There are certain destinations we know we’ll visit some day, but for one reason or another, they sit on the back burner. Since moving to New York City over a decade ago, I knew my time with the Berkshires would eventually come. Earlier this summer, at long last, it finally did.
If you’re familiar with this highland region in western Massachusetts, it may have something to do with Edith Wharton, who famously relocated here in pursuit of “the real country.” Or Herman Melville, who wrote Moby Dick from a desk overlooking Mount Greylock, said to be the inspiration for his white whale. Or perhaps you’ve heard of Tanglewood and Jacob’s Pillow, prolific music and dance centers, respectively. If you’re an art lover, MASS MoCA is likely on your radar. Wellness enthusiast? The concentration of pioneering spas (like Canyon Ranch) is notable. And for the leaf peepers, the area’s astonishing fall landscapes are probably on your bucket list.
But how did the Berkshires come to be such a swirl of interests? “This area has often been described as a cultural vortex,” Scott Edward Cole tells me. He and his partner Frank Muytjens are the owners of The Inn at Kenmore Hall (my home base for this excursion). “As creative people ourselves, we are nurtured in so many ways.”
Cole suggests the natural landscape is what initially attracts creative types to the Berkshires. And then, the proximity to Boston and New York. “It became a popular summer escape in the advent of railways, and during the Gilded Age many grand homes, referred to as ‘cottages’, were built by families like the Vanderbilts, Carnegies, and Choates,” he explains.
A view of Mount Greylock in North Adams, Massachusetts.Photo: Getty Images
“In the 1900s, there was more of a cultural critical mass,” Cole says in reference to a small music festival that grew to become Tanglewood (the summer home of the Boston Symphony Orchestra), as well as the Jacob’s Pillow Dance Festival (now America’s largest and longest-running international dance festival). Summer stock theater such as the Williamstown Theater Festival and Berkshire Theatre Festival also brought major stars from film and Broadway to local stages. “And of course,” Cole adds, “Norman Rockwell moved to Stockbridge and immortalized the people and places of his daily life here.”
Throughout the decades, the Berkshires have continued to thrive as a creative bubble, with chefs, hoteliers, and artists decamping to towns such as Lenox, North Adams, and Great Barrington. Even still, destinations like the Hudson Valley and Catskills continue to overshadow their well-rounded neighbor to the east in terms of tourism. I have a hunch why, and it’s because I’m guilty of it: convenience. For New Yorkers, the Berkshires require more commitment to reach than, say, Beacon or Kingston. A visit means going the extra mile, booking the rental car another day, staying one more night. And I think that’s a good thing. Say what you will about a low lift, but it’s usually those further afield locations that make for the more compelling travel experiences.
