•https://www.mass.gov/locations/mount-greylock-state-reservation•Tips and more reviews for Mount Greylock State Reservation Visitor Center
9 min · 2.5 mi
2

Bill Laston Memorial Fields

4.9
(36)
Park
The Bill Lasting Memorial Field in Pittsfield is a wonderful place to visit. It has easy access from Rt7 and offers ample parking. The snack stand provides a variety of high-quality goods for visitors. The bathroom facilities are well-maintained and the grounds are kept spotless. The baseball field itself is impressive, with a nice scoreboard and thoughtful design. Overall, it's a great little league park that clearly shows a lot of care and intention went into its creation.
Love the (new?) basketball court...along with the cute little playground, and walkway that wraps along the river. We went geocaching today;), but unfortunately we were unable to find the cache..? Aside from that, this area offers plenty of options for anyone who wants to play with a ball/ run around, or just enjoy a stroll along the river.
Meredith S — Google review
A very nice venue, so thoughtfully put together. Clearly a lot of care and intention was put into the design of the space.
Carla M — Google review
Great place to take the kids. Playground, ball fields, and a walking trail. There is a shallow cool brook around the park, perfect for hot summer days.
Heather M — Google review
Great baseball field, nice scoreboard, bathrooms were clean and we'll maintained. All and all a very nice little league park. Sorry no pics, I was too engaged watching my son in a very close game. 8 to 8 in the 6th!
Brian S — Google review
Was up from CT visiting friends in Pittsfield, when part of this visit ended up at Bill Lasting Memorial Field to see a BB game. Easy access from Rt7. Parking, nice snake stand with a variety of H/C goods. Bathroom and the grounds were spotless. Nice place. Bravo Zulu to the grounds keeper.
Dean S — Google review
Very nice sports complex, plenty of baseball,foodball fields and a nice walking track that goes around the whole place. They also have restrooms and a little play area for the young kids snd the whole place is very well maintained.
Joe B — Google review
Absolutely love what they did with the space. It's very clean and well maintained. I say the first because I remember what it was like after the old drive in closed. A great use of the space and tribute to a life lost.
Frank D — Google review
Well maintained park with lacrosse, football, softball, and baseball fields. Positioned next to beautiful Town Brook, complete with picnic table and grills.
Sean M — Google review
417 N Main St #409, Lanesborough, MA 01237, USA•(413) 442-1167•Tips and more reviews for Bill Laston Memorial Fields
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Travelers
2
Rooms and guests
Rooms
1
Adults
2
Children
0
Travelers
2
5 min · 2.1 mi
3

Lanesborough Country Inn

3.7
(108)
Motel
Inn
Nestled in the heart of the Berkshires, Lanesborough Country Inn offers a cozy retreat with basic rooms and private log cabins, some equipped with kitchenettes. The inn is conveniently located near Pontoosuc Lake and iconic attractions, making it an ideal base for exploring the area. Guests can enjoy amenities such as BBQ grills and free WiFi during their stay. The private cabins provide a spacious and quiet escape, perfect for those looking for a peaceful getaway.
We rented a cabin for the weekend and had a great stay. The cabin was cute, clean, and perfect for two people. The bed was comfy, the heat worked great, and we were set far back from the road so it was very quiet. The noisiest part was the three enormous pickup trucks and burly men the morning we left, but otherwise very peaceful.
Kate T — Google review
We stayed in a two queen bed cabin at the Lanesborough Country Inn. It's a good thing we called to say we would be in late because the clerk said the office would be closed so a key would be put under the rug on the porch. And when we left we just put the key in a box because the office didn't open until 9:30am! I'm glad we didn't need anything during our stay because we never saw a single person. The cabin room was big with very high ceilings. It was 60 degrees in the room when we got there and it took us 15 minutes to figure out how to make the temperature on the heater increase. We were freezing and there was nothing to tell us how to do it. The beds were comfortable and the blanket very warm, soft, and cozy. I didn't have a top sheet on my bed. Watching TV in bed was comfy, but the channels changed very slowly and there was no guide, so it took awhile to find what we wanted. The bathroom was small and the light too dim but had a whirlpool tub. The cabin also had a kitchenette which we didn't use. There was also a couch and big, old dresser. Once the cabin warmed up, we both slept really well! It was very quiet too. I guess we would recommend the cabin only because we slept so well and that was basically all we needed from the room.
Claudia P — Google review
It wasn't bad for the pricing. I would have liked it more if; A. Our bathroom door wasn't kicked in. And B. If the crawl space wasn't wide open. Our memorial day weekend was definitely memorial since we got food poisoning from one of the restaurants in Pittsfield.
Sarah N — Google review
Stayed in cabin #12. Funky smell, like cigarettes and cat urine. Cracked tile throughout "kitchenette" and bathroom, that the manager tried saying we damaged when we reported it! Don't be fooled by the term "kitchenette" as it's far from that. No stove. No oven. No dishwasher. Mini fridge only that will freeze everything you put into it, even at low setting. You get a dirty microwave with glass "turn" table that not only doesn't turn, but isn't even the correct fit. Ancient hotplate, chipped dinnerware, and rusty pans. Floors were gritty. AC smelled like it had been in a musty basement for ten years and the ceiling fan didn't work and had about an inch of dust on it. You won't get a hot shower for more than 5 minutes, as the hot water heater is about the size of a large thermos. Bed had a sinkhole on one side, come to find out it's some used sleep number bed that they don't tell you about, therefore you won't know there are are least 2 dirty boxes underneath the bed that won't be plugged in. Explained the 2 remotes we found, that the staff at front desk can't tell you anything about or how to use them. My back and ribs ached for days. The worst discovery....BEDBUGS. My son was bitten a couple times and that's when I realized we needed to inspect. We couldn't have left sooner and we will NEVER be back. Sketchy employees. Another guest mentioned one is a sex offender. I didn't see that listed on the website...
Krystal F — Google review
Do NOT book this motel. The room we were first given was unclean (horribly stained sheets, comforters and pillows) and smelled strongly of cigarettes (the rooms are clearly labeled as "smoke free"). Upon complaining to the woman working the front desk, she handed us an empty bottle of febreeze and said that there was "nothing else (she) could do" to help unless we were willing to pay an additional $100 or so to upgrade to a cabin. We decided to look into that option (the interior of the normal room was honestly so putrid that we were desperate enough to consider the last minute upgrade), only to find that the cabin was ALSO unclean and smelled strongly of cigarettes. We actually looked in two cabins - both were equally as awful as the room. In the cabins, the bed mattress was suspended by two tables instead of a frame, the kitchen appliances were too unkempt or dirty to actually use, and the front door was exremely worn with multiple holes in the wood large enough to look through. Needless to say the service was abysmal - the woman we spoke to was unenthusiastic and unwilling to tend to our concerns. Because we had nowhere else to go, we stuck it out in the disgusting cabin. I will say, the Dollar General next door is a nice touch - at least you can purchase some reasonably priced sheets to cover the bed and couch for the duration of your stay.
Joshua Q — Google review
A delightful cabin at an affordable cost. These cabins are very clean and comfortable. I like sleeping back away from the road where it is nice and quiet. The staff is very polite and helpful.
Paula S — Google review
We stayed in one of the private cabins for a long weekend. It was prettyspacious, allowed our dog, and the site is very convenient to Mt. Greylock, Pittsfield and surrounding towns. Cabins are part of a motel and its surroundings are commercial. If you can get past that, this is a central location offering private, quiet, and socially distant lodging.
Larry B — Google review
A wonderful experience the bed was soft and great the cabin was beautiful and the staff was friendly we definitely will go there again
Heather P — Google review
499 S Main St, Lanesborough, MA 01237, USA•(413) 442-1009•Tips and more reviews for Lanesborough Country Inn
9 min · 5.6 mi
4

