Scenes from the Berkshires: plates of food on the table at Cantina 229; view from a hotel room onto an autumn landscape

Discover Foliage, Farm-to-Table Dinners, and World-Class Museums in the Berkshires

When the summer crowds pack up, the Berkshires turn into one of New England's most beautiful weekend escapes.

Years ago, I would take the bus from Boston, where I went to college, to visit my parents back home in upstate New York. I came to know the journey by heart. The coach would lumber along the turnpike to the western end of Massachusetts, then follow a poky local route through the low-lying Berkshire mountains.

The landscape was beautiful—especially in autumn, when the trees were on fire—and the more popular tourist towns looked like they hadn't changed much since the 1970s, when James Taylor name-checked the Berkshires in "Sweet Baby James." When my bus stopped in Lenox, home to the outdoor classical music venue Tanglewood, I would watch a khaki-and-loafers crowd mill about streets lined with quaint boutiques. But a forlorn, dusty aura hung over other parts of the region; the larger cities, North Adams and Pittsfield, were former manufacturing hubs that had clearly fallen on hard times.

Many decades later, my husband and I sat on the patio at Tourists, a reimagining of the archetypal American motel built on the site of an old motor lodge halfway between Williamstown and downtown North Adams. We took in the crowd around us: a guy with a New Order T-shirt, a gay couple with a big white dog, a stylish man and woman in their eighties. The scent of burning wood filled the air. I heard a train pass in the distance. Caleb's beer came in a can designed with the same font and color palette as the Beach Boys' Pet Sounds album.

Then a server spread an entire garden before us: sweet and spicy hummus with marinated vegetables and a sheet of naan the size of an elephant's ear; crispy quinoa and freekeh tossed in a creamy kefir dressing and topped with avocado and jack cheese; a salad of fire-alarm-red tomatoes. Moments before, I had overheard a man at another table going on about how "fresh" the food was. Yeah, yeah, I thought. Everything's "fresh" these days. But this was picked-five-minutes-ago fresh. Watching the sky above the lodge's peaked roof turn a smoky purple, I mopped up the last of the hummus and felt a tingling sense of delight.

Scenes from the Berkshires: the Hoosic River in autumn
The Hoosic River flows through the grounds of Tourists, a hotel in North Adams, Massachusetts. | Credit: Nicole Franzen

From Route 2, the commercial strip out front, Tourists looks like a series of wood-sided hangars. (I later learned that the Modernist architecture of Sea Ranch, California, was a primary inspiration.) But a more rustic scene unfolds around back, where Caleb and I explored a 30-acre swath of woodland through which the trout-stocked Hoosic River flows. Each guest room has a large window that frames this thickly green landscape and a rear terrace from where the busy main road seems worlds away. A footpath leads across an impressive suspension bridge, then winds around the property, passing industrial relics and, at one point, intersecting with the Appalachian Trail.

The rooms have a camplike sparseness, with white walls and plywood furniture. But the roughing-it atmosphere is offset by a number of thoughtful details: a window seat about the size of a twin bed; a trio of soaps laid out on a board like cheeses. An arrangement of vintage snapshots above our desk nodded to the region's history as a vacation mecca during the rise of automobile tourism in the early 20th century. Co-owner John Stirratt, the bassist for the band Wilco, programs Tourists Radio, which can be played on each room's retro-looking receiver. The station is also streamed in the main lodge, where the next morning we listened to Townes Van Zandt and Big Thief while I ate an egg sandwich that brought me to the realization that egg sandwiches are my all-time favorite food.

The new, more youthful Berkshires that Tourists has come to represent is the result of what Ben Svenson, another of the hotel's co-owners, described to me as "re-pioneering." He defines the term as "people from outside looking at a place with a fresh set of eyes, loving the history of it and wanting to respect it, but also imagining a different future for it." Tourists, says Svenson, is "a disciple of Mass MoCA," the contemporary-art museum three miles east in downtown North Adams. (In fact, the hotel guest rooms are the same shade of white as the gallery's walls.) The opening of the museum in 1999 in an abandoned electric works arguably jump-started the northern Berkshires revival. Over the ensuing decades, Mass MoCA has developed into its own sprawling universe, as more of the dilapidated buildings have been transformed into exhibition spaces.

