Ever since I can remember, I've been going up to the Berkshires with my family. The region, located in western Massachusetts, is gorgeous year-round, but it particularly shines in the warmer months. Summer in the Berkshires is near and dear to my heart: It's where my sister and I went to sleepaway camp, where my husband and I got engaged, and where I've spent countless nights sitting with my grandparents on their patio, taking in the sunset over the lake and talking about nothing and everything. If you're looking to explore the Berkshires for a weekend this summer, here's everything you need to know. (With input from my grandmother, Carole, who knows more about the cultural life of the Berkshires than any self-proclaimed travel expert out there. Trust me.)
The Performing Arts
There's no shortage of world-class performances in the Berkshires, and no trip is complete without a night at Tanglewood, the summer home of the Boston Symphony Orchestra, where offerings range from James Taylor on the Fourth of July (a must) to musicians such as Judy Collins, the Indigo Girls, and Rufus Wainwright, and the ever-popular John Williams' Film Night. Plus, Barrington Stage is celebrating its 30th anniversary this year, with productions of La Cage Aux Folles and Next to Normal on their lineup. Or, for more theater, check out the Mahaiwe Performing Arts Center's schedule. The historic stage, which was built back in 1905, is home to the annual Berkshires Opera Festival, and also hosts screenings of old films, and acts by comedians such as Patton Oswalt.
If an evening at the ballet is more your taste, taking in a performance at Jacob's Pillow is an experience absolutely not to be missed. "The Pillow is one of the most glorious places to experience dance," Pamela Tatge, Executive & Artistic Director of Jacob's Pillow, tells T&C. "Visitors can not only experience the performances outdoors against the backdrop of the Berkshire hills, or indoors in the first theater created in the United States specifically for dance, but they can also view exhibitions, participate in classes and workshops, and attend talks that contextualize the work that they're gonna see." This summer, Tatge is particularly looking forward to the Royal Ballet's engagement, as the famed British company makes its Pillow debut.
Museums
If your itinerary allows, plan to spend a whole day at The Massachusetts Museum of Contemporary Art (Mass MoCa) in North Adams, one of the largest modern art museums in the world. Be sure to check out the Sol LeWitt wall drawing retrospective, and Spencer Finch's "Cosmic Latte" installation, but also leave time to simply wander the acres of galleries.
Literary lovers should stop by Edith Wharton's home, The Mount, a historic house museum with gorgeous grounds and a full slate of summer programming, including a schedule of lectures (featuring Peter Hessler, Safiya Sinclair, and Jonathan Eig, among other writers) and its popular "Wharton on Wednesday" series, during which local Berkshires actors bring Wharton's short stories to life. "It doesn't feel like a house museum at all, because we have no velvet ropes. Visitors can walk the property, and explore the house, at their own tempo, and really feel as if they're a guest in her home," Susan Wissler, the executive director of The Mount, tells T&C. "
In addition to the Wharton-focused offerings, the estate features beautiful gardens and woodlands. The property is open from dawn to dusk every day as a public park, and this summer marks their 10th annual sculpture show. "I come to this campus every day and you're transported because you enter the grounds and you're in another world," The Mount's Director of Programs, Sarah Margolis-Pineo, says. "It's cooler, the air is fresher. It's just outstandingly beautiful. There's always something surprising and new to notice. Wharton was so deliberate in how she sort of choreographed your entrance and your encounter with her estate—going through the fields and forests and woodlands and and streams and the progression to the house. One of my favorite aspects of working here is enjoying the terrace in the back of the house—you have a gorgeous vista of the Berkshire Hills, and you can enjoy a really lovely lunch with an iced tea or a glass of wine and just take it all in. It's otherworldly—it's really an embodiment of summer in so many ways."
Other local museums worth perusing include the Norman Rockwell Museum in Stockbridge, which hosts the largest and most significant collection of Rockwell's work (including over over 300 of his Saturday Evening Post covers), and the Clark Art Institute in Williamstown, which offers an impressive French Impressionist collection, and an incredible reflecting pool.
If you're traveling with kids, the Berkshire Museum in Pittsfield makes for a fun afternoon. It's worth a visit for the aquarium on the first floor alone, but also features numerous interactive exhibits focused on natural history, science, and art.
Plus, history buffs should visit Hancock Shaker Village, a living history museum with 20 historic Shaker buildings that visitors can explore to understand Shaker daily life. The Village also has a herb gardens, heirloom vegetable gardens, heritage livestock, and a working farm dating back to 1783—impressively, the farm is still using sustainable Shaker farming methods to this day.