Donnybrook Country Club

4.7
(73)
Permanently Closed
Golf course
Country club
Public golf course
Wedding venue
Donnybrook Country Club is a picturesque and challenging golf course located in the Capital District. The layout features diverse and rolling hills with stunning mountain views. Despite some challenges like blind tee shots and bunkers needing work, the fairways and greens are well-maintained, offering an enjoyable playing experience. The course is known for its reasonable pricing and accommodating staff, making it a hidden gem for both locals and visitors to the Berkshires area.
Great afternoon at Donnybrook CC. Played the course while vacationing in the area. The course and greens are in great shape and the surrounding scenery is beautiful.
Mike S — Google review
Very much enjoyed our round here. Fun course with a diverse and challenging layout. Gorgeous views and reasonable pricing, too. Fairways and greens in very good shape despite all the rain they’ve been getting. Bunkers need some work (which again might be because of all the rain), and with some of the blind tee shots they would be smart to put bells in some fairways to let the next group know you’re clear. All in all highly recommend. Fun place to play.
Brad Y — Google review
Very enjoyable day. Was by myself but was put with a member who made my time great!! Nice course with challenging greens. Good price too! Will happily return.
Bob L — Google review
I've played a lot of different courses in the Capital District and Donnybrook by far is the best manicured course I've played both this year and in past years. The fairways are pristine and so are the greens. Very reasonable pricing also. I highly recommend this course even if it's a bit of a drive from Albany.
Colleen D — Google review
Well maintained and picturesque golf course. However the pace of play here was so terrible that my group left midway through our round. Each tee box consisted of 2-3 groups waiting to tee off. It took 4 hours to get through 9 and was only getting worse as we saw more people being sent onto the course. I would not recommend unless you know it’s going to be a slow day.
Zachary C — Google review
Best Hidden Golf Gem in the Berkshires! Don’t pass up this 9 hole track. The course is fun & challenging. Plus, it has a nice deck to enjoy a beverage and watch other players play #9.
Bryan C — Google review
One of the true gems of the Berkshires...great finishing holes, amazing groundskeeping by the Kellys
Don W — Google review
Wonderful layout on rolling hills. Great views of the mountains. This course is not overbearingly hard. Yet it will challenge most golfers. The gentleman at the front desk was very accommodating!
MARK F — Google review
775 Williamstown Rd, Lanesborough, MA 01237, USA•http://donnybrookgolf.com/•(413) 499-7888•Tips and more reviews for Donnybrook Country Club
3 min · 1.3 mi
5

Ramblewild Adventure Park

4.9
(180)
•
5.0
(674)
High ropes course
Tours
Adventure sports center
Recreation center
Zipline & Aerial Adventure Parks
Ramblewild Adventure Park spans over 10 acres and offers a variety of thrilling activities such as high wires, zip lines, rope ladders, balancing logs, cargo nets, and suspended bridges. The park features family-friendly sections suitable for both children and adults. Visitors praise the beautiful location and friendly staff who go above and beyond to ensure a special experience. Guides are commended for their support in helping those with fears overcome challenges.
First time visiting from Maryland. This place is amazing. Courses for my 10/11 year olds and then a more challenging for the 20 year old. The staffing is super friendly and attentive. They watch over, but don’t get involved unless your struggle.. there to help for sure. If we ever make back up this way… definitely will do again!!!
Toni M — Google review
1. Safe 2. Fun 3. A great workout for the body and mind 4. Fresh, clean, air direct from trees no more than a few feet away 5. Nice, helpful, supportive, professional, caring staff (Thank you, Maddy, Dillon, Ian, and the rest of the team) 6. Special attention to ecological sustainability in their operations — they don’t talk about this unless you bring it up 7. Whether you stick to base camp, or take on hemlock’s revenge, it _will_ be a very uplifting and positive activity for the entire group
Kannan T — Google review
Our family loves Ramblewild. It was so much fun to bring our friends with us this last time. The best part is the individual attention and coaching we received from the staff, if we needed it, like I did :) And my kids were able to go ahead and move more quickly on the course with one guide while another guide stayed back with me at my pace. There are 8 long courses which are uniquely exciting & make my kids want to keep going back for more. Have been to a number of different ropes courses in NY & MA and Ramblewild is by far our favorite. Oh, and they make their own maple syrup which is delicious.
Chris J — Google review
This place is a ton of fun, that also provides a pretty good workout on the harder courses. The staff was great, and the scenery was beautiful. I would absolutely recommend to anyone.
Joshua G — Google review
Highly recommend Base Camp experience !! I had 2x 6 year olds and an 8 year old with me for the adventure. I wasn’t able to find many reviews for the Base Camp so we stopped before making the reservation. There was no one using it when we stopped so they let us take a quick peek and check it out. All the staff, especially our main guide, Maddie were awesome with the kids. She explained everything so they understood and was excited, energetic and patient when needed. We had 1 that was scared of the zip line at the end of the course, Maddie was so patient and after a few attempts and a return to the training ground, she helped her overcome her fear and then couldn’t stop her from doing it again!! All the kids were sad when it was time to leave. It was challenging and exciting for both the kids and I. Highly recommend and can’t wait to get back to do it again!
Erin C — Google review
Wow! What an experience! We had never done anything like this before and it was amazing. The gradual increase in difficulty coupled with a friendly guide made us feel so comfortable. Absolutely beautiful setup among the trees with lots of shade. Highly recommend!
Emily B — Google review
I had an amazing experience at Ramblewild Adventure Park. 4 hours is plenty of time to do the courses and even have a little picnic! The staff is very welcoming and supportive. They also give tips on how to go through an obstacle, if you need it. I definitely recommend to go there if you like activities!
Evelina W — Google review
We love Ramblewild and have been multiple times. Basecamp is great for ages 4-10 while the high ropes course is a blast for older kiddos and adults. The forest is magical and cool on a hot summer day. The staff are kind and knowledgeable. A must visit!
Elea K — Google review
110 Brodie Mountain Rd, Lanesborough, MA 01237, USA•https://newramble.com/•(413) 499-9914•Tips and more reviews for Ramblewild Adventure Park
9 min · 2.7 mi
6

Hendrick's Summit Lodge

4.3
(46)
Cafe
Hendrick's Summit Lodge in Lanesborough is a must-visit destination known for its exceptional food and services. The lodge offers a new menu featuring delicious artisan grilled cheese sandwiches, with the buffalo grilled cheese being a standout favorite for those who enjoy some heat. Visitors can also savor great chili and beer while enjoying the relaxed vibe away from the bustling spots at the bottom. The lodge provides stunning views of the mountain, making it an ideal place to unwind and take in the scenery.
Love the new menu. The artisan grilled cheese sandwiches are amazing. Especially the buffalo grilled cheese with the works… be careful, it’s spicy! The chili is great and the beer. The vibe is much more relaxed compared to the busy spots at the bottom
Kathy L — Google review
Closed, so can't tell you about the inside. But after a hike up the main slope it was a nice place to sit and relax and eat my own food. The view is great.
Tom K — Google review
Nice to have a place to stop at the top. Crowded but good. Food is reasonable for a resort.
Mike C — Google review
They have a lot of undisplayed prices on their menu, which I believe is ilegal according to Massachusetts law. Julie
Catherine T — Google review
Had the mountain all to myself. Didnt even need the chairlift with my turbo levo. Also quite the view. Would love to see the lodge open back up!
Mikefoley89 — Google review
Great place to come in out of the cold at the top of the mountain. Excellent tomato basil soup. Thick and hardy
Frank Z — Google review
Basic eats hot and cold including salads and yogurt. Yummy cinnamon buns and hot chocolate. Beautiful view.
Debra F — Google review
The food is just okay and there are not a lot of options beacuse the size of the place but it's a really cool experience eating at the top of the mountain and seeing the view
John T — Google review
Lanesborough, MA 01237, USA•http://jiminypeak.com/The-Mountain/Shopping-Dining/Dining•Tips and more reviews for Hendrick's Summit Lodge
< 1 min · 0 ft
7