"I love the feeling of a bunch of stuff around me," I overheard a teenage girl say as Caleb and I walked through the galleries the next morning. Mass MoCA overwhelms. Everything is oversize, or superabundant, or subsuming. A Jarvis Rockwell installation is made up of towering shelves of dolls and vitrines filled with vintage board games and toy figurines. A shower of LEDs, arranged by Spencer Finch in the form of the Milky Way, descends from the ceiling of a brick-lined hallway. Enter a windowless, capsule-shaped room designed by James Turrell and you're bathed in a sequence of gently shifting colors.

Mass MoCA has strong ties to the music world, in part due to its close relationship with Wilco: the band curates and performs at a biannual festival held at the museum called Solid Sound, inviting along such friends as Courtney Barnett and Cate Le Bon. These alt-rock connections spill over into the galleries. We toured an exhibition of paintings by Chrissie Hynde and an installation by Annie Lennox, who half-buried a number of her possessions—tarot cards, cassettes, a piano, her gold record for "Sweet Dreams Are Made of This"—in an enormous pile of dirt.

Scenes from the Berkshires: interior of a gallery with paintings at the Clark Institute
One of the Clark Art Institute’s galleries of European paintings. | Credit: Nicole Franzen

Three miles west of Tourists, the Clark Art Institute delivers what feels like the opposite of Mass MoCA's funhouse atmosphere—and yet it's every bit as transcendent. Caleb and I have a long history with the museum. We discovered it when we were in our thirties: a day trip there was a rewarding way to spend an afternoon with my parents when we would drive up from Brooklyn to visit them. My mother and father relished seeing works by the painters they loved: Monet, Morisot, Pissarro, Sargent, Degas. The museum was built in the 1950s, when an heir to the Singer sewing machine fortune, Robert Sterling Clark, and his wife, Francine, wanted to protect their personal collection from the possibility of a nuclear attack on New York City and decided that pastoral Williamstown was a safe enough site.

A massive expansion, completed in 2014, has turned the Clark from a somewhat sleepy estate into a buzzing tourist draw. Thanks to a subtle overhaul, the original galleries are warmer and friendlier, with a special room devoted to my favorite Clark discovery, the 19th-century landscape painter George Inness. The main building is almost overshadowed by Japanese architect Tadao Ando's new wing, which holds multiple spaces for temporary exhibitions and hugs a vast reflecting pool.

The Clark has 120 acres that fan out from the museum, with meadows scored by walking trails. We were tempted to explore them, but I had arranged another way for us to experience the bucolic side of the Berkshires. Ramblewild, 12 miles to the south, bills itself as a "tree-to-tree adventure park." "I'm not going to tell you anything about it," I told Caleb. "I'll just let it be a surprise." The truth is I wasn't so sure what it was myself.

From the lodge at Ramblewild's entrance, we were driven deep into the forest, then outfitted in helmets and harnesses like Wichita linemen, and led to a hemlock grove, where a vast complex of rope ladders, tunnels, ziplines, swinging wooden steps, and balancing wires has been constructed high in the trees. From a central platform, eight trails lead in different directions, each with a variety of obstacles and levels of difficulty. We climbed, swung, crawled, shimmied. We were clamped onto guide cables, so I never felt afraid. Indeed, how could I look down, when all of my wits were concentrated on overcoming the next challenge? I may have never felt so far from my everyday worries.

Scenes from the Berkshires: an aerial obstacle course in the woods at Ramblewild, and a hanging light art installation at Mass MoCA
From left: Aerial obstacle courses at Ramblewild; Cosmic Latte, an installation of suspended LEDs by Spencer Finch, at Mass MoCA. | Credit: Nicole Franzen

We completed two or three moderately challenging courses, and I said to myself, I've got this. Then we came to the end of the Flying High Trail: a pedestal 45 feet off the ground. I looked around. No steps back to the forest floor, nothing but empty space underneath us. The only way down was to hook myself onto a retractable pulley and jump, as though skydiving. The 12-year-old behind us offered to demonstrate—"I've done this a bunch of times," he explained before clamping himself to the pulley and flinging himself backward. Caleb went next, shouting an obscenity into the sylvan glade. Then it was my turn. I think I actually cried a little, but after a moment's free fall, the pulley clicked into action and delivered me to the ground as softly as a feather.

