Great Barrington, MA Travel Guide: The Most Charming Town in the Berkshires

In less time than it would take to read Edith Wharton’s Ethan Frome, you could be having your own charmed experience in the Berkshires. While the masses flock to the Catskills, an upstate region that’s become a satellite community for Brooklyn weekend expats, you could head east of the Hudson River to the Southern Berkshires destination: Great Barrington (just 20 minutes south of Wharton’s “first real home” in nearby Lenox). The quaint brick town is just as charming as fictitious Starkfield, but with an artful undercurrent and cultural relevance that’s worthy of its two-and-a-half-hour-drive from New York. “Part of the town’s appeal is that it’s not too reachable—getting here requires logistics and planning, so there’s a sense of successfully preserving what makes this place so special,” local travel consultant Rebecca MacGregor tells Vogue.

While The Berkshires have persisted as a haven for nature-lovers and artists alike, in the last few years, it’s developed a new draw: young New Yorkers. With a slew of new businesses and improvements to existing cultural institutions, Great Barrington has become one of the most popular destinations in the highlands of Massachusetts. The town is pulsing with a revival that not only evokes appreciation for its long-standing appeal, but also an evolution that’s representative of our farm-to-table loving, environmentally conscious generation. It’s so charismatic, you might find yourself lured to the real estate listings window as you sip a fresh cup of spiced apple cider from the farmers market on a crisp day. According to the Berkshires’ own premier real estate agency, the age of metropolitan couples that flock exponentially to the Great Barrington area has skewed considerably younger over the last few years.

Photo: Getty Images

Unlike the Catskills Mountain region, which is far more sprawled out and punctuated only by quaint, post-industrial towns that are a little out of the way from the nature you drove up to see, Great Barrington lies at the foot of Monument Mountain and Mount Everett. Officially named an Appalachian Trail community in 2009, laying out a welcome mat and resources to the millions of hikers that pass through each year, the scenery is a constant reminder of all the possible activities to be enjoyed.

With over 7,200 acres of state forest and hundreds of easily accessible trails only moments from the town’s center, visitors truly choose their own adventure. Take a cinematic cruise down the long flat farm roads, cooing at highland cattle and relaxed quarter horses, or stop to collect a local farmer’s bounty in exchange for a few dollars in the honor system jar. Climb to one of the various summits overlooking the Housatonic River and pause to marvel at the natural ponds and more evergreens than you ever expected to find south of Vermont. Pick up the local Shoppers’ Guide and bounce from antique fair to tag sale to barn sale, collecting rare and valuable items that haven’t yet been priced with a tourist’s inflation. Walk around town while sipping a clean, mindfully-sourced cup of coffee from Ilse, and satisfy a sweet tooth with ice cream from SoCo Creamery or a bag of rare licorice from Coco’s Candy Shop. Ski, snowboard, or snowshoe at Butternut or Catamount in the winter. Take a dip in the Green River in the summer. Play an IRL game of Go Fish with Berkshire Rivers Fly Fishing. Enjoy cuisine that rivals some of New York’s best, and art galleries and live music that you can experience without ever having to move your car. Afterward, if you can bear to part with the town, a drive back to New York is supremely scenic. But why not spend the night at a local inn, which is likely snuggled up to a babbling brook or farmstead? There you’ll understand what makes Great Barrington so great.

Here, your weekend guide to this perfect Berkshire town.