Jiminy Peak

3.9
(56)
Mountain peak
Jiminy Peak in Hancock, MA, is a popular destination for skiing and outdoor activities. The mountain offers a variety of trails suitable for skiers of all levels, making it a great option for families. Visitors can enjoy the convenience of the Country Store, which serves as a general store, coffee house, and post office. The lodge provides comfortable amenities such as cushioned chairs and delicious food options.
Great for hiking, follow the lift going up for a challenge or follow the service road for an easier route. Bring water, bug spray, camera and something to eat.
Tom K — Google review
This place is amazing I am going next year
Lyvia L — Google review
We had an excellent time! My friends and I drove up from Westchester on a Friday morning and were able to hop right on the mountain. The lodge was sweet; food was great and reasonably priced. Rentals were quick and easy. Definitely a dignified experience. I will definitely be coming back in the future!
Z — Google review
Best skiing in Massachussets. If you are looking to travel a short distance and maybe spend a day at any mountain near you, let it be Jiminy. The trail variety is great and there are great options for skiers of all skill levels. Difinitely kid friendly And the lodge is great since it had chairs with cushions which is a big plus. Food is overpriced, but that's what you expect. Pro tip, I forgot my goggles and so instead of buying a new pair for like $70 I just went to lost and found and they let me borrow so shout out to those people.
Dillon M — Google review
Honestly, the mountain was fine, but this score is due to the scammy nature of the services offered. For exmaple, I paid for private training and the instructor didn’t give any instruction just encouragement. Totally ridiculous. I derived NO value whatsoever from my private lesson. 100% never coming back
Omar A — Google review
Nice mountain for family skiing. Everyone was very helpful.
Carolyne D — Google review
An absolute pleasure to ski during the day, watch the sunset from the runs, and beautiful night skiing. Quick lifts, great food, and an all around amazing trip.
402FAILS — Google review
Love the mountain just hate the flat spots at the peak as a snowboarder! Nah but a good mountain with trails for everyone.
Chris J — Google review
Lanesborough, MA 01201, USA•Tips and more reviews for Jiminy Peak
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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 3-minute walk away from Lanesborough Country Inn.

Biggins Diggins

4.6
(253)
•
4.4
(16)
Permanently Closed
$$$$affordable
Restaurant
Delivery Restaurant
Nestled in the charming town of Cheshire, MA, Biggins Diggins is a delightful restaurant that caters to all your dining needs. Whether you choose to dine in and soak up the warm ambiance or opt for curbside pickup and no-contact delivery, this eatery ensures a satisfying experience. Known for its allergy-friendly menu and friendly service, Biggins Diggins has become a favorite among locals and visitors alike.
This amazing little restaurant is located just north of Pittsfield, MA with easy access and plenty of parking. We were there during breakfast hours. The “Old Smokey” omelette was perfectly cooked in the middle and full of a delicious variety of smoked meats. The Home fries were some of the best I’ve ever had with the perfect amount of seasoning. I would highly recommend this restaurant for anyone visiting the beautiful Berkshires of Western Massachusetts. I look forward to having an opportunity to return during lunch to sample their other exciting options.
Tim J — Google review
Lovely hometown spot with an extensive sandwich and breakfast menu. Waitress was quick to grab extra horseradish for us and was generally pleasant and personable. Will definitely come back next time we're in town!
Dustin B — Google review
I had a disappointing experience at this restaurant. First, they forgot to bring us our drinks. The food was a let down, especially the brisket - it was so fatty that it was practically inedible. My eggs over medium were barely cooked and runny, and the pancakes were hard on one side. The waitress was nice and acknowledged the issue with the brisket, offering to replace it, but the overall dining experience left me turned off. It's a shame because I was looking forward to a pleasant breakfast with my daughter.
Vinny B — Google review
Allergy friendly, taste bud friendly, and just plain friendly! We've been eyeing Biggins Diggins for a while now and finally decided to go in for breakfast. All I can say is that we should have gone a long time ago! The food was great. Their breakfast menu has some really tasty takes on traditional plates (quality smoke meats and customizable). Almost everything is made from scratch and you can tell that the owners really take pride in their craft and in their place. The portions were good, the ingredients were high quality and fresh, and everything on the menu can be made truly gluten free. That's a big point of difference for them from other places around: They'll cater to the level of gluten intolerance of their customers, be it a preference or Celiac. Our food was filling and delicious, and our coffee was hot and full. The staff was very friendly, welcoming, and happy to chat with us about the restaurant and the menu. The owners were cooking but took the time to come out and say hi since it was our first time in (definitely not the last time). Luckily we went on a quiet winter day, but I can see why this place would have a wait on a nice warm day. The place was clean, welcoming, and well-kept. We'll be back for more! They offer dine in and take out.
Weston M — Google review
So happy to find this place on my way north recently. They opened a few minutes early which was great because I didn’t have a lot of time. It was the waitress’s first day and I was her first customer! Terrific experience. Loved the omelette (interesting shape, very unique), the price was right and I was out of there quickly and back on my way. Loved it, will be back! Recommended.
Kevin J — Google review
Had the s’mores French toast and it was so good! This is such a nice little spot with a family friendly atmosphere - very welcoming. I would eat here often if I lived in the area!
Mandy B — Google review
The food is absolutely delicious, I got an omelette and a Nutella+strawberry French toast. The owner is very friendly, place is nice, food is delicious, I would definitely eat there again.
Suellen H — Google review
Looks like we might have a great breakfast place in the area. The seating area is small and was crowded. As you can see I got the breakfast sandwich with the Taylor ham. Very nice sandwich. Good way to start the day. Staff was friendly and seemed genuinely concerned that my order was correct. I will be back
Kenneth R — Google review
545 S Main St, Lanesborough, MA 01237, USA•(413) 496-3141•Tips and more reviews for Biggins Diggins

