Great Barrington, Massachusetts | Could You Live Here?

Great Barrington, Massachusetts, just might be the tastiest small town in New England.

At some point in the last few decades of its 255-year history, Great Barrington became Chef Central, and on this random Saturday the southern Berkshire town teems with diners and shoppers, despite the deep November chill. Cars circle like hungry cats, prowling for parking with easy access to restaurants on Main Street or Railroad Street (aka Restaurant Row). Post-lunch shoppers, fresh off their farm-to-fork meals, duck into Patisserie Lenox for a French pastry pick-me-up or a lick of darkly velvet Dirty Chocolate at SoCo Creamery.

Those more inclined to work it off might be climbing Monument Mountain—a boulder-strewn peak with Berkshire views where Nathaniel Hawthorne and Herman Melville hiked and talked, sparking the genesis of Moby Dick. Or strolling the River Walk along the Housatonic, parallel to Main Street, that starts at the W. E. B. Du Bois River Garden Park just steps from where the famed African American writer and activist was born. The Appalachian Trail Conservancy (ATC) has designated the town an “Appalachian Trail Community,” for its dedication to the legendary nearby trail. In winter, you can burn calories at Ski Butternut, a family-oriented ski area with 22 trails and über-affordable season tickets. In summer, you’re in the Berkshire cradle of the arts, less than a half hour from Tanglewood or Jacob’s Pillow.

All factors, no doubt, in Great Barrington being named #1 in Smithsonian magazine’s “20 Best Small Towns in America of 2012.” So whether the final head count is 60 or 70 restaurants (potato, potahto, as they say), suffice it to say that the main difficulty facing a visitor or transplant will be narrowing down your choices. Or go for broke and work your way through the full menu of eateries celebrating the lineage of local foods. Delicious.

The Setting

Equidistant from NYC and Boston (2¼ hours), the vibe here leans more toward Brooklyn than Beacon Hill. Lucky residents have their pick of venues like Tanglewood (Lenox), summer home to the Boston Symphony Orchestra; Jacob’s Pillow Dance (Becket); and the Berkshire Theatre Festival (Stockbridge), for starters. Not to mention local spots like Arlo Guthrie’s Center at the Old Trinity Church, immortalized in Alice’s Restaurant, where Guthrie’s Troubadour series defies musical definition. Nearby spas and retreats run the gamut from Canyon Ranch (Lenox) to Kripalu (Stockbridge), surrounded by the rolling beauty of the Berkshires offset by endless farmland.

Social Scene

You hear the word constantly: culture. “Great Barrington has a good balance,” says Kirsten Fredsall, who works the counter at Farm & Home when she’s not selling real estate in the back, at Brockman Real Estate. “It’s got easy access to NYC, a very vibrant downtown, it’s easy to shop, and it’s got a small-town feel, but with culture.” The historic Mahaiwe Performing Arts Center, a restored 1905 vaudeville house in the center of town, hosts headliners like Tony Award-winner Audra McDonald, Lucinda Williams, and Art Garfunkel. The Berkshire International Film Festival blazes into the downtown for four days in June, but the BIFF is also a resource year-round and welcomes volunteers.

Eating Out

Support of local farmers is fierce and visible. The sleek, woodsy beauty of Allium is a backdrop to its contemporary small plates—farro with radishes, squash, and pecorino, or Maplebrook burrata cheese with hazelnut crumbs. The Prairie Whale’s Mark Firth is a renowned Brooklyn transplant who raises pigs, sheep, and chickens, thus guaranteeing the provenance of Sunday’s crunchy fried chicken brunch and an arugula salad with eggs bright as the sun. And we’re just getting started. “It’s impossible to get a bad meal in Great Barrington,” says innkeeper Lynda Fisher at the Inn at Sweet Water Farm, who is no slouch in the kitchen herself (see below).

Shopping

Some of these shops smell so good you want to move in: Mistral’s, for French country; Farm & Home, for a handcrafted gentleman farmer’s look. Karen Allen Fiber Arts displays toasty-warm knitted things, including the actor/director’s own line of cashmere wear. And cheese is rightly raised up on a pedestal at Rubiner’s Cheesemongers & Grocers—classes include “Intro to Cheese,” and on this November afternoon, noted food writer Ruth Reichl is signing her latest book surrounded by massive wheels of milky perfection.

Real Estate

Recently, an in-town Victorian with three bedrooms and views of the Housatonic from the deck listed at $285,000, while a four-bedroom New Englander in a pretty neighborhood in walking distance to town priced at $359,000. “The Hill,” up Taconic Avenue, is desirable and pricey, from $700,000 to $800,000, although a building lot was selling for $129,000. Look for more reasonably priced homes around Christian Hill Road.

Resident Perks

Beyond the obvious—some of the best restaurants in New England at the tip of your fork—you’ve got skiing in your own backyard at family favorite Ski Butternut, with 22 trails, tubing, a ski school, and affordable tickets. And tucked away on 275 bucolic acres, there’s Bard College at Simon’s Rock, a four-year liberal arts college for super-motivated kids.

Getting Your Bearings

At Lynda Fisher and Andrei Vankov’s beautiful Inn at Sweet Water Farm, a wall of cookbooks keeps company with breakfast feasts of eggs from backyard chickens, pear-almond tarts, and kefir from a culture Andrei brought back from Russia. In town, the charming Wainwright Inn has been operating since 1766. 

This feature was first published in the November/December 2016 issue of Yankee Magazine.