Summer often seems in short supply in New England. But when it’s available, locals and visitors alike know they’ve got to strike while the weather is hot. The period from June to September proves especially perfect to appreciate the Berkshires, the bucolic, mountainous region in Massachusetts’s westernmost stretches, a three-hour drive from New York City or Boston. In summer, the area’s many natural wonders meet their match in cultural offerings, from symphony concerts to dance festivals to art exhibits. Here’s our guide to making the most of a weekend visit.
The longtime warm-weather and largely alfresco home of the Boston Symphony Orchestra, Tanglewood will celebrate its 82nd season of music in the Berkshires—running from June 15 through Labor Day—with the launch of the Tanglewood Learning Institute (TLI). The new programming will bring fans closer than ever to artists and creators through performances, master classes, speakers, and workshops, all of which will take place across four new structures—the biggest building project on the 529-acre campus in 25 years. Beyond TLI, 2019 season highlights include Wagner’s Die Walküre with Stephanie Blythe and the debut of new work by Pulitzer Prize–winning composer Kevin Puts featuring Renée Fleming. More interested in pop? Check out Pat Benatar, the Goo Goo Dolls, Ben Harper, Gladys Knight, Reba McEntire, and James Taylor.
Other places to get your performing arts fix in the Berkshires include Jacob’s Pillow, a seasonal dance festival of shows, classes, talks, and exhibitions in Becket, and the Williamstown Theatre Festival, which has presented new and classic plays with big-name and on-the-rise talent every summer since 1955.
On the outdoor-adventure side of things, the Berkshires offers hiking, biking, canoeing, and kayaking to spare. Western Massachusetts is home to 90 miles of the Appalachian Trail, including pathways over Mount Greylock, the state’s highest point. The summit, which you can also access by car, features a 12,500-acre preserve, plus the 1930s Bascom Lodge for lunch, drinks, and even overnights.
The paved, 11.2-mile Ashuwillticook Rail Trail, meanwhile, follows the path of an old train line from Lanesborough to North Adams, providing views of the mountains, the Cheshire Reservoir, and the Hoosic River. There’s also the Cascades Trail, which makes for a fairly gentle walk close to downtown North Adams—with the payoff of a refreshing waterfall.
Two of the coolest spots to spend the night in the Berkshires are also among the newest. In North Adams, near MASS MoCA, Tourists opened in summer 2018, after a group of creatives, including the bassist from the band Wilco, turned a midcentury motor lodge into a contemporary, rustic-chic hotel. Its bar and comfort-food joint, Airport Rooms, landed this spring in a once-derelict 1813 farmhouse on the 55-acre property. Closer to Lenox and Tanglewood, The Inn at Kenmore Hall comes courtesy of J. Crew’s former head of menswear, Frank Muytjens, and chef and artist Scott Edward Cole. The pair turned a 1792 Georgian estate into a five-room, home-like hotel, with an adjacent carriage-house guest cottage. The whole place combines 18th-century bones and contemporary style.
In Lenox proper are two of the Berkshires’ most storied stays, both in gilded age mansions. Thanks to its new owner, the Tudor-style Blantyre—the first Relais & Châteaux property in the United States—recently received a top-to-bottom renovation. It sits on 110 acres of lawns and woodlands, with eight rooms, 11 suites, and four cottages all classically, but never fussily, done in antiques and earth tones. Bonuses of the redo include an enhanced spa and new Dom Pérignon tasting room. Then there’s Wheatleigh, which occupies an 1893 country house based on a 16th-century Florentine palazzo. Here, the 19 rooms and suites overlook 22 acres of gardens designed by Frederick Law Olmsted, who famously created New York’s Central Park.
Several chefs with New York pedigrees have left the city to set up shop in the Berkshires with great success. Among the most buzzed about is Mark Frist, who made his name at Brooklyn’s Diner and Marlow & Sons. At the Prairie Whale, in a Greek revival house on Great Barrington’s Main Street, he turns out an ever-changing menu of sustainable, farm-to-table fare.
Another is Joshua Needleman, who worked at La Maison du Chocolat in Manhattan before opening Chocolate Springs Café. At the Lenox favorite, he makes must-try cakes, cookies, and gelato and laces his chocolate confections with flavors like kalamansi, lavender honey, and rose tea.
Multi-time James Beard Award nominee Bjorn Somlo, a Berkshires native who also spent time in New York, launched Nudel in Lenox in 2009; he works with top regional farms to create seasonal American fare. In his cozy, modern space, you can eat at several by-reservation tables or, better yet, at a walk-in-only chef’s counter with kitchen views.
Following in Somlo’s footsteps, Nudel alum Josh Irwin runs Cantina 229 with his wife, Emily, on farm-like land in New Marlborough. Here, guests enjoy wallet-friendly, globally inflected American cuisine in several different settings, at either communal or private tables both indoors and out. The taco Tuesdays are a particular favorite.
For something classic, try Mezze, set on three pastoral acres in Williamstown. Inspired by the Greek-Moroccan background of owner Nancy Thomas, the restaurant serves farm-to-table bistro fare with Mediterranean flair. Over the course of more than 20 years, it has won rave reviews for dishes like roasted carrot hummus and herb-roasted chicken roulade.
A Berkshires getaway can include both rustic and sophisticated pleasures—listening to symphonic orchestras and shopping farm stands, hiking rail trails and viewing avant-garde artwork at MASS MoCA. The most challenging part of enjoying the region is finding the time to do and see everything.
>>Next: See AFAR’s Other Picks for Where to Go in 2019