We were pleasantly exhausted by the time we arrived at the Inn at Kenmore Hall. A Revolutionary War soldier built the house in 1792; nearly a century later it became a boarding school, and later still a guesthouse popular with composers and musicians visiting Tanglewood, including Leonard Bernstein. In 2018, Frank Muytjens, previously the menswear director of J. Crew, and his partner, Scott Edward Cole, a former restaurateur, reopened the property as a bed-and-breakfast. Stripping away the grannyish décor associated with the genre, they've created a 21st-century version of a New England inn— less Yankee, more Architectural Digest.

Our second-floor room was painted a dark, calming gray that matched a plush sofa, and was furnished with a white marble fireplace, a Finn Juhl chair that Caleb was so taken with he started pricing it online, and a pile of art books that included Fairfield Porter, Herb Ritts, and Edward Weston.

Our bathroom was Goth-chic: black walls, candles, and antique mirrors, with a deep tub in the center. The windows overlooked the sweeping lawns behind the house, where every so often I would spot Dutch, the affectionate resident Vizsla, loping around. The inn stands at a quiet intersection in the middle of tranquil farmland—there's not much immediately nearby, but no other part of the Berkshires is very far away.

Muytjens recommended two restaurants in New Marlborough, a small village a 45-minute drive away, and Caleb and I visited them on consecutive nights. The clapboard building that houses the Old Inn on the Green has been around since the mid 18th century, and the dining room looks uncannily frozen in time. (Caleb remarked that it was like being allowed to eat dinner in one of the period rooms at the Met.) The floorboards creak, the Windsor chairs encourage good posture, and the tables are lit solely by candlelight. The cuisine is classic American with a French slant: pan-roasted halibut, cauliflower soup, pot de crème, all excellent.

The next evening, we found a very different scene just a fraction of a mile down the road. Cantina 229 is a farm-to-table restaurant where the farm is directly beneath your feet. After parking in a clearing and walking through a meadow of wild raspberries and morning glories, past some chickens and ducks having an evening amble behind the farmhouse where owners Josh and Emily Irwin live with their family, we came to the restaurant, a modern wood-and-glass pavilion. There we were seated on a broad open-air deck overlooking the surrounding fields. The atmosphere was relaxed and convivial; Roxy Music and the Psychedelic Furs played over the sound system.

Everything that came out of Josh's kitchen was not only deeply flavorful but ingeniously concocted: a fat scallion pancake topped with tangy kimchi; a ball of burrata dolloped with pesto and served over toasted carrots; tender scallops in a curry cream sauce; a spicy vegetable pasta. I'm the kind of person who can enjoy every bite of a meal but is still secretly just waiting for dessert, and I was rewarded with the best ice cream I've ever tasted. Cantina 229 makes its own soft serve, and on that night, the featured flavors were cinnamon toast crunch, a strikingly accurate homage to the breakfast cereal, and chocolate infused with mint straight from the garden. I finished my meal content in stomach and soul.

Josh's goals are humble. "Cantina to us is just a watering hole," he told me. "It's a meeting place for our people here in New Marlborough, and anybody else who wants to join our little community is more than welcome." I'm convinced that the Irwins' achievement is far greater. With their openhearted sense of fun and a menu that playfully mixes up flavors from different culinary cultures, they've made this quiet corner of the state feel emphatically connected to the rest of the world.

Scenes from the Berkshires: exterior of the Blantyre Hotel and the entry hallway at Kenmore Hall
From left: Blantyre, once a private home modeled after a Scottish Castle, is now a resort; the entry of the Inn at Kenmore Hall, a sophisticated bed-and-breakfast. | Credit: Nicole Franzen

It had turned overcast and misty, fitting weather to check in to Blantyre, a 110-acre estate on the outskirts of Lenox. The Tudor Revival manor at its heart, built in the first years of the 20th century for a single family, was modeled after the clan's ancestral seat in Scotland. The building looks baronial, with ivy-covered turrets and a music room bookended by fireplaces. But the hotel isn't resistant to a bit of whimsy. A wooden statue of a bear hides a Tesla charging station. "And your keys are in the bunny bowl," the porter said after showing us our room, pointing to a brass vide poche in the shape of a rabbit rowing a dinghy.

