When I arrived in Great Barrington, Massachusetts to kick-off a weekend in the country, I was struck by the feeling that I wasn’t the only New Yorker around. Among the uber-trendy farm to table restaurants and art galleries, I noticed an abundance of stylish, modern country homes, places I could easily imagine successful creatives penning their memoirs “away from it all.” But, by the end of my weekend, I realized that while these mountains are most definitely an oasis for hipsters, a refreshing authenticity can be found if one ventures to look beyond the Pendleton flannels.
From the charming, gray-haired history buff who mesmerized the crowd at the Norman Rockwell Museum, to a waitress who hailed from my childhood home of upstate New York (and explained that she finds The Berkshires more peaceful—and cheaper), I was taken by the people I met in these mountains.
Aside from making small talk with everyone you meet, here are a few must-try activities for an idyllic weekend in Western Massachusetts.
Friday night: If arriving in style is your thing, consider chartering a Wings Air helicopter to take you from New York to The Blantyre hotel in Lenox, Mass.—the chopper shuttles passengers from city to country in just an hour and a half. The 117-acre Relais & Châteaux property is a luxurious, historic estate where guests can cross-country ski, snowshoe or ice skate in the winter (in warmer months, golf, tennis and swimming are just some of the activities on offer). Art lovers willing to travel a bit further (roughly four hours by car from NYC; three from Boston) can check-in to The Porches Inn at Mass MoCa, where they’ll stay in a restored Victorian row house with a porch overlooking the expansive museum, steps away from enough installations, performances and exhibits to send one down a modern art rabbit hole for an entire weekend.
Saturday morning: Head to Stockbridge to walk its adorable Main Street before plunging deep into nostalgia at The Norman Rockwell Museum. The late artist called the town home from 1953 until his death in 1978. His most famous works, including the Four Freedoms paintings, hang in the museum, and from May through November you can also tour his studio, which was moved—building and all—to the site from its original location in downtown Stockbridge.
Saturday afternoon: Embrace the inevitable deep, Americana-induced thoughts swirling in your head with the most American of beverages: a cold beer. While the area is home to quite a few breweries (and wineries, and distilleries), I recommend Barrington Brewery. Powered almost completely by solar panels, its beer list runs the gamut, and the space’s inviting, cozy-casual atmosphere encourages lingering.
Saturday evening: Great Barrington is also home to Prairie Whale, an absolute must-try restaurant helmed by Mark Firth, a restaurateur who garnered serious industry buzz when he traded Brooklyn and Marlow & Sons for life in the country. After one meal there I can say that his risk was well worth it. The seasonal menu changes by the day, and in the winter months you’re likely to find savory, comforting dishes with a modern twist. This is a place for meat eaters: Animals are butchered on-site and charcuterie, sausage and bacon are made in-house. Those whose nights don’t end at dinner should check the schedules of the many performing arts venues in the area for evening entertainment. In the summer you can catch performers from the Boston Symphony Orchestra at Tanglewood, in Lenox, or a performance at Jacob’s Pillow, a National Historic Landmark which hosts an annual festival of dance in addition to exhibits, classes and more. In the colder months, Mahaiwe Performing Arts Center is a great indoor alternative. The historic destination feels like an old-time, small town movie theater and offers live performances and films all year round (bonus: it’s close to Prairie Whale in Great Barrington).
Sunday morning: No matter where you are in the Berkshires, chances are there’s an antique shop nearby just waiting to be explored. I recommend checking out the fine china at Elise Abrams Antiques, in Great Barrington, and the vintage clothing and records at 7 Arts Gift Shop, in Stockbridge.
Sunday afternoon: To take in one last beautiful view of the Berkshires, you’ve got to sweat a little. Thankfully, there are as many hiking and biking trails as there are antique shops, and each is more scenic than the next. One popular bike route is the 3.6 mile trek frequented by Norman Rockwell himself, which takes you from Main Street in Stockbridge to Lake Averic. More trails can be found at berkshires.org.