“Who goes to the Berkshires? Nobody goes to the Berkshires,” quips Ramona Singer on “The Real Housewives of New York.” “The Berkshires is more for people who can’t afford the Hamptons!” While I would never argue per capita income with Ramona, I would agree: If you’re seeking a step-and-repeat red carpet scene or an arrive-in-your-helicopter oceanside retreat, then the Berkshires may not be a good destination for a second-home — or even a long-weekend getaway — for you.
But maybe you’re reading this while simmering poolside in South Florida, your sweltering summer imperceptibly slipping away into fall. Or maybe you’re sitting in bumper-to-bumper traffic on the MacArthur Causeway (as a passenger, of course). Maybe you’re thinking that as much as you love the local vida loca and sun-soaked climate, it’s time to fly north.
Mountains flaming with gay rainbow-colored fall foliage? Sure, that’s nice, but what’s an über-cool queer like you going to do in the country? Well, how about some world-class culture? Add to that a steady stream of social influencers from New York City and Boston and a local farm-to-table food revolution within one of the most scenic settings in the eastern United States.
South Floridians and gay friends of Ramona Singer, I give you the Berkshires! Setting: a patchwork of small towns in rural western Massachusetts all connected by high hills. Just two and a half hours from New York City, the area borders New York on the west and Connecticut and Vermont to the south and north, respectively.
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The Berkshires is home to some of the most spectacular fall foliage displays, as well as acclaimed arts festivals like the Tanglewood Music Festival, Jacob’s Pillow Dance Festival and the Berkshire Theatre Festival. It’s also the historic home of artists and literati — think: Edith Wharton, Herman Melville and Norman Rockwell. Known for its storied inns, liberal attitudes and postcard settings, the Berkshires practically kickstarted the gay destination wedding industry — long before the unions were even recognized.
Sorry, Ramona, but the Berkshires is actually a great progressive place that offers something for every type of traveler.
The Leaf Peeper
Let’s start with the money shot. After all, you did leave behind a week at your local beach to see a five-star foliage show. For peak season, you’ll want to arrive around mid-October. Recommended route: an eight-mile, high-drama ride with hairpin turns up Mount Greylock. At 3,491 feet, it is the highest natural point in Massachusetts and part of the Appalachian Trail. Hike it if you must, but if you’re a Floridian through and through — more acclimated to sea-level — then may I suggest the more scalable Monument Mountain, located just south in the funky little town of Great Barrington?
For a mash-up of scenic views, the deep gorges of Bash Bish Falls State Park, which straddles the border between Great Barrington and New York, offers a walk-in-the-woods-with-cascades experience. The falls are often ranked among the best in the state.
The Coffee Whore
After you’ve climbed every mountain, spend a leisurely afternoon at a local coffee shop, where no one would dream of serving you in a paper cup. In West Stockbridge, try out Six Depot Roastery and Café, which is situated in an old train station and was recently voted the best coffee shop in New England by Yankee Magazine. Around the corner, you could sip on a beverage of choice in front of the fireplace at Shaker Dam Coffeehouse. Adjacent is the gallery of photographer John Stanmeyer.
The Berkshires’ autumnal experience is all about the apples, and none are better than those at Bartlett’s Orchards. Here you’ll find fresh-baked apple cider donuts made with fresh-squeezed apple cider — served piping hot or cooled — along with as many apple varieties as you can imagine ready for purchase at the orchard’s shop or to handpick directly from the orchards. Visit during full moon for a family-style dinner served in the gardens.
If by evening you need to bite on a different kind of fruit, you’ll find a fine selection of the LGBT variety at Rumpy’s Tavern in Lenox, a popular late-night spot. The rainbow sticker on the door’s corner is hardly noticeable, but trust me, you’ll feel at home.
In the Berkshires, you can skip the table and head directly to the farm for a fresh, organic and sophisticated meal. For a guide to all things local, pick up a copy of Edible Berkshires, a free magazine available at local co-ops and Guido’s Fresh Marketplace. For the full table experience, try elegant organic fare in a rural environment at John Andrews Farmhouse Restaurant in Great Barrington. It was voted one of the World’s 25 Best Farmstead Experiences by The Daily Meal. In downtown you’ll also find the super cool Allium Restaurant + Bar, as well as casual Haven Cafe & Bakery, which has locations in Great Barrington and Lenox.
For a consummate fusion of flavor and atmosphere that’s on-the-edge, make your way to The Dream Away Lodge in Becket. Once a 1920s speakeasy, it evolved into a 1960s hangout for the likes of Bob Dylan and Joan Baez. Today, the simple yet sophisticated cuisine made by chef Amy Loveless is often served alongside a hootenanny or the occasional gender-bending cabaret entertainer.
The Culture Vulture
Although summertime in the Berkshires is synonymous with performing arts festivals, fall is peak time for museum visits, when architecture and vistas seamlessly integrate with your tour. The north Berkshires boast two nationally acclaimed art museums. In Williamstown, the stunning Clark Art Institute — also known as The Clark — is known for its impressive collection of French Impressionists. The museum is situated on 140 acres of sprawling meadows and intricate hiking trails, with captivating views of Vermont’s Green Mountains.
Nearby, North Adams is home to MASS MoCa, a world-famous contemporary visual art and performing arts center, located in a converted factory building complex. Be sure to check out their ongoing events, which could range from an outdoor silent film festival or a world music dance party to an avant-garde theater performance.
For a more classic cultural affair, tour The Mount, Edith Wharton’s sprawling turn-of-the century residence and gardens. Located in Lenox, it is a hub of literary and cultural events that include readings with world-famous writers and concerts held on the porch and lawns. A storybook setting for a dreamy wedding, it’s one of only five national landmarks dedicated to women.
Day Trippers, Hipsters and Lady Lovers
Approximately an hour east, Northampton, Mass. in the Pioneer Valley is home to the largest lesbian population, per capita, in the country. The crosswalks are rainbow colored, the bathrooms are unisex and nobody will blink twice at your blended family. Spend the day downtown counting couples and window shopping at the artsy and funky stores. In the evening head to Tunnel Bar, Pearl Street Nightclub or The Deuce, which showcases Bon Appétit, a “women-friendly, body-positive” neo-burlesque show.
Just west of the Berkshires is Hudson, New York, a small Brooklynesque river town that’s brimming with hipsters and weekending New Yorkers. The mile-long Warren Street and its environs overflow with antique shops, vintage clothing stores and artsy cafés. After hours, you might find the likes of Andrea Gibson performing at Club Helsinki or John Waters putting on a one-man show at Basilica Hudson.
It’s well worth the ride to these outlying areas. While Miami rush hour traffic might yield a five-mile crawl down Kendall Drive, in the Berkshires, cruising open roads with unending twists, dips and bends makes autumnal journeys as colorful as the end destinations.
Jacob’s Pillow Festival: jacobspillow.org
Berkshire Theatre Festival: berkshiretheatregroup.org
Tanglewood Music Festival: bu.edu/cfa/tanglewood