Olde Forge Restaurant

4.2
(1293)
•
3.7
(444)
$$$$affordable
American restaurant
Bar
Olde Forge Restaurant is a beloved dining spot with a charming wood interior and friendly staff. The restaurant offers a wide array of menu options, including French onion soup, gourmet grilled cheese, butternut squash quesadilla, loaded mac n cheese, veggie burgers, tenders, and an extensive beer selection. Guests can enjoy the bucolic views from the patio while savoring rare brews and delicious tavern food.
Had a great dinner at Olde Forge! Ate at the bar and the bar tenders were very friendly and helpful. We ordered the Buffalo cauliflower to start, some of the best I've ever had! I was lucky enough to get one of their special Ribeyes. They only get 12 of these a week and it really was outstanding! They did a great job charring the outside just how I like it and keeping the inside a perfect medium / medium-rare. Beers were cold, wine was tasty, price was right! Will definitely come back next time we're in the area. Thanks for a great night Olde Forge!
Donovan T — Google review
Olde Forge Restaurant in Lanesboro, MA has been serving quality food and drinks for more than 40 years. As you enter the restaurant, the interior elicits an odd feel of a rustic, ski chalet and early, settler homestead with wood planking on the walls, dark wooden beams, chairs and tables, and wagon wheel lights. A large bar flanks one side and the dining room the other. Beer and sports memorabilia occupying the wallspace adds a tackiness to the atmosphere that seems to fit. Needless to say it is a very casual, come-as-are, place. There's plenty of parking around the back. And plenty of seating in the original part of the restaurant and the newer rooms in the rear. There's an outdoor deck with tables as well. Remember the ubiquitous Salad Bar and that it vanished during Covid? Here it has returned! My wife and I chose the single visit to the Salad bar and enjoyed the fresh items that were there. Our salads were delicious. Additionally, I chose the Homemade Soup made of potato and sausage prepared in a miniature cast iron pot, served with Oyster Crackers. It was exactly what I hoped and filling! Great homey, comfortable atmosphere with good food.
Gordon S — Google review
10/18/25 second visit. I said to the owner that we were here for 7 days and came to Olde Forge two times. This is certainly the place to hit while in the Berkshires. This is the old world tavern feel. I love the entrance with the brick walls and saloon doors to the dining. The bar I’d loaded with patrons and you can see all the beer steins hanging above head. Tonight I started with their delicious maple old fashioned! Then I ordered their onion soup….delicious. We also ordered the nachos which were per her as well. The wings were awesome, crisp and delicious! For dinner I got their delicious burger with bacon and cheddar and fries, great stuff. My friends had the pork shoulder which they said was delicious and looked tender. My wife had the butter buttered chicken sandwich which She enjoyed. Again, this is a must hit spot. Go early and catch the sunset on the porch! FYI the revue by someone anonymous is not a review to rely on. 10/13/25 We had an awesome dinner at Olde Forge. Jessica our waitress took great care of us and her service was spot on. It’s been a few days since we were there so I don’t remember all the dishes, my apologies. I do regret the Mac n cheese was delicious and creamy! The quesadilla was great as well. My glazed steak was spicy and delicious, very tender. We will be back before heading back to NY. Highly recommended!
Steven T — Google review
I WAS HERE TODAY 7/27 WITH TWO OF MY BESTIE'S SINCE MIDDLE SCHOOL.. THIRTY +YEARS OF FRIENDSHIP.. THE WINGS ARE SO GOOD.. I HAD ORIGINAL AND TRIED THE STICKY SESAME SWEET WINGS.. MOZZARELLA STICKS YUMMY TOO.. I ALSO HAD THE APPLE OAT CAKE.. ALWAYS A GREAT TIME HERE
Nakeisa H — Google review
Came here to eat lunch from out of town, my boyfriend has been going here since he was little and says it changed terribly. They must’ve changed chefs cuz goodness… we walked in and it INSTANTLY smelled like a public bathroom, the stench lingered throughout the whole place, it smells like straight up poop. They have almost NO gluten free items except for salads, i asked about gluten free bread and the waitress snarked at me and said no, I ended up eating a $16 salad (which is only an appetizer), it was not worth it, by the taste it should have been no more than $8. Basically just lettuce and watered down dressing with a dead sardine sitting on top. My boyfriend got a “medium rare” steak that was completely overcooked and the chunkiest “mashed” potatoes possible. A waste of $60. Our waitress only came over one time. We were hoping to have a nice lunch date… but we got this instead. I definitely wouldn’t recommend this place to anyone.
Anonymous — Google review
In the area and decided to try the Olde Forge. They were in the middle of their October Fest weekend festivities but we were still able to be seated quickly. All members of our party ordered the German dishes, and everyone was extremely happy with their meal choices and the amount of food that was served. We are regularly in the area and will very likely be returning to try other dishes.
Christopher H — Google review
We come here often and tonight we brought friends with us. The food is always amazing and we always have good service, until tonight. Our friend ordered a drink -a glass of whiskey NEAT. Every bartender knows that “neat” means no ice, it’s one of the first things you learn. So it was pretty obvious that our server never told the bartender. His drink was delivered on the rocks. She put it on the table and disappeared before he could say anything, so he removed the ice and put it in a water glass. When she came back and we told her, all she said was “Ok.” One friend ordered 6 wings as an appetizer. She only brought one napkin. He asked for “more napkins” and she brought another one. His wife had a wing and also asked for “more napkins” and received one about ten minutes later. I had ordered a dozen wings for my meal. They looked so good—nice and crispy as they should be, and saucy. Unfortunately they weren’t very warm. Someone came in to setup a table next to us so I asked her if they could just be thrown in a microwave for a minute. A couple minutes later, our server came out and said she was having them do a whole new batch. I told her that wasn’t necessary-I didn’t want them to go to waste, just nuke them for a minute and they’ll be fine. That’s all they needed. She said a new batch would be fresh. I told her again it was a waste and that I wanted to eat with my friends. Meanwhile, everyone else was enjoying their meals. About 5 minutes later, she came back out and said the wings had about 10 minutes to go. I pointed out that everyone else would be done with their meals by then, she may as well pack them to go. A few minutes later she returned and said they had been able to switch some meals around in the kitchen and do the new wings quicker. She brought the wings in a container and gave us the Bill. They weren’t crispy at all and had very little sauce. I’ll put them in the air fryer. If only she had nuked the first batch…😞
Cari K — Google review
The food exceeded expectations and so did the service. We had the best experience. Sadie took really good care of us. Just what we needed after a cold walk at the summit of mt greylock! Disregard any negative reviews.
Annette E — Google review
125 N Main St, Lanesborough, MA 01237, USA•https://www.yeoldeforge.com/•(413) 442-6797•Tips and more reviews for Olde Forge Restaurant
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BLUEBiRD & CO.

4.7
(213)
•
4.6
(19)
American restaurant
Bluebird & Co. is a delightful restaurant in Hancock, MA, USA that offers various dining options such as dine-in, curbside pickup, and delivery services. Whether you prefer a leisurely meal at the restaurant, a quick takeout option, or the convenience of having your food delivered to your home, Bluebird & Co. has it all covered. Visitors praise the fresh and delicious food along with the warm and cozy atmosphere of the place.
Great little place! This was on our way home from MA and it did not disappoint! If you are driving Historic Route 20, you should check it out. It was very busy this morning but they did tell us they were down on cooks because of the holiday, which was good! My only complaint is that you should have a sign that says order then go pick a seat. The food was awesome and so were the Lattes. We will definitely go back here!
Sarah S — Google review
Amazing five star servers, service and food! Rachel was our personable hostess, Emily our attentive knowledgeable server, the chef is outstanding and the atmosphere is comfortable and inviting.
Martha H — Google review
Gorgeous interior & outdoor spaces. Very cool vibes. Food was delicious & service was great. Smitty at the bar was pouring beautiful & tasty drinks. Got to say hello to the chef too! Loved the entire visit. Can't wait to come back!
Asteri A — Google review
Really great, creative cocktails, attentive, efficient and friendly service, and great food! What else could you ask for? We ordered the soba noodles, the pasta and the steak frites! All mouth watering delicious! Absolutely in awe on the Mezze group! Another great place to share a meal and memories with friends and family. The authentic Korean flavors were spot on (I’m Korean and felt like my mama was cooking). The outdoor patio was open, creating and expansive and festive experience among nature. Love this cozy spot!
Yuki C — Google review
Located right next to Jiminy Peak Resort, this restaurant has a cute outdoor patio ideal for summer. We loved the blistered green beans, chickpeas, and the gochuchang cauliflower. Def a great place to stop by in the Berkshires!
Anjuli G — Google review
Incredible meal for a large group of 9 with 5 kiddos. Easy to get a reservation last minute. The burger was incredible. The wings were delicious and the drinks were top notch. Our server, Rachel, was a total doll. She helped our kids to have a great time and eat well. Between the folks at our table, we sampled half the menu and all the desserts and we didn’t have a single complaint. Excellent meal start to finish!
Christa G — Google review
Very friendly and welcoming place. Waitress was very friendly and and happily answered all our questions. We both had the Okie Burger. It was delicious and cooked perfectly!
Lee A — Google review
We made a last minute reservation here after our other plans fell through and could not have been happier! Elevated, delicious food in a warm and cozy setting. The service was prompt and excellent. Our server convinced us to try the banana pudding and wowowowow thank goodness we did! Great spot!
Jaimie O — Google review
137 Brodie Mountain Rd, Hancock, MA 01237, USA•https://www.eatatbluebird.com/•(413) 738-9002•Tips and more reviews for BLUEBiRD & CO.

