Itinerary: Berkshires

A historic playground for artists and Gilded-Age elite endures as an idyllic Northeast cultural hub.

Of all the old and special places in North America, the Berkshires region of western Massachusetts was among the first to be considered as such. Settled in significant numbers only after the French and Indian War, the area became a magnet for writers and artists less than a century later.

Herman Melville moved to Arrowhead, the Pittsfield farmhouse where he would write Moby-Dick, in 1850. Chesterwood, established during the 1890s and now a site of the National Trust for Historic Preservation, was the home and studio of the sculptor Daniel Chester French, who created the statue of Abraham Lincoln for the Lincoln Memorial. By 1902, when Edith Wharton built her influential Lenox estate, The Mount, wealthy New Yorkers and Bostonians were dotting the landscape with opulent Gilded Age “cottages.” Both groups were drawn to the beauty of the Berkshire Mountains, and to a small-town New England life that Norman Rockwell -- a Stockbridge resident -- would later enshrine as an American archetype.

The region had its industrial heyday -- witness the 19th-century mills of Great Barrington and North Adams -- but its dominant image remains one of scenic rolling hills and picturesque villages infused with a dose of urban cultural vitality. The Boston Symphony Orchestra makes its summer home at Tanglewood, in Lenox and Stockbridge, as it has since 1937. The Becket campus of Jacob’s Pillow, the country’s preeminent summer dance festival, is now a National Historic Landmark.

But the Berkshires arts scene runs as broad and deep as the area’s range of preserved historic buildings, opportunities for outdoor recreation, and outstanding inns and restaurants. To narrow down the list, Preservation drew on the experience of three longtime Berkshires residents:

  • Ed Locke, maintenance contractor and landscaper. A fourth-generation Berkshires native, Locke was a child model for two of Norman Rockwell’s Saturday Evening Post covers: “The Runaway” and “Before the Shot,” both in 1958.
  • Robert Salerno, president of the West Stockbridge Historical Society. Salerno commutes once a week to New York City, where he teaches retail management at the Fashion Institute of Technology.
  • Diane Pearlman, independent film producer and executive director of the Berkshire Film and Media Commission. Pearlman was visual effects executive producer at Mass.Illusions, the studio that created visual effects for The Matrix.


For Locke, a good day starts with breakfast at Martin’s, in Great Barrington, a plain-wrapper local treasure that has specialized in fresh, locally grown food since it opened in 1989. “It’s very busy on the weekends,” Locke says, “but for my money, they have the best eggs Benedict in the world.”

Baba Louie’s, in Pittsfield and Great Barrington as well as Hudson, N.Y., turns out all-natural, sourdough wood-fired works of art. “It’s upscale pizza,” Pearlman says, “but you can take your family there.” The Old Inn on the Green, in New Marlborough, offers sophisticated New England fare in a setting that is both historic and romantic. “There’s no electricity,” Pearlman says. “You eat by candlelight.”

For a white-tablecloth night out, Salerno recommends Blantyre, a private estate turned luxury inn in Lenox. “It has great food and accommodations,” he says. “It’s not cheap, but if you want to treat yourself, that’s the place to go.”

All three of our local experts consider a meal at the Red Lion Inn, a Historic Hotel of America (HHA), in Stockbridge, virtually mandatory. “It’s a classic Berkshire country inn,” Salerno says. The Red Lion serves regional specialties in its formal New England dining room, rustic tavern, pub, and outdoor courtyard.


If Stockbridge is the heart of the Berkshires, the Red Lion Inn is the heart of Stockbridge. “It’s been a fixture since before my grandparents were around,” Locke says. In fact, Salerno notes, “it was an old stagecoach stop in the 1700s.” The interior of this HHA features guest rooms each with unique decor, but Salerno has a special appreciation for the wide front porch. “Put me there in a rocking chair,” he says, “and I’m set for the day.”

Pearlman enjoys occasional weekend getaways at Cranwell, an HHA in Lenox. “It’s lovely because it’s an all-around resort,” she says. “You can play golf; they have a lovely spa; and if you get a room in the old mansion, well, you’re in a beautiful old mansion.”

The Kemble Inn, an 1886 Colonial Revival cottage in Lenox, is another favorite. “[Owner] Scott Shortt has done a great job of renovating it,” Pearlman says.
Part of the post-industrial revival of North Adams spurred by the Massachusetts Museum of Contemporary Art, The Porches Inn (also an HHA) links a block of Victorian row houses into a single, innovative hostelry. “It’s great for people who are going to MASS MoCA,” Pearlman says. “The rooms are simple but elegant.”

For a casual and affordable vacation rental, Salerno often sends out-of-town visitors to 31 Stockbridge Road in West Stockbridge. “The people who run it are so friendly,” he says. “It’s kind of like having your own farmhouse.”


“For me, in the summer it’s Jacob’s Pillow and Tanglewood,” Pearlman says. “I love going to Inside/ Out,” a series of free outdoor dance performances that runs at Jacob’s Pillow from mid-June through August. To stretch one’s own legs, she recommends hiking on Great Barrington’s Monument Mountain or cycling the 11.2 mile Ashuwillticook Rail Trail. “It goes from Lanesborough all the way to Adams,” says Pearlman. MASS MoCA, just six miles away in North Adams, she considers “a must.”

Salerno’s recommendations begin with a trio of historic homes: Naumkeag, a 44-room McKim, Mead & White country estate with “wonderful restored grounds” in Stockbridge; Ventfort Hall, in Lenox, a Jacobean Revival brick mansion, now a museum, that was built for J.P. Morgan’s sister Sarah; and -- “absolutely” -- Edith Wharton’s The Mount. Salerno also enjoys live theater at the Barrington Stage Company, in Pittsfield, the Berkshire Theatre Festival, in Stockbridge, and Williamstown Theatre Festival. The Mahaiwe Performing Arts Center, in Great Barrington, also merits a visit, he says. “It’s a restored 1905 theater. It’s a great place for people interested in preservation.”

Locke’s picks include a tour of the Ashley House, the 18th-century Sheffield home of Colonel John Ashley. “Elizabeth Freeman -- ‘Mum Bett’ -- was his slave. She petitioned to be set free and won her freedom in court,” Locke says.

“The Berkshire Botanical Garden, in Stockbridge, is also a wonderful place. And I would be remiss if I didn’t mention the Norman Rockwell Museum [also in Stockbridge]. Make sure to pay special attention to those two particular Saturday Evening Post covers … ”

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