The hallways are lined with bookshelves, and it took forever to walk to our room because Caleb was always stopping to pick up The Oxford Book of English Verse, or a monograph on Byzantine art in Italy. Blantyre was recently given a thorough renovation, and our room harked back to classical styles of decorating while still feeling fresh and bright.

We ate dinner in the handsome glass conservatory, and as we sat down I was overcome by a feeling of security: the crisp autumn night outside the windows, the warm Parker House rolls, the two couples at the next table recalling their favorite Neil Simon plays.

"This is pure New England," I said.

"No, it's not," Caleb corrected me. "If it were, it would be drafty and austere, and people would be making us feel bad for something we hadn't done."

The town of Lenox has largely withstood any attempts to be too on-trend, as we discovered the next day, when we swung through—the shopping streets looked unchanged since the years when my bus stopped there. We drove on to the two-road town of West Stockbridge, where we fortified ourselves with panini at No. 6 Depot, a deservedly popular café, before tackling Monument Mountain, on the outskirts of Great Barrington. At 1,640 feet, the peak makes for a moderately effortful hike. From the top Caleb and I surveyed the surrounding countryside, blanketed to the horizon in shades of honey and rust. (Herman Melville and Nathaniel Hawthorne first met when they picnicked with some friends there in 1850, which led to one of American literature's great man-crushes.)

Back at Blantyre, I hunched over my phone, scrolling through listings of local restaurants we could try. Finally I gave up pretending. "I really just want to go back to Cantina 229," I said. So we did, and the meal was every bit as good as the previous one.

As we got up to leave, Josh came out of the kitchen to say hello. Overcome, I threw my arms around him in gratitude.

"Was that weird?" I asked Caleb on the way out to the car. "I hugged the chef."

"It's okay," he said. "Sometimes you hug the chef."

Scenes from the Berkshires: two people taking a photo in front of the Veterans War Memorial at Mount Greylock
The Veterans War Memorial Tower on top of Mount Greylock. | Credit: Nicole Franzen

The Best of the Berkshires

Where to Stay

Imagine a Scandinavian summer camp for adults, and it might look like Tourists (doubles from $269). The 48-room motel in North Adams augments its spare but sybaritic rooms with a wooded property to wander.

The five-room Inn at Kenmore Hall (doubles from $375), in Richmond, gives a contemporary update to classic bed-and-breakfast style.

Blantyre (doubles from $645), in Lenox, has the feel of a grand manor. In 2018, a face-lift brightened its 23 rooms, and seasonal pop-ups, like a recent one with chef Daniel Boulud, keep things fresh.

What to See

In addition to a permanent collection that ranges from the fifth century B.C. to the present, the Clark Art Institute ―which reopened this summer after shutting for a few months―hosts intriguing temporary exhibitions; timed-ticket shows on Norwegian visionary painter Nikolai Astrup and the sculptors Claude and François Xavier Lalanne are planned for 2021.

The Massachusetts Museum of Contemporary Art, or MASS MoCA, is housed in a former factory; its size offers space for massive installations as well as social distancing.

Work off the hours you've spent on contemplative museum-going at Ramblewild, an aerial adventure park in Lanesborough. Or take a hike up Monument Mountain, just north of Great Barrington, or Mount Greylock, in Adams.

Where to Eat

Walk into the Old Inn on the Green (entrées $28–$46), in New Marlborough, and you'll feel like you've been transported to the 18th century, but the exquisitely prepared food is of the moment. Just down the road, Cantina 229 (entrées$20–$36), which occupies a glass pavilion on a farm, is casual, friendly, and delightful, with a menu that highlights Josh Irwin's inventive blend of global flavors.

No. 6 Depot, in West Stockbridge, serves excellent sandwiches and coffee.

A version of this story first appeared in the November 2020 issue of Travel + Leisure under the headline An Autumn Sonata. Visit berkshires.org for more information.