Greylock Grounds Coffee Drive-Thru & Cafe

4.9
(122)
•
5.0
(2)
Permanently Closed
Coffee shop
Greylock Grounds Coffee Drive-Thru & Cafe in Lanesborough, Massachusetts is a popular spot for both locals and visitors. The cafe offers a diverse menu and convenient drive-thru option. Customers can also dine in and enjoy delicious food such as steak tips pizza and Greek salad. The cafe's exceptional service and friendly staff make for a delightful experience, with the added bonus of being located near an antique store for some leisurely browsing while waiting for your order.
We ordered our steak tips pizza and Greek salad and headed over to Berkshire Mantiques to wander around while we waited for our food. Berkshire Mantiques was awesome and I could have wandered for hours. When we received our food… all I can say is amazing. The pizza was like a gourmet treat… the combination of flavor filled steak tips that melt in your mouth, bacon, peppers and onions with cheese and a white sauce was beyond our highest expectations!! The Greek salad was delicious… amazing feta cheese, DELICIOUS dressing, topped with heart shaped cucumbers to add a little extra love!! We ordered iced Carmel coffee for the trip home and a cinnamon bun for breakfast the next day. It was more than just a delicious meal, it was an amazing dining experience. We will go back for sure!!! The owner’s great personality was “the icing on the cake”.
JC D — Google review
Stopped here on a whim last Sunday on a random drive through MA. Best decision ever! Not only was the food delicious, but the service was stellar. The women working were the absolute nicest people and went above and beyond for our pup making her a "pup cup" which is a cup of whipped cream and a TON of bacon. Our girl is a rescue and still a bit skittish so sadly she was weary to take it directly from the girl serving it to her, but happily enjoyed it from the safety of the picnic table 😂 I HIGHLY recommend saving room for a Vanilla Chai Milkshake. Hopefully we find ourselves back out that way again so we can make another stop.
Saraluminum — Google review
So disappointed it took me so long to discover this place. I got a coffee and chef salad. The salad was loaded with fresh veggies and high quality deli meats and cheeses, I was able to get two meals out of it. The coffee was one of the best I’ve had in the area. Prices are very reasonable. Owner is super friendly and nice. I’m really looking forward to coming back and trying one of their paninis.
Sara B — Google review
Loved this! Food was great! Service was exceptional. The people were wonderful and so friendly. Connor was so kind to us and brought our food to us when we waited looking around the antique store across the street. Connor and the team went above and beyond since we got there and made our experience awesome. Would recommend every time !! (Got the breakfast wrap and coffee— so good, also got the harbor trail panini and buff chicken pizza too)
Katherine Y — Google review
We did order two wraps ( one with arugula and another one with bacon )two cheese danish and a large hot chocolate and a medium hot caramel latte. Everything was delicious.
Ludmilla C — Google review
We were camping in Greylock and stumbled across this special place in the morning. The owner was so kind to give us a free delicious scone while we waited for our drinks to be made. Very friendly staff!
Silviana L — Google review
Can NOT recommend this shop enough. The latte was made with quality espresso and didn’t taste like candy (which is how I like it). The cinnamon bun and Apple fritter were GINORMOUS. And the owner was charm itself. Do yourself a favor and stop by immediately.
Elizabeth S — Google review
Great breakfast right near Mt greylock camsite great portions and good breakfast burritos. Even through us some extra scones. A must stop if your passing by
Danny S — Google review
20 Williamstown Rd, Lanesborough, MA 01237, USA•(413) 496-3044•Tips and more reviews for Greylock Grounds Coffee Drive-Thru & Cafe
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Day 2

Northwest side of town
For day 2, we recommend exploring the northwest side side of town. Start the day off with Ashuwillticook Rail Trail, then wind down and take it easy by the time you get to Balance Rock State Park. All together, your day would be filled with about 7 hours of non-stop fun.
1

Ashuwillticook Rail Trail

4.8
(447)
•
5.0
(169)
Park
Outdoor Activities
Hiking Trails
The Ashuwillticook Rail Trail is a 13-mile family-friendly route that was recently extended into Pittsfield, offering opportunities for biking, walking, and even cross-country skiing in winter. The trail follows the path of the old Pittsfield and North Adams Railroad, providing a scenic journey through lakes, forests, and rivers with waterfalls.
We stumbled upon this trail during one of our spontaneous trips to the Berkshires, and it turned out to be a hidden gem. The scenery was absolutely breathtaking, with vibrant fall colors painting the landscape. The trail offered a perfect blend of adventure and romance, making it ideal for either a leisurely stroll or an invigorating hike. As we walked hand in hand, the crisp autumn air and rustling leaves created an enchanting atmosphere. The trail winds through stunning views, with the birch trees standing tall and majestic, adding to the overall charm. Whether you're looking for a peaceful escape or a bit of adventure, this spot is perfect for embracing the beauty of nature on a fall day. We left feeling rejuvenated and inspired, already planning our next visit!
Lela R — Google review
It is springtime in the Berkshires, the birds are singing and the trees are dressing up. It wonderful place to be. The trail is maintained well.
Colin A — Google review
Smoothest pavement and best maintained rail trail we've ever had the pleasure of riding. Saw lots of turtles! Look for them in the murky shallows.
Troy G — Google review
Beautiful Trail ! All paved. Plenty of parking options There was also restrooms located at parking lots and plenty of tables and benches along the way.
Cindy V — Google review
14 miles of paved, clean, beautiful woods, lake and mountain views. This is the nicest bike trail we have used.
Nancy B — Google review
This was a fun place to ride. I’m sure it’s a better place to ride in the summer because it was cold! Nov. 1st is pushing the window. Even riders passing me were telling me how cold they were. The wind really whips out there, and headwinds can be trying. But it was fun. I felt like I was the only person on the path not on an electric bike or a motion-assisted bike.
Paul P — Google review
This is the best rail trail in the far western part of the state. There is no good parking spot at the northern end yet, but you can park on a street nearby. The surface is great.
David B — Google review
We had a blast here, the trail was wide and the scenery was outstanding. We love that the trail was flat and even and there was plenty of parking along it
Stefanie N — Google review
Ashuwillticook, Rail Trail, Cheshire, MA 01225, USA•http://www.mass.gov/eea/agencies/dcr/massparks/region-west/ashuw…•(413) 499-7003•Tips and more reviews for Ashuwillticook Rail Trail
9 min · 3.6 mi
2

Dalton

Dalton, located in Berkshire County, Massachusetts, is a charming town that serves as a transition between the urban and rural areas of the county. Part of the Pittsfield Metropolitan Statistical Area, Dalton had a population of 6,330 according to the 2020 census. The town offers easy access to neighboring areas such as Lanesborough, Lenox, Hancock, and Richmond.
Massachusetts 01226•http://www.dalton-ma.gov/•Tips and more reviews for Dalton
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Adults
2
Children
0
Travelers
2
14 min · 5.5 mi
3

Baker's Golf

4.6
(200)
•
4.5
(7)
Golf driving range
Fun & Games
Miniature golf course
Mini Golf
Baker's Golf Center is a charming mini-golf and driving range facility with a 300-yard driving range and an enchanting miniature golf course. The mini-golf features a picturesque setting with a large cascading waterfall, two ponds, and a flowing brook. The course includes moving obstacles on some holes and small wooden buildings on others, adding to the fun and challenge. It's an ideal place for nature lovers who also enjoy the sport of golf.
We really love having a nice, well maintained, family friendly bowling lane in Pittsfield. The addition of an outdoor 18 hole miniature golf course is a wonderful opportunity to spend more quality time and also enjoy the beautiful Berkshires weather! The course recently opened and we brought the kids today. It’s “pirate themed” which is fun and I am sure as it gains more popularity, they will add even more cool decorations over the years. K&M has revitalized bowling in Pittsfield and now is offering another fun activity for families! I wish them lots of luck and hope that everyone comes to play a round or two.
KAREN C — Google review
Cute little mini golf place. According to their website, this is a women-owned family business. I appreciate that! I always make it a point to assess if an establishment is LGBTQ+ friendly. There isn’t anything that specifically gave me that impression, but also nothing to the contrary. Was very family friendly. The course itself is small but lots of fun obstacles. Fair prices to play. I didn’t use the driving range but it was busy in that area and it all looked very well maintained. Worth a stop in.
Karen C — Google review
We had a great time. We went at sunset it was stunning. The miniature golf course is made with adorable and beautiful 'props' along the way. The staff was super helpful and friendly. One of the staff members even went around with us to take pictures at the end. That was really kind. And of course the 19th whole was a fun added bonus. one of us won a free game. If your in the neighborhood i would definitely recommend dropping by.
Esther P — Google review
Decent mini golf, $9 a person and driving range. Plus a few fun yard games.
Robert Q — Google review
Great miniature golf course. It is very well maintained and has fun hoes.
Jennifer C — Google review
Super cute and fun minigolf nice time to spend. Driving range was nice and big with both shaded tee boxes and grass
Aria S — Google review
Driving range and mini golf only. No restroom. The basket of 120 golf balls was $10. Good value. Mini golf for seniors was $7.
Kay P — Google review
Definitely a fun time and experience for someone who's never been golfing before Definitely would recommend this place 👏🏾
Jason R — Google review
633 S Main St, Lanesborough, MA 01237, USA•http://bakers-golf.square.site/•(413) 443-6102•Tips and more reviews for Baker's Golf
11 min · 0.54 mi
4

