The Berkshires Best Guidebook
Food scene
Organic and local crepes, sandwich’s, salads and more. Vegan and gluten free options. Good coffee, tea, and smoothies. Can be busy in peak times but we’ll worth the wait.
40 locals recommend
Starving Artist Creperie and Cafe
40 Main StOrganic and local crepes, sandwich’s, salads and more. Vegan and gluten free options. Good coffee, tea, and smoothies. Can be busy in peak times but we’ll worth the wait.
Fuel Bistro/ Coffee Shop
293 Main StGood coffee
Berkshire Mountain Distillers
356 S Main StHilltop Orchards Home of Furnace Brook Winery
508 Canaan RdBizen Gourmet Japanese Restaurant and Sushi Bar
17 Railroad StreetThe Prairie Whale
178 Main StRubiner's Cheesemongers
264 Main StThe Old Inn On The Green
*Seasonal only. High quality roadside spot. Burgers, fries, and some creative other options. Big outdoor space for frisbee, etc. Long lines in peak times so be prepared to wait.
47 locals recommend
The Bistro Box
937 S Main St*Seasonal only. High quality roadside spot. Burgers, fries, and some creative other options. Big outdoor space for frisbee, etc. Long lines in peak times so be prepared to wait.
Recently open seasonally. Call before heading there. Coffee and drinks only.
82 locals recommend
No. Six Depot Roastery & Cafe
6 Depot StRecently open seasonally. Call before heading there. Coffee and drinks only.
Lenox Coffee
52 Main StGreat coffee. No food served.
Dotties Coffee Lounge
444 North StA great coffee stop on your way to northern destinations
Ice cream and shop. Local farm to come ice cream. Jersey cows you can see up close.
32 locals recommend
High Lawn Farm
535 Summer StIce cream and shop. Local farm to come ice cream. Jersey cows you can see up close.
Lucky's Ice Cream & Grill
30 W Center StDistrict Kitchen & Bar
40 West StCafe Adam, Bar and Restaurant
420 Stockbridge RdAyelada
505 East StGreat Barrington Bagel Company
777 S Main StA really nice lounge atmosphere in downtown Great Barrington with high end cocktails and light fare.
17 locals recommend
Mooncloud
47 Railroad StA really nice lounge atmosphere in downtown Great Barrington with high end cocktails and light fare.
Cantina 229
229 Hartsville-New Marlborough RdOutdoors
Outdoor activities and things to do
Cold swim holes on hot days. The Green River is a great spot to cool down.
8 locals recommend
Green River
Cold swim holes on hot days. The Green River is a great spot to cool down.
A popular hiking destination with two ways up. Head left from the bottom for a longer more gentle hike. The top has expansive views and some areas with shear cliff drops. Best to keep dogs leashed and kids close.
53 locals recommend
Monument Mountain
A popular hiking destination with two ways up. Head left from the bottom for a longer more gentle hike. The top has expansive views and some areas with shear cliff drops. Best to keep dogs leashed and kids close.
Activities available in the summer, fall, and winter
329 locals recommend
Catamount Mountain Ski Resort
78 Catamount RdActivities available in the summer, fall, and winter
Ski Butternut
380 State RdA family friendly local resort with tubing and skiing/snowboarding
Jiminy Peak
37 Corey RdVery good mountain bike trails and frisbee golf course. Brewery with outdoor seating and a few fire pits. Note there are no rentals so you have to bring your own gear.
17 locals recommend
Norbrook Farm Brewery
204 Stillman Hill RdVery good mountain bike trails and frisbee golf course. Brewery with outdoor seating and a few fire pits. Note there are no rentals so you have to bring your own gear.
Head into the New York State entrance side for a nice long gentle hike on man-made paths that are also accessible for strollers and wheelchairs
282 locals recommend
Bash Bish Falls State Park
Falls RoadHead into the New York State entrance side for a nice long gentle hike on man-made paths that are also accessible for strollers and wheelchairs
Cold river swimming with fun little waterfalls. Usually a pretty quiet place. Stop at the Southfield Store before or after for food and drinks.
33 locals recommend
Umpachene Falls Park
Umpachene Falls RoadCold river swimming with fun little waterfalls. Usually a pretty quiet place. Stop at the Southfield Store before or after for food and drinks.
