A Perfect Fall Weekend in the Berkshires

A mountain destination resplendent with culture, scenery, and eclectic hotels, the area of Western Massachusetts known as the Berkshires is particularly lovely in the fall, with foliage reaching peak in mid-October. While it’s a well-known, well-loved weekend escape for residents of New York and Boston, the rural region feels a bit more off the beaten path to many who live in other parts of the country—but that's beginning to change, and for good reason.

Comprising 30 towns and two cities, North Adams and Pittsfield, the Berkshires region started to develop during the Gilded Age in the late 19th century, when industrialists began to leave New York City to build their mansions in the Berkshire Mountains, about 150 miles to the north. Famous writers, such as Edith Wharton and Herman Melville, followed. When the Boston Symphony Orchestra opened Tanglewood in the town of Lenox some 85 years ago, it unofficially put the Berkshires on the map. Then modern dance pioneer Ted Shawn founded what would become the acclaimed Jacob’s Pillow Dance Festival, solidifying the region’s future as a cultural mecca.

The Berkshires are easily accessible from Hartford, Albany, and Boston airports, all within a scenic few hours’ drive. When it comes to packing, leave your suits and stilettos at home; comfortable shoes do double duty for museum tours and hiking. Get ready for adventure, because you’ve got a lot of ground to cover.

SEE

Welcoming world-class musicians for decades, Tanglewood is one of the centerpieces of The Berkshires. While the time to catch a performance is during the Boston Symphony Orchestra’s eight-week summer residency (July–August) or popular artist concerts (June and September), the stunning grounds are open for the public to enjoy year-round. Pack a picnic (or order one from Nejaime’s Wine Cellars in Lenox or Stockbridge) and have the place nearly to yourself in the fall, surrounded by heritage trees and with sweeping views of Stockbridge Bowl.

Reserve an afternoon for exploring the Mount, the former home of Edith Wharton, just down the road from Tanglewood. An American author who penned more than 40 books in 40 years, Wharton was an authority on architecture, gardens, interior design, and travel, and the first woman to be awarded the Pulitzer Prize for fiction. Visitors to the Mount are invited to interact with the eclectic rooms—especially thrilling during Friday Night Fright, where the most haunted parts of the estate are on full display during two-hour ghost tours running September through October.

A juxtaposition of pastoral landscape (cows roam the pastures surrounding the buildings) with world-class paintings at the Clark makes this art institute truly one of a kind. Home to 30 works by Renoir, the Williamstown museum is known for its European works, primarily French, as well as some notable American paintings. The original white-marble building opened in 1955, followed by a red granite Brutalist building in the ’70s. Both retain their original charm, yet more recently, the museum opened two smaller buildings designed by Todeo Ando. A beautiful reflecting pool and adjacent outdoor terrace, added in 2015, are prime spots for leaf peeping and contemplating the works you’ve seen inside.

The Norman Rockwell Museum in Stockbridge is home to the world’s largest collection of the artist’s work, along with more than 100,000 items like photos, letters, fan mail, and personal calendars in the museum’s archives. From April through November, you can also tour Rockwell’s last studio—he lived in Stockbridge for the last 25 years of his life, drawing inspiration from the community for many of his later works.

Thanks to an expansion in summer 2017, the Massachusetts Museum of Contemporary Art—better known as MASS MoCA—in North Adams is currently the largest contemporary museum in the country. Its name is synonymous with artists like James Turrell, Sol LeWitt, and Laurie Anderson, who each have long-term exhibition space there. You’ll have to fight the crowds to get up close with their works, but quieter, yet equally as powerful exhibits on display are also worth seeing. Don’t miss Liz Glynn’s largest solo museum show to date, Allison Janae Hamilton’s "Pitch," and Taryn Simon’s A Cold Hole (where participants jump into icy water as visitors watch). After your visit, stop into the taproom at Bright Ideas Brewing on the MASS MoCA campus, where you can sample unique brews like Guava Mangose (or get one to go). Savor every sip, as you won’t be able to find these back home—the company is focused on hyperlocal distribution.

STAY

When a fashion designer and an artist collaborate to open a hotel, you’d expect it to be spectacular. The Inn at Kenmore Hall delivers—and then some. Designed by Frank Muytjens, former head of menswear for J.Crew, and his life partner, artist-entrepreneur Scott Edward Cole, the property opened in August inside a 1792 Georgian-style mansion set on 20 meadowed acres. Rife with preserved neoclassical details, the home has been largely unspoiled over its history, but the restoration preserved everything from the nine fireplaces to the slate roof, marble foundation, and rich millwork. Thoughtful details like Matteo linens, radiant-heated en suite floors, and Aesop bath products up the luxury quotient.

An artful reimagining of the retro roadside motor lodge, Tourists is a boutique hotel that debuted in North Adams this summer. Borrowing from its natural surroundings (it’s situated on Mohawk Trail, the country’s first scenic byway, opened in 1914), the hotel has an eco-conscious design that plays off nostalgia. Expansive rear-facing windows overlook the woodlands, river, and mountains, while the interiors feature high-vaulted ceilings, white-oak planks and giant picture windows with built-in lounge seating perfect for reading. Loom, a restaurant from Cortney Burns (formerly of San Francisco’s Bar Tartine), will open early next year.

Several storied hotels in the region also continue to hold their appeal, however. Bibliophiles should book Hotel on North in downtown Pittsfield for its Library Suite. Tucked away into a corner of a 100-year-old building, the room features 125 bookshelves filled with books donated from the community alongside memorabilia and design pieces. The hotel itself is fashioned from two 19th-century buildings on the National Register of Historic Places. Exposed brick walls, tin ceilings, and decorative columns are only a few of the charming nods to its heritage.

Reminiscent of a scene from Harry Potter, the grand Blantyre is a Relais & Châteaux estate set among 100 acres outside Lenox. Its roots date back to the late 19th century, when the Fitzpatrick family converted the Tudor-style mansion into a luxury resort, restaurant, and spa. After coming under new ownership in 2017 and undergoing a multimillion-dollar transformation, this spring it unveiled the Riverview Cottage, a private one-bedroom space furnished entirely by Serena & Lily.

EAT & DRINK

The Berkshires’ casual dining scene can be traced to the original farm-to-table movement. During the Gilded Age, many mansions had working farms that shipped produce back to New York before it became common practice. The region’s Indian Line Farm was also among the first in the country to introduce a CSA program.

Today’s restaurants remain rooted in the tradition of highly seasonal menus and utilizing what’s in their backyard. Mezze Bistro + Bar, which opened in Williamstown in 2010, creates a sense of “food as culture,” with seasonal menu staples like hen-of-the-wood mushrooms with spring parsnip puree, and New Bedford scallops with native corn, leeks, and chanterelles. The kitchen team keeps sustainability top of mind, engaging in activities like foraging and embracing the nose-to-tail philosophy. Be sure to stroll among the property’s edible landscape designs, such as a native stone pathway lined with kiwi, juneberry, lingonberry, cranberry, huckleberry and alpine strawberry plants.

DreamAway Lodge has memorable food, like its famous mac and cheese, but the ambience is what draws people in to this eclectic restaurant in Becket that’s nearly impossible to find unless you ask a local. Mismatched chairs, cutlery, and china add to the appeal of this funky spot that’s literally in the middle of the woods. And if you want to take home an edible memory of your trip, snag a few loaves of sourdough from Berkshire Mountain Bakery—the best bread around.

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