Pontoosuc Lake

4.8
(73)
•
4.0
(4)
Lake
Pontoosuc Lake in Lanesborough is a picturesque destination offering various water activities such as swimming, boating, and fishing. The lake's calm waters are perfect for kayaking or paddleboarding, while its sandy beach provides a relaxing spot to bask in the sun. Although smaller than Onota Lake, Pontoosuc Lake boasts scenic views and is popular among boaters.
Absolutely bea utifo as always
C A — Google review
The fish were biting here also.
Dan D — Google review
Good fishing
Larry G — Google review
Beautiful, scenic lake with views of the surrounding mountains. Free parking and a boat launch. Pathways and picnic tables are throughout. Nice place to eat lunch and walk by the water's edge.
Steve C — Google review
Beautiful, clean, not crowded and relaxing!! Easy to boat, board, go tubing and float on rafts.
Robinette M — Google review
Beautiful lake and some nice hiking in the area. There were pontoon boats all over the place when we were there and it just felt like this big, warm community with the people we met. Just wonderful.
Mark B — Google review
Nice lake , went out the beach side , just a warning the bathrooms and changing rooms are closed , so yeah that's unfortunate , come prepared
Danny B — Google review
Out of your number of Lakes in the area I would Say Pontuusac is definitely one of the cleaner and nicer lakes in the area to visit compared with that of a Onota Lake definitely would prefer swimming or visiting here any day.
Jon C — Google review
Massachusetts•Tips and more reviews for Pontoosuc Lake
6 min · 2 mi
5

Savoy St

Savoy St is a popular destination for casino party rentals, serving various nearby areas such as Dalton, Lanesborough, Hinsdale, Lenox, Hancock, and more. It offers convenient access to those looking to host events in the surrounding regions including Cheshire, Lee, Stockbridge, Adams and beyond.
Pittsfield, MA 01201, USA•Tips and more reviews for Savoy St
11 min · 3.4 mi
6

Balance Rock State Park

4.6
(21)
•
4.0
(13)
State park
Nature & Parks
Balance Rock State Park offers a range of recreational activities, such as hiking, dog walking, and mountain biking. Visitors can also admire the impressive Balancing Rock, a remnant from the Glaciers. The park occasionally has horses and their droppings from nearby farms and properties, as well as people using ATVs and dirt bikes. Some trails lead to private property or connect with the State Forest. The iconic rock is easily accessible for exploration, surrounded by numerous picnic tables.
Amazing Park is good for hiking, dog walking, or mountain biking. Also, just for enjoying the namesake, the Balancing Rock leftover from the Glaciers. There can be horses(or just their piles) from nearby farms and properties as well as people using atvs and dirt bikes. Some of the trails lead off to private property and also to the State Forest.
Patrick D — Google review
The rock itself is a site to see. You can park right next to it and walk around it. Many picnic tables are located around the rock. There are hiking/walking/ATV trails in the park as well. However, none of them are very well marked. The park could help itself by marking these and/or providing maps. Overall, nice place to go.
Ryan M — Google review
My daddy, his siblings & his cousins grew up on Balance Rock Road. It was known as Bouchardville. My granddaughter is the 4th generation of Bouchards to play in this park & walk the trails.
Michele ( — Google review
We love going here every year!
Nicole C — Google review
Nice place. Car can go near to the stone. There are multiple tables for picnic.
Raj T — Google review
This is a quiet, lovely place to just walk around. The rock is awesome but my favorite part is just walking around the area. It seems so apart from the world, even though it is just a mile or so off a main road. Parking is very close so easy to get to without being a strenuous walk.
Penny G — Google review
It's a cool place to see and just sit there and wonder how the rock became perfectly balanced in the air. It does have some graffiti unfortunately that was blacked out with black spots. They kind of get in the way of photography. There's a hiking trail that branches off from the rock and fairly easy to find.
Alexander V — Google review
Well kept park for a quick picnic lunch... would like to see the graffiti cleaned rather than just painted over...
Konrad M — Google review
Balance Rock Rd, Pittsfield, MA 01201, USA•https://www.mass.gov/locations/pittsfield-state-forest•Tips and more reviews for Balance Rock State Park
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Where to eat

Even the most seasoned adventurers need a break to chow down some food. Close to Baker's Golf, these restaurants are about a 4-minute walk away.

Lanesboro Pizza

4.3
(218)
•
4.2
(28)
$$$$cheap
Pizza restaurant
Lanesboro Pizza is a restaurant in Lanesborough known for its delicious pizzas. They offer a variety of mouth-watering options such as the Krispy Cone Deluxe Burger and the Blue Cheese Burger. Customers have raved about their superb pizza, which has a great crust and an excellent flavor combination. The owner of the restaurant is friendly and welcoming, creating a pleasant dining experience for guests. Lanesboro Pizza also provides great service and is highly recommended by visitors.
Really a take out pizza place, but we ate in at a couple of tables that are available. The pizzas are large and the owner mixed a half and half for us as we couldn't decide what to have. Couple of beers while we waited and a chat with the owners as it was a quiet night. Great experience.
Nev B — Google review
Wow! We just got pizza from here and it is dynamite! The man who served us was so pleasant too. We aren't from the area but come every fall for a weekend and without a doubt will be back here for more pizza!!! I'd even send Dave portnoy here if he'd take the ride! That good. And drive up pizza service is so cool!
Tammie L — Google review
Excellent choice for travellers staying at Club Wyndham Bentley Brook. We ordered the Lanesboro special, Vegetarian, cheese pizza and kids spaghetti meals. Pizza was ready in 15 minutes.
Fiona — Google review
Price is different from website and if you say something about it they're very rude this is what we paid since prices went up. We always get calzones and they're usually really huge, This last time the calzone was really small!!! Prices went up their menu price Website was calzone starts at $9 plus 75 cents ON for a topping now calzones are $10 plus a dollar for some toppings and $2 for other toppings was expecting to pay less and it was more $25plus for 2 calzones and when I called and asked about the price difference the lady was kind of rude about it and said it's not our menu even though it's a Google menu trying to say I was on a different website they don't want to pay Google that's why their website hasn't been updated
Michael C — Google review
Service was fast and as promised, but agree with several of the other posters that the pizza was average, perhaps slightly better than can be grabbed in the frozen food aisle. It met our needs for a meal.
Samantha U — Google review
The pizza here is amazing. The crust is the perfect combination of soft on the inside and crispy on the outside. The ingredients all tasted fresh and of good quality. They even serve it to you right on the tray they cook it on which keeps it nice and warm the whole time. We hope to come back soon.
Drew B — Google review
Chicken souvaki salad was very good. Drive up window very convenient and they even gave my a dog a treat.
Tony P — Google review
Legit worst pizza I’ve ever had…basically middle school pizza…avoid at all costs
Requiem A — Google review
739 S Main St, Lanesborough, MA 01237, USA•https://lanesboropizzeria.wordpress.com/•(413) 442-0600•Tips and more reviews for Lanesboro Pizza

Brookhouse Sports Pub & Restaurant

4.2
(474)
•
3.1
(9)
$$$$affordable
American restaurant
Nestled in the charming town of Lanesborough, Massachusetts, Brookhouse Sports Pub & Restaurant is a delightful spot that caters to both casual diners and those looking for a quick meal. The inviting atmosphere makes it perfect for enjoying a cozy sit-down dinner or grabbing something on the go. Guests rave about the delicious menu options, including standout dishes like the Black Diamond Steak, which surprises with its freshness and expert seasoning.
We stopped in to get food. I was interested in the Black Diamond Steak which I haven't had in years. I was expecting a processed piece of meat. Wrong. It was a wonderful fresh piece of steak beautifully spiced and cooked to perfection! It was definitely loud as a Patriots game was on.
Marc G — Google review
A nice night out with coworkers. I had 2 Kentucky Bourbon Ales to drink and Hot honey chicken sandwich with tater tots to eat. Service was good.
Carrie T — Google review
Wow! This place is an awesome restaurant to check out. We dined outside. The wait staff for fantastic, our meals were so delicious, and moderately priced. It's a great place to watch sporting events.
New A — Google review
Love the out door dining expirence. The food is good. The staff is great. I enjoyed my brookhaus pasta with salmon ♡ my friend also enjoyed her crispy chicken sandwich.
Nicole S — Google review
Had a better taste left in my mouth from 45 minutes in a dentist chair and better overall experience. Spent an hour more than I should have there experiencing scrappy food and worse service but I was starving.
Timothy S — Google review
This place is a vibe! Really good food and drinks. A perfect gathering place for lunch or after work. Their wings are super good and the service is great even on a busy day.
Tierre M — Google review
Stopped in today for wings and salad. Was not disappointed. Crispy and flavorful wings. Nice selection of beers on tap. I'll be back very soon! Friendly staff.
Stephanie A — Google review
Just really upsetting I come for the bruschetta pesto chicken pasta But now the portions are smaller for $21. I will not be coming anymore. Bummer.
Danielle L — Google review
650 Cheshire Rd, Lanesborough, MA 01237, USA•http://thebrookhousepub.com/•(413) 499-3331•Tips and more reviews for Brookhouse Sports Pub & Restaurant
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Lakeside Bar & Grill