Nice easy hike. 20 mins. The glen has a windy trail that you need to scuttle through but is nice and cool on a hot day and very pretty in winter. Once you cross the suspension bridge, cross over the railroad tracks and head up the trail. Stay right at the split. Usually people turn back at the end and return back the same way.
There is also a stroller/wheelchair accessible path along the river as an alternative.
28 locals recommend
Ice Glen Trail
Ice Glen TrailNice easy hike. 20 mins. The glen has a windy trail that you need to scuttle through but is nice and cool on a hot day and very pretty in winter. Once you cross the suspension bridge, cross over the railroad tracks and head up the trail. Stay right at the split. Usually people turn back at the end and return back the same way.
There is also a stroller/wheelchair accessible path along the river as an alternative.
Kennedy Park
275 Main StNetwork of easy to moderate hiking trails
Lake beach and walking path loop. Take your favorite floatable out on the water. A 3 minute walk from our space. The walking path (backside of the parking lot) is stroller/wheelchair accessible.
49 locals recommend
Lake Mansfield Park
Lake Mansfield RoadLake beach and walking path loop. Take your favorite floatable out on the water. A 3 minute walk from our space. The walking path (backside of the parking lot) is stroller/wheelchair accessible.
Race Brook Falls
Moderately challenging hike
Arts and Culture
Classic Americana artwork by Norman Rockwell. Beautiful grounds and facilities.
Norman Rockwell Museum
9 Glendale RdTanglewood is a very popular summer music venue. Several venues within but it’s popular to bring a picnic and sit on the large green space. Be prepared to walk a good distance. You can rent chairs there if you don’t want to carry them and there’s a variety of food options.
398 locals recommend
Tanglewood
Tanglewood is a very popular summer music venue. Several venues within but it’s popular to bring a picnic and sit on the large green space. Be prepared to walk a good distance. You can rent chairs there if you don’t want to carry them and there’s a variety of food options.
Mahaiwe Performing Arts Center
14 Castle StVery unique industrial repurposed space. Often hosts music concerts and has a brewery, cafe, and food as well.
382 locals recommend
MASS MoCA
1040 Mass MoCA WayVery unique industrial repurposed space. Often hosts music concerts and has a brewery, cafe, and food as well.
Barrington Stage Company
30 Union StWorld class dance company. Very accessible to all. Free outdoor shows throughout the week in the summer. Get there early for a seat up close or else bring a chair of your own.
257 locals recommend
Jacob's Pillow
358 George Carter RdWorld class dance company. Very accessible to all. Free outdoor shows throughout the week in the summer. Get there early for a seat up close or else bring a chair of your own.
The Mount, Edith Wharton's Home
2 Plunkett StChesterwood
4 Williamsville RdSightseeing
Railroad Street
Railroad StreetMany great restaurants, cafes, galleries, and shops. Easily walkable.
Great place to visit with different exhibits throughout the year. The Fall Harvest festival is always a lot of fun.
118 locals recommend
Berkshire Botanical Garden
5 W Stockbridge RdGreat place to visit with different exhibits throughout the year. The Fall Harvest festival is always a lot of fun.
Health & Wellness
Just down the street from our space on the way to town. Family friendly sessions as well.
LifeWorks Studio
50 Castle StJust down the street from our space on the way to town. Family friendly sessions as well.
Beautiful views and hiking trails on the property.
122 locals recommend
Kripalu Center For Yoga & Health
57 Interlaken RdBeautiful views and hiking trails on the property.
Body & Soul
184 Maple AveA local well-regarded place for body work/massage.
Indoor swimming pool and warm pool. Basketball court/gym and workout facilities. Day passes available.
14 locals recommend
Berkshire South Regional Community Center
15 Crissey RdIndoor swimming pool and warm pool. Basketball court/gym and workout facilities. Day passes available.
Groceries
Guido's Fresh Marketplace
760 S Main StA local grocery with a good selection.
Berkshire Food Co-op
34 Bridge StIn-town groceries and supplies
Big Y World Class Market
10 Pleasant StLarger grocer with a good selection including beer/wine.
Price Chopper
300 Stockbridge RdThe only grocer open later night in town
Outdoor Gear
Berkshire Bike and Board
29 State RdArcadian Shop
91 Pittsfield RdPlaine's Bike Ski Snowboard
55 W Housatonic St