Guidebook for Stockbridge, West Stockbridge, Lenox, GB + more!
Essentials
Big Y World Class Market
10 Pleasant Stfood store
food store, like a local Whole Foods only better!
2 Locations: Lenox and GB
248 locals recommend
Guido's Fresh Marketplace
760 S Main Stfood store, like a local Whole Foods only better!
2 Locations: Lenox and GB
Queensboro Wine & Spirits
26 Main Stbeer and wine
Public Market
8 Main Stessentials and a deli
Loeb's Foodtown of Lenox
42 Main Stsmall food store, essentials
Nejaime's Wine Cellar
3 Elm Stbeer, wine, liquor, cheese
Elm Street Market and Tiffany's Cafe'
4 Elm Stessentials and deli
Food Scene
Frankie's
80 Main StItalian! Great for families, excellent food!
Patisserie Lenox
30 Church StFuel Bistro/ Coffee Shop
293 Main StRouge Restaurant
3 Center StHaven
8 Franklin StBerkshire Mountain Bakery Inc
367 Park Stthe best bread, really, the best
Pizzeria Boema
84 Main Stwood oven pizza - amazing!!
it is now Cafe Triskele - the food is insanely amazing, you have to go here!!
24 locals recommend
Chez Nous Bistro
150 Main Stit is now Cafe Triskele - the food is insanely amazing, you have to go here!!
High Lawn Farm
535 Summer Stbest ice cream on planet earth
Cafe Adam, Bar and Restaurant
420 Stockbridge Rdgreat food, sit in the bar area or outside
burgers and fries but great burgers and fries! (plus more)
this is a roadside house, so bring chairs, a cooler and sit on the lawn and enjoy!
47 locals recommend
The Bistro Box
937 S Main Stburgers and fries but great burgers and fries! (plus more)
this is a roadside house, so bring chairs, a cooler and sit on the lawn and enjoy!
Cantina 229
229 Hartsville-New Marlborough Rdfood is amazing. on a farm. you must go here but need a reservation.
voted best atmosphere for a restaurant in MA, home cooked meals
21 locals recommend
Pleasant and Main Cafe General Store
1063 Main Stvoted best atmosphere for a restaurant in MA, home cooked meals
Brooklyn vibe, well-known NYC chef-owned. True farm to table plus pizza.
203 locals recommend
The Prairie Whale
178 Main StBrooklyn vibe, well-known NYC chef-owned. True farm to table plus pizza.
Bizen Gourmet Japanese Restaurant and Sushi Bar
17 Railroad Streetsushi
The East Asian Cuisine
305 Stockbridge Rdsushi
Brava
65 Church Stsmall tapas-style, cool atmosphere
Soco Creamery
5 Railroad Stlocal ice cream shop in GB
The Lost Lamb
31 Main Stpastry shop in town - a must visit!
Shots Cafe
27 Housatonic Stpastries, sandwiches, coffee, breakfast, lunch and ice cream!
The Olde Heritage Tavern
12 Housatonic Stlocal bar
John Andrews
224 Hillsdale Rda drive but great food
candlelight dining, an experience. quiet, more formal and romantic.
72 locals recommend
The Old Inn On The Green
candlelight dining, an experience. quiet, more formal and romantic.
Arts & Culture
Norman Rockwell Museum
9 Glendale RdNot sure yet if they are doing the weekday 5-6pm free shows or not...
257 locals recommend
Jacob's Pillow
358 George Carter RdNot sure yet if they are doing the weekday 5-6pm free shows or not...
Shakespeare & Company
70 Kemble StNaumkeag
5 Prospect Hill RdThe Mount, Edith Wharton's Home
2 Plunkett Stgardens and sculptures and history!
MASS MoCA
1040 Mass MoCA WayThe Clark Art Institute
225 South StTanglewood
a bit of a drive but a cool area and if you enjoy wild art sculptures its worth it!
310 locals recommend
Art Omi
1405 Co Rte 22a bit of a drive but a cool area and if you enjoy wild art sculptures its worth it!
Berkshire Theatre Group
6 East StTurn Park Art Space
2 Moscow RdHancock Shaker Village
1843 W Housatonic StBerkshire Botanical Garden
5 W Stockbridge RdEntertainment & Activities
Kripalu Center For Yoga & Health
57 Interlaken RdClosed until August 2021
Bousquet Ski Area
101 Dan Fox DrCatamount Aerial Adventure Park
17 Nicholson RdPhoenix Theatres Beacon Cinema
57 North Stmovies
Yoga Great Barrington
30 Elm CtYoga spot!
Radiance Yoga
401 North Stanother good yoga spot
Parks & Nature
Kennedy Park
275 Main StBeat spot for miles of easy trails
Beartown State Forest
69 Blue Hill RdGreat trail around the lake and good for a swim!
Our go to hike but gets packed. Go really early or end of day.
112 locals recommend
Monument Mountain Reservation
Our go to hike but gets packed. Go really early or end of day.
October Mountain State Forest
317 Woodland RoadMount Washington State Forest
143 East StreetLaura Lookout Tower
Stockbridge Bowl
Town beach isn’t great but it’s still access to the lake
Lake Garfield
Town beach is great
Tyringham Cobble Park
20 Jerusalem RdOlivia's Overlook
Hiking Trails2 nice hiking trails
tallest mountain in MA! plenty of hiking trails or you can drive to the top!
39 locals recommend
Mount Greylock State Reservation Visitor Center
30 Rockwell Rdtallest mountain in MA! plenty of hiking trails or you can drive to the top!
Bullard Woods
easy trails
Arcadian Shop
91 Pittsfield RdOutdoor store for all outdoor needs!
Ice Glen Trail
Ice Glen TrailEasy trail, magical forest.
Drinks & Nightlife
The Red Lion Inn
30 Main StMooncloud
47 Railroad StDare Bottleshop & Provisions
11 Housatonic StreetCurated wines, food and other delights!
Traveler advice
Getting around
Weekend Crowds!
In general, the weekends are packed here so take advantage of weekdays as there will be fewer people!