3.9
(625)
•
2.8
(26)
Temporarily Closed
$$$$affordable
Restaurant
Nestled in the scenic town of Lanesborough, MA, Lakeside Bar & Grill is a delightful dining spot that captures the essence of lakeside charm. This restaurant has become a beloved destination for both locals and visitors alike, thanks to its inviting atmosphere and mouthwatering menu. Guests can enjoy fresh seafood dishes alongside vibrant salads while sipping on refreshing drinks. The stylish interior complements the stunning outdoor seating area, where patrons can soak in beautiful views while enjoying their meals at picnic tables.
The fish and chips were delicious! (and homemade) Started with pretzel bites and while a bit deflated/flat they hit the spot. Loved the fries, dipped them in a side of spicy aoli and found it amazing. Dessert was the fried Oreo sundae, seemed like they wrapped the Oreos in a pastry dough before frying them and I have no complaints the dessert was a perfect balance of rich chocolate and creamy vanilla. One complaint: my partner ordered a chipotle chicken sandwich and asked for no bacon due to medical reasons and it still arrived with bacon. I ate the bacon and it was amazing, but again we asked for none. Server was so polite, view is lovely I'm writing this review while we watch the ducks and boats on the lake. Will be back, dunno when, but I'm full and still craving more.
Bethany M — Google review
We went to out for a girls night at 6:30 on a Thursday evening. The 6 of us were seated outside within 10 minutes. We then waited about 10 minutes for a drink order to be taken, not a problem. We ordered our food and that's when this review takes a turn for the worse. We waited over an hour for the food to be served. The table next to us waited so long that when their food arrived cold they opted to just leave. Our food came out sporadically...and the portion sizes would not have filled a toddler. A tiny very overcooked burger with about 7 French fries on the plate was $18. My daughter and her friend ordered the specials. Appetizer if chili cheese fries came and again was about 7 to 10 fries. The dinner special of mini hot dogs wrapped in bacon and served with French fries at a cost of $12 was small portion size, but also came very over done shriveled up, served in a ripped open dinner roll with again less than a handful of fries. One person in our party ordered food to take home. After about a half hour of us sitting waiting to pay the waitress returns to tell us they are out of one of the items ordered. While sitting outside if the sun goes down there is absolutely no lighting, so we had to use phone flashlights to pay our overpriced for what we got bill. We will not be returning.
Michelle M — Google review
Super excited we found this gem. The lobster roll was my first and it was divine! I didn’t expect to like the clam chowder, but it was so good! The kids even enjoyed it! Apparently it’s made fresh daily and that attention and preparation really shows. The staff was great and you can’t beat the lake view.
Andrea N — Google review
I ordered a hot lobster roll. It was a little bit small for 36$ imo. I love sweet potato fries so I'm happy that was an option. The sweet potato fries were okay, crispy but oily at the same time. The lobster was fresh and was cooked well. The bun was a cheap hot dog bun you would buy at dollar general. Nice lakeside location with plenty of outdoor seating at picnic tables. The service was good and attentive. Nothing on the menu about dietary substitutions and I did not ask.
Amanda S — Google review
This place was recommended by the the local celebrity, The Viral Viking. It's clean and has a great atmosphere. The bartender and manager have a fantastic dynamic that make it feel like home. The swiss mushroom burger was very tasty on its brioche bun! Super light and fluffy. The calamari was deep fried to perfection. Extra crispy with out being over cooked. The chicken breast was juicy and the zucchini were grown locally with a lovely seasoning. Definitely stop by!
Nick F — Google review
Loved it ! Small crowd. Live music - Talented guy playing guitar singing GREAT, classic oldies !! They let me buy my Sam Adam's beer glass for $5 - as a Souvenir of my Memories of a FABULOUS SUMMER in Boston.. Thanks !! I'll go back !!
Karen J — Google review
I didnt eat so I can't rate food. Just moved in down the road..love that I can walk here.! On the lake. Great views. Patio seating. Live music when I visited. He was FAB! PERFECT PRE HOLIDAY VIBES HERE!
Mary S — Google review
It looks good, but there can't have been two ounces of fish in my fish sandwich, a tiny little sliver of about 85% breading. Between that; the overcooked (or more likely reheated) fries; slow service and slow kitchen; and complete lack of any kind of covid protocol, it's not a place I will ever want to go back to. They get two stars because of the good views.
David A — Google review
750 S Main St, Lanesborough, MA 01237, USA•(413) 496-3042•Tips and more reviews for Lakeside Bar & Grill

Zucchini's

4.4
(876)
•
4.0
(292)
$$$$affordable
Italian restaurant
Zucchinis is a cozy restaurant that serves a mix of American and Italian cuisine, including wood-fired pizza, veal marsala, and hamburgers. The restaurant operates for lunch and dinner on weekends and only offers dinner on weekdays. Zucchinis caters to various dietary preferences with its vegetarian, vegan, and gluten-free options. Customers have praised the attentive service and pleasant ambiance, featuring comfortable seating and a lovely fireplace.
The food here is amazing. We shared a zucchini stack appetizer then I had the rigatoni with shrimp and scallops. So tasty! Great service and relaxed atmosphere. One of our go to spots on our annual Berkshires trip!
Roxana B — Google review
Our waitress Laurie took care of us when we walked in my wife had the salmon. The salmon was cooked to perfection, but the veggies were a little undercooked. My sister-in-law had the airport chicken with mashed potatoes and veggies again the veggies weren’t cooked, but everything else was done, right And I had the veal Parmesan with angel hair pasta the veal Parmesan was very dry but the martinis were very wet overall they got an eight out of 10
James G — Google review
Zucchini’s Italian restaurant atmosphere is good , service is good , food also good except my main cost I have Oder mix seafoods with risotto cost me $38 I just noticed that no grill lobster on my plate and when I asking about that server said they running out of lobster But we do replace that with scallop (with out inform until customer asking ) but however a starter so good , I do recommend this place but just make sure everything is going right!!
Tummasa F — Google review
Usually a great place to eat and have an enjoyable meal. Unfortunately, I picked the lasagna this last visit. It was extremely salty with no other taste to it. First time I had a bad meal there in all the years I have eaten there. Scratch that meal off the list when I eat at Zucchini's again.
Jill W — Google review
Wow, I had an amazing meal. The grilled salmon was great over the veggie medley with Fingerling potatoes Erica was excellent! Super friendly and Very attentive. Best experience I’ve had here by far.
Di V — Google review
We ordered the airline chicken dish and the veal parmigiana. The airline chicken was the size of a piece you would get on an airline. It was extremely dry. My husband ordered the veal parmigiana. It was very thin and tough. We both had pasta. The pasta was extremely salty. When I told the manager that I wasn’t happy with my chicken, she responded well that’s the way airline chicken is. She wasn’t kind but did offer a different dish. However I did not want to wait for another dish. The server was kind and attentive. But that didn’t take away the fact that our overall experience was unsatisfactory.
Susan S — Google review
Catered food for a store event. Everything arrived hot and ready. Great selection, price and variety of dishes and sizes from the catering menu. A big hit with all of our associates. Thank You so much!
George K — Google review
Zucchini’s is my go to for any brunch or evening gathering. Recently held a rehearsal dinner party and the food and service were fabulous. Zucchini’s never disappoints. Thank you to Lynne and her incredible staff!
Kim O — Google review
1331 North St, Pittsfield, MA 01201, USA•http://www.zucchinisrestaurant.com/•(413) 442-2777•Tips and more reviews for Zucchini's
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Day 3

