The bucolic town of Great Barrington is nestled in The Berkshires area—a region renowned for its scenic vistas. Its picturesque countryside is dotted with charming towns, majestic mountains, tranquil lakes, and lush forests.

Beyond the serenity of the great outdoors, The Berkshires boasts an array of enticing activities regardless of the season. From art museums and cultural institutions to vibrant musical performances, and live theater, there’s always something to explore. Nature enthusiasts will be lured by outdoors pursuits such as hiking, biking, kayaking, and the splendor of fall foliage. For those who prefer a bit more action, there’s mountain biking, downhill- and -cross-country skiing, golfing, and beyond.

There’s also a bounty of topnotch restaurants, chic boutiques, and serene spas to satisfy every desire. Browse the below listings for some ideas on planning for your stay. Please note, for your convenience, estimated driving times are listed.

Culturally Connected: Museums, Theater & Music

Aston Magna Music Festival (1 minute)
BPL Berkshire Playwrights Lab (2 minutes)
Barrington Stage Company (36 minutes)
Bennington Museum (1 hour and 18 minutes)
Berkshire Botanical Garden  (16 minutes)
Berkshire Choral International  (17 minutes)
Berkshire Museum  (35 minutes)
Berkshire Theatre Group (15 minutes)
Chesterwood Museum (17 minutes) *Please note: this museum closes during the winter season
The Clark (1 hour and 3 minutes)
The Guthrie Center at the Old Trinity Church (7 minutes)
Jacob’s Pillow (33 minutes)
MASS MoCA (1 hour and 8 minutes)
Mahaiwe Performing Arts Center (3 minutes)
The Mount, Edith Wharton’s Home (21 minutes)
Music Mountain (33 minutes), Located in Falls Village, Connecticut
Naumkeag (14 minutes)
Norman Rockwell Museum (18 minutes)
Shakespeare & Company (21 minutes)
Tanglewood Music Center (22 minutes)
Williams College Museum of Art (1 hour and 4 minutes)
Williamstown Theatre Festival (1 hour and 3 minutes)

The Great Outdoors

Appalachian Trail (25 minutes)
Ashuwillticook Rail Trail (56 minutes)
Berkshire Aviation Enterprises  (7 minutes)
Berkshire Bike & Board (3 minutes)
Berkshire Canoe Tours (24 minutes)
Berkshire East Mountain Resort (1 hour and 20 minutes)
The Blanford Golf & Tennis Club (41 minutes)
Bousquet Ski Area (29 minutes)
Catamount Ski Area (15 minutes)
The Clark (public park), (1 hour and 3 minutes)
Crab Apple Whitewater (1 hour and 28 minutes)
Egremont Country Club (public golf course) (8 minutes)
Furnace Brook Winery at Hilltop Orchards, (Nordic skiing/full moon hikes/general hiking) (26 minutes)
Housatonic River Walk (2 minutes)
Jiminy Peak Mountain Resort (47 minutes)
Mt. Everett State Reservation (30 minutes)
Maple Corner Farm (cross country skiing and snow shoeing) (44 minutes)
Monument Mountain (9 minutes)
Natural Bridge State Park (1 hour and 12 minutes)
Notchview (56 minutes)
Otis Ridge (25 minutes)
Ski Butternut (7 minutes)
Spirit Ballooning (22 minutes)
Wahconah Falls State Park (49 minutes)
Zoar Outdoor (1 hour and 19 minutes)

Bites & Beverages

Aroma Bar and Grill Indian Restaurant, 413-528-3116 (5 minutes)
Barrington Brewery & Restaurant (6 minutes)
Bizalion’s Café-Market, 413-644-9988 (5 minutes)
Bizen Gourmet Japanese Restaurant and Sushi Bar, 413-528-4343 (3 minutes)
Blantyre (The Bistro, The Conservatory, and The Champagne Salon) (23 minutes)
Twoflower Cafe 34 Railroad St., Great Barrington, 413-645-3548 (3 minutes)
Café Adam (7 minutes)
Donaji Mexican Restaurant, 413-717-4220 (5 minutes)
Eat on North (35 minutes)
Elixir  (2 minutes)
Fuel Coffee Shop (1 minute)
Great Barrington Bagel Company, 413-528-9055 (6 minutes)
Methuselah Bar and Lounge (35 minutes)
Naji’s (5 minutes)

The Prairie Whale (1 minute)
Rubiner’s Cheesemongers & Grocers (1 minute)
Siam Square Thai Cuisine (1 minute)
SoCo Creamery (1 minute)
The Stagecoach Tavern (17 minutes)
The Well (1 minute)
Xicohtencatl (4 minutes)

Relax & Rejuvenate

Canyon Ranch (22 minutes)
Cranwell Spa and Golf Resort (21 minutes)
Miraval Berkshires Resort & Spa (20 minutes)

Shop Great Barrington

Asia Barong, (Asian art imports)
Berkshire Baby
Casa B Group/GB9 (fashions for her)
Catwalk (upscale women’s resale shop; proceeds benefit the Berkshire Humane Society)
The Chef’s Shop
Griffin (vintage fashion, home goods, art, furniture, books, and toys)
Karen Allen Fiber Arts
Tom’s Toys
Mistral’s Home
Next Consignment
One Mercantile Goods & Gifts
Tasha Polizzi (apparel, home furnishings, and accessories for her and him)