Inside: Discover Extraordinary Living
Known colloquially as “the Brooklyn of the Berkshires,” Great Barrington effortlessly blends a hip, semi-urban feel with the relaxed creative vibe that the Berkshires is known and loved for. Funky and charming, the town offers great restaurants and boutique shopping along with being a haven for the arts. Music and film festivals make their summer home in Great Barrington while Bard College at Simon’s Rock offers lectures and performances year-round. The town is also ideally situated to Berkshires arts hotspots Tanglewood and Jacob’s Pillow. The outdoors beckons as well in Great Barrington, with plentiful hiking trails and swimming holes as well Ski Butternut resort, which offers 22 downhill trails. It’s easy to see why the town is popular as both a getaway vacation destination and a year-round community.
Here are some of the best things to eat, buy, see, and do in Great Barrington:
Shopping

One Mercantile + sett
8 Castle St, Great Barrington
These sister stores, located in Great Barrington’s historic downtown area, couldn’t be cuter: One Mercantile is a home goods and gift shop offering small-production, fair-trade, and vintage reproduction items, while sett focuses on specialty tabletop items. Both shops are owned by a vintage-loving couple, who opened the stores to share their appreciation for well-crafted and artisan goods. Expect adorable home décor items like candles, tea towels, and throw pillows as well as women’s accessories and hip baby and kid clothing at One Mercantile, while sett is well stocked with everything you could ever need for your table, including linens, flatware, serving pieces, and bar tools.
Dining

Marjoram + Roux
47 Railroad St, Great Barrington
Whether you snag a spot inside or enjoy one of the handful of outdoor café tables, you’re going to want to linger at this breakfast/lunch/provisions spot located inside a former chocolatier’s space. On offer are popular dishes such as daily frittatas, a farro salad with local greens, and a variety of sandwich and paninis as well as coffee, tea, espresso, cappuccino, and decadent pastries. Marjoram + Roux also offers a selection of prepared meals to go.

Prairie Whale
178 Main St, Great Barrington
While nearly every restaurant claims to be farm-to-table these days, Prairie Whale is the real deal. The owners support an evolving circle of vegetable and livestock farmers, cheesemakers, and foragers, and the restaurant offers a butchery and charcuterie program that produces dry-aged grass-fed steaks, bacon, and other whole-animal products. Popularized through coverage in Vogue, The New York Times, The Boston Globe and others, Prairie Whale is a hip and lively spot with ample outdoor seating (often accompanied by live music) and a rotating seasonal menu filled with simple yet outstanding fare. The drinks program includes craft-brewed beers, natural wines, and unique cocktails boasting fresh ingredients from the restaurant’s garden.
Culture

Mahaiwe Performing Arts Center
14 Castle St, Great Barrington
The Mahaiwe Performing Arts Center brings high-quality live performances to stage and screen right in the heart of Great Barrington. With a focus on highlighting regional talent and a mission to strengthen the local community, theatergoers at Mahaiwe are treated to a diverse range of music, dance, drama, and comedy programming. Educational and family-focused arts events are also on offer at the restored, historic theater, as well as special events like the annual auction and gala fundraisers.
Seasonal

Great Barrington Farmers Market
18 Church St, Great Barrington
Saturdays in Great Barrington start with a stroll through the farmers market, located right downtown and running from mid-May to Mid-November each year. The 100% producer-only market includes everything from vegetables, fruit, cheese, bread, honey, jams, and maple syrup to farm-fresh pork, chicken, lamb, and beef to herbs, flowers, and plants, as well as a sweet lineup of baked goods and other treats. Visitors will also find food to munch on, such as tacos and egg sandwiches. This community gathering spot is a must-try.

Berkshires Arts Festival
Ski Butternut, 380 State Rd, Great Barrington
Rated by the Berkshires Visitors Bureau as one of the 10 must-see Cultural Hotspots in Western Massachusetts, the Berkshires Arts Festival is a 4th of July weekend tradition, now in its 22nd year. More than 150 juried artists are on hand, offering the finest of ceramics, leather, jewelry, sculpture, and photography. In addition, the event also includes artist workshops, live music, food, wine, and a puppet show. This year’s event will run from Saturday July, 1 through Monday, July 3.