Proximity is everything
For day 3, we bundled attractions like Pittsfield State Forest and Hancock 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 5 hours.
1

Pittsfield State Forest

4.5
(223)
•
4.2
(41)
State park
Nature & Parks
Hiking area
Public wheelchair-accessible bathroom
Pittsfield State Forest is a sprawling natural haven that beckons outdoor enthusiasts year-round. Spanning 11,000 acres, this expansive state park boasts 30 miles of diverse trails catering to hikers, mountain bikers, and skiers. The forest also encompasses tranquil campsites and Pontoosuc Lake for boating, swimming, and fishing.
Great place! Gene at the ranger station was TOP NOTCH! Awesome facilities and a great experience PLUS most of the tent sites come with a "Bonus Skunk". Just let her do what she do, she cool!
Michael M — Google review
Such a beautiful place. Very generous sites that allow for privacy. Fire pits but no grill. I'll come back.
Karen T — Google review
Scenic, accessible, and well maintained, what else do you want in a state park? We stayed for a weekend camping. The hiking trails are well marked. The bathrooms are very well maintained. My comfort station at the main campground area had a dishwashing station, hot showers locks on the doors, lockable door on the family room, and nice bathrooms with flush toilets.
Marc T — Google review
Was amazed with the park great hiking trails. The bathroom and shower is newer than other parks that I have visited.
Chris H — Google review
The Pittsfield State Forest, near the Lulu trailhead—a playground for outdoor enthusiasts and their canine companions. With a multitude of hiking trails, it's a place where every path seems to whisper, "Explore me." While some trails show the wear and tear of nature's forces, they remain navigable for those with a sense of adventure. The absence of trash barrels serves as a subtle reminder to tread lightly and respect the land. It's not just a haven for hikers and their four-legged friends; mountain bikers will find the terrain equally inviting. With slopes that offer just the right blend of challenge and exhilaration, it's a spot where rubber meets dirt in the most satisfying way. All in all, it's a place that offers a little bit of rugged paradise for everyone.
Gralok L — Google review
It was a nice spot for my girlfriend and her kids to stay but when we switched the reservation to my name and she left her set up for me is when we had problems, drunks came crashing into our site hit the fire pit almost ruined our tent all DCR did was call state police who did nothing. They didn’t address the alcohol even though the rules clearly state no alcohol allowed. Now get woken up told I’ve been here for two weeks leave and don’t come back, which is false I’ve been here less than a week, my gf and her kids were here a month. Don’t camp here unless you enjoy near death experiences and drama.
Andrew D — Google review
I love this place, every time I go it's a different experience. There is trails for every one, with nice little views all over the mountain. Even if you don't want to hike there is picnic spots with grills, a beach area with white sands. If you drive half way up there is a view spanning over new york and a quant little pond. When I went today with my pup it was beautiful clear skys at the bottom, once I got to the top it was a foggy new world.
Ryan W — Google review
Very nice area. Berry Pond is really great. You can just stick around for a long time. The whole area is so peaceful and birds chirping is very soothing. We just decided to give it a try and we were very pleasantly surprised. If I am in the area again, I will sure consider visiting again.
Pranav B — Google review
1041 Cascade St, Pittsfield, MA 01201, USA•https://www.mass.gov/locations/pittsfield-state-forest•(413) 442-8992•Tips and more reviews for Pittsfield State Forest
33 min · 15.8 mi
2

Hancock

Hancock, located in Berkshire County, Massachusetts, is a small town with a population of 757. It is part of the Pittsfield Metropolitan Statistical Area and offers visitors a glimpse into the Shaker community through the well-preserved buildings and traditional crafts at Hancock Shaker Village. The town's unofficial general store, coffee house, and post office can be found at The Country Store at Jiminy Peak.
Massachusetts, USA•Tips and more reviews for Hancock
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Popular road trips from Lanesborough

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Lanesborough to
Rochester
Lanesborough to
Rochester

What's the weather like in Lanesboro?

It depends on when you visit! We've compiled data from NASA on what the weather is like in Lanesboro for each month of the year: see the links below for more information.

  • Weather in Lanesboro in January
  • Weather in Lanesboro in February
  • Weather in Lanesboro in March
  • Weather in Lanesboro in April
  • Weather in Lanesboro in May
  • Weather in Lanesboro in June
  • Weather in Lanesboro in July
  • Weather in Lanesboro in August
  • Weather in Lanesboro in September
  • Weather in Lanesboro in October
  • Weather in Lanesboro in November
  • Weather in Lanesboro in December

All road trips from Lanesborough

  • Lanesborough to Rochester drive
  • Lanesborough to Rochester drive

Explore nearby places

  • Lanesboro
  • Pittsfield
  • Hancock
  • Lenox
  • Adams
  • Williamstown
  • North Adams
  • Stockbridge
  • Charlemont
  • Great Barrington
  • Bennington
  • Shelburne Falls
  • Albany
  • Hudson
  • South Deerfield
  • Northampton
  • Dover
  • Amherst
  • Arlington
  • West Springfield
  • Schenectady
  • Brattleboro
  • Agawam
  • Springfield
  • Manchester
  • Saugerties
  • Saratoga Springs
  • Litchfield
  • Hunter
  • Kingston
  • Millbrook

All related maps of Lanesboro

  • Map of Lanesboro
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  • Map of Hancock
  • Map of Lenox
  • Map of Adams
  • Map of Williamstown
  • Map of North Adams
  • Map of Stockbridge
  • Map of Charlemont
  • Map of Great Barrington
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  • Map of Amherst
  • Map of Arlington
  • Map of West Springfield
  • Map of Schenectady
  • Map of Brattleboro
  • Map of Agawam
  • Map of Springfield
  • Map of Manchester
  • Map of Saugerties
  • Map of Saratoga Springs
  • Map of Litchfield
  • Map of Hunter
  • Map of Kingston
  • Map of Millbrook

Lanesboro throughout the year

  • Lanesboro in January
  • Lanesboro in February
  • Lanesboro in March
  • Lanesboro in April
  • Lanesboro in May
  • Lanesboro in June
  • Lanesboro in July
  • Lanesboro in August
  • Lanesboro in September
  • Lanesboro in October
  • Lanesboro in November
  • Lanesboro in December

Looking for other day-by-day itineraries in Lanesboro?

Check out our other curated itineraries that are also filled with jam-packed days:

  • 1-Day Lanesboro Itinerary
  • 2-Day Lanesboro Itinerary

Day itineraries for nearby cities

  • 3-Day Albany Itinerary
  • 3-Day Saratoga Springs Itinerary
  • 3-Day Springfield Itinerary
  • 3-Day Kingston Itinerary
  • 3-Day Schenectady Itinerary
  • 3-Day Brattleboro Itinerary
  • 3-Day Northampton Itinerary
  • 3-Day Pittsfield Itinerary
  • 3-Day Manchester Itinerary
  • 3-Day Bennington Itinerary
  • 3-Day Lenox Itinerary
  • 3-Day Hudson Itinerary
  • 3-Day Amherst Itinerary
  • 3-Day Saugerties Itinerary
  • 3-Day Shelburne Falls Itinerary
  • 3-Day Williamstown Itinerary
  • 3-Day Great Barrington Itinerary
  • 3-Day Litchfield Itinerary
  • 3-Day North Adams Itinerary
  • 3-Day Charlemont Itinerary
  • 3-Day Stockbridge Itinerary
  • 3-Day Dover Itinerary
  • 3-Day Agawam Itinerary
  • 3-Day Hunter Itinerary
  • 3-Day Arlington Itinerary
  • 3-Day Millbrook Itinerary
  • 3-Day South Deerfield Itinerary
  • 3-Day West Springfield Itinerary
  • 3-Day Adams Itinerary
  • 3-Day Hancock Itinerary
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