Hayley’s guidebook
Food scene
Cheese and Charcuterie in an intimate setting. Outdoor seating is available. They do not take reservations.
50 locals recommend
Brava
65 Church StCheese and Charcuterie in an intimate setting. Outdoor seating is available. They do not take reservations.
Old Mill
53 Main StUpscale and modern fare, in a beautiful setting
Bistro Zinc
56 Church StRefined takes on French fare
STEAM Noodle Cafe
286 Main StRamen
Artisanal pizza with GF and vegan options. Outdoor seating is available
20 locals recommend
Pizzeria Boema
84 Main StArtisanal pizza with GF and vegan options. Outdoor seating is available
Chee's | Chinese Cuisine
13 Columbia StCantonese, Szechuan, and Polynesian food
Alta
34 Church StFrench bistro with a hopping bar scene. Outdoor seating is available.
Delicious burgers. Outdoor seating only. The lines can get long, so go early and check the website for their hours.
47 locals recommend
The Bistro Box
937 S Main StDelicious burgers. Outdoor seating only. The lines can get long, so go early and check the website for their hours.
Cafe Lucia
80 Church StGreat Italian food
Romantic farmhouse setting with a patio. Serves locally sourced American Fare
99 locals recommend
John Andrews
224 Hillsdale RdRomantic farmhouse setting with a patio. Serves locally sourced American Fare
Trattoria and Pub. Outdoor seating and live entertainment.
15 locals recommend
20 Railroad Public House
20 Railroad StTrattoria and Pub. Outdoor seating and live entertainment.
New American eats, a buzzing bar with porch seating. Live music on Fridays.
30 locals recommend
Firefly Gastropub & Catering Co.
71 Church StNew American eats, a buzzing bar with porch seating. Live music on Fridays.
Freight Yard Restaurant & Pub
1 Furnace StAmerican cuisine and casual dining
The Courtyard: Provides a picturesque garden setting for lunch or dinner from June through September. No reservations.
117 locals recommend
The Red Lion Inn
30 Main StThe Courtyard: Provides a picturesque garden setting for lunch or dinner from June through September. No reservations.
Mazzeo's Ristorante
1015 South StFine Italian dining, voted Best of the Berkshires
Truc Orient Express
3 Harris StVietnamese cuisine
Chez Nous Bistro
150 Main StCharming French bistro
Frankie's
80 Main StGreat Italian food with outdoor seating available.
Seasonal American fare in a modern setting, plus craft brews and cocktails.
54 locals recommend
District Kitchen & Bar
40 West StSeasonal American fare in a modern setting, plus craft brews and cocktails.
MINT - Lakeside Indian Dining & Bar
435 Laurel StCasual setting with views of Lake Laurel.
Salmon Run Fish House
78 Main StFamily-owned bar and eatery.
Cozy European style bistro featuring continental cuisine. Outdoor seating available.
11 locals recommend
Once Upon a Table
36 Main StCozy European style bistro featuring continental cuisine. Outdoor seating available.
Quaint eatery dishing up woodfired pizzas, burgers, pastas and sandwiches.
14 locals recommend
Roasted Garlic
483 W Housatonic StQuaint eatery dishing up woodfired pizzas, burgers, pastas and sandwiches.
Rustic taverna with covered outdoor patio providing Greek provisions & known for grilled whole fish.
24 locals recommend
Aegean Breeze Restaurant
327 Stockbridge RdRustic taverna with covered outdoor patio providing Greek provisions & known for grilled whole fish.
Breakfast, Brunch and Coffee
locally focused American eatery, plus gluten-free & vegan fare.
40 locals recommend
Starving Artist Creperie and Cafe
40 Main Stlocally focused American eatery, plus gluten-free & vegan fare.
The Lost Lamb
31 Main StNo. Six Depot Roastery & Cafe
6 Depot StFuel Bistro/ Coffee Shop
293 Main Sttwoflower Great Barrington
34 Railroad StreetDotties Coffee Lounge
444 North StTunnel City Coffee
100 Spring StShots Cafe
27 Housatonic StBlueberry Hill Market Cafe
515 US-20Haven
8 Franklin StFlo's Diner
1245 W Housatonic StHidden gem of the Berkshires
Sightseeing
Benedict Pond Loop
Lake Mansfield Park
Lake Mansfield RoadOtis Reservoir
one of the most scenic and remote lakes in the Berkshires!
one of Massachusetts' most beautiful parks, featuring a spectacular waterfall - the highest in the state!
282 locals recommend
Bash Bish Falls State Park
Falls Roadone of Massachusetts' most beautiful parks, featuring a spectacular waterfall - the highest in the state!
Richmond Pond
available for swimming, fishing, and boating with public access
Monument Mountain Reservation
October Mountain State Forest
317 Woodland RoadFlag Rock
Olivia's Overlook
Hiking TrailsShaker Mountain
Basin Pond
4-22 Becket RdStevens Glen Trail Head Richmond, MA
Lenox RoadHollow Fields
Perry Peak RoadBerkshire Activities
Crab Apple Whitewater Inc
2056 Mohawk TrailWhitewater rafting and kayak trips
Tanglewood
Performing Arts Center
Hancock Shaker Village
1843 W Housatonic Stlandmark destination and museum
Norman Rockwell Museum
9 Glendale RdSki Butternut
380 State RdSkiing, snowboarding, and tubing
Ioka Valley Farm
3475 Hancock RoadFun for families, activities change season to season
Bousquet Ski Area
101 Dan Fox DrSkiing and summertime adventures
Jiminy Peak
37 Corey RdSkiing, snowboarding, mountain adventure park. Fun all year round.
Naumkeag
5 Prospect Hill RdPublic garden and historic home
MASS MoCA
1040 Mass MoCA WayMuseum of contemporary art; largest in the United States!
Magic Wings Butterfly Conservatory
281 Greenfield RdButterfly conservatory and gardens
The Mount, Edith Wharton's Home
2 Plunkett StThe Clark Art Institute
225 South StExceptional art and architecture
Berkshire Botanical Garden
5 W Stockbridge RdOne of America's oldest botanical gardens
Berkshire Art Museum
159 E Main StContemporary art exhibitions
Jacob's Pillow
358 George Carter Rddance center and performance art space
Mahaiwe Performing Arts Center
14 Castle StTurn Park Art Space
2 Moscow RdOutdoor sculpture museum
Catamount Mountain Ski Resort
78 Catamount RdSkiing, aerial adventure park, ziplining and more!
Shopping and Specialty Markets
Nejaime's Wine Cellars
60 Main StRobin’s Candy
288 Main StDépart Wine, Beer & Beverage
28 Railroad StGuido's Fresh Marketplace
760 S Main StLoeb's Foodtown of Lenox
42 Main StStop & Shop
876 State RdBizen Gourmet Japanese Restaurant and Sushi Bar
17 Railroad Street