The great outdoors
Prioritizing spending time outdoors is a given when visiting the Berkshires in the summer. Pick-your-own blueberries season just started at Windy Hill Farm. My husband's tip: Go farther back to get to the less-picked-over trees. Keep walking for the best selection!
An easy hike can be found at Monument Mountain, a 3.8 mile out-and-back trail near Great Barrington with a great view, or if you're looking for something less strenuous, my sister and her friends love to explore the beaver ponds at Pleasant Valley Wildlife Sanctuary (run by the Mass Audubon Society). The best view (with no hike required), can be found by driving to the peak of Mount Greylock (near Adams), the highest point in Massachusetts where, on a clear day, you can see for miles. (There is also an option to do the 5.5 mile out-and-back hike up Greylock.) The best bike path—for biking, running, or just walking—is undoubtedly the Ashuwillticook Rail Trail, which runs from Pittsfield to Adams.
For families, kid-friendly outdoor activities aren't hard to come by. The Jiminy Peak ski resort (in Hancock), is a favorite of thrill seekers in the summer—its Mountain Adventure Park offers an alpine slide and a mountain coaster. Catamount (in South Egremont), too, will appeal to those lacking a fear of heights, with its zipline and ropes course. And, on hot days, there are a surprising number of waterfalls to explore in the Berkshires—Bash Bish Falls is a bit of a drive in Mount Washington, but worth the detour, or go local and swim at Umpachene Falls Park in New Marlborough.
Where to stay
For a historic hotel with easy access to the entire region, the Red Lion Inn, in Stockbridge, is a great choice. "At the Red Lion Inn, we cherish the long, warm days filled with guests relaxing on our porch," Sarah Eustis, the Founder and CEO of Main Street Hospitality (owners of the Red Lion), tells T&C. The property has been around for over two centuries, but it doesn't feel dated, and features 82 rooms and suites in its main building, plus unique, romantic guest houses if you're looking for more privacy. Also of note: an on-property speakeasy featuring live music and cocktails Wednesday to Sunday.
For a wellness-focused getaway, stay at Canyon Ranch in Lenox, and spend as much time as possible at their spa (or participating in daily activities such as hiking, pilates, and pickleball), or book a yoga retreat at Kirpalu in nearby Stockbridge. Other bucolic accommodations include the rustic-yet-contemporary Gedney Farm in New Marlborough, which features 16 guest rooms in a converted barn; Blantyre in Lenox, a Gilded Age house-turned-luxurious hotel, which is currently closed, but reopening later this year after a renovation; the Williams Inn in Williamstown, a modern inn that has 64 guest rooms in a fantastic location (it's near Mass MoCa, the Clark, and Williams College); or the Old Inn on the Green, also in New Marlborough, formerly a stagecoach relay, which now houses a historic inn with restored guest rooms full of charm.
What to eat
The Berkshires food scene has been flourishing in recent years, with new additions like Heirloom Lodge in West Stockbridge, but there are still some tried-and-true dinner spots worth keeping on the itinerary: Baba Louie's pizza in Great Barrington for their thin-crust sourdough pizza; Alta (my grandfather recommends the pork cheeks) or Bistro Zinc in Lenox for a nice dinner out; The Old Inn on the Green in New Marlborough for a special occasion; and Bizen in Great Barrington for the best sushi in the Berkshires. If you're looking for live music with your dinner, head to the recently reopened Dream Away Lodge in Becket.
For lunch, the best sandwiches in the Berkshires, hands down, can be found at Bizalion's Fine Food in Great Barrington; as beauty guru Jane Iredale wrote in T&C in 2015, Bizalion's "is a little bit of Marseilles in the Berkshires. It's a grocery and lunch mecca where you will hear as much French being spoken as English. Lining the walls are tubs of aromatic olive oil, specialty foods (if you want the best truffle paté for miles around, this is the place to get it) and light and crisp baguettes that taste like they are imported from across the Atlantic." I couldn't have put it better!
The best cheese in the Berkshires can be found at High Lawn Farm in Lee, a working dairy farm, complete with cows ready to greet visitors. There, check out a wide range of cheeses (including my favorite, their High Lawn Queen, a soft cow's milk cheese), ice cream, and other dairy products, like cultured butter and cheese curds. Or, go to Cricket Creek Farm in Williamstown, which offers a curated selection of seven artisanal farmstead cheeses.
If you're searching for a sweet treat, the ginger molasses cookies at Taft Farms in Great Barrington cream are the best, bar none. The best ice cream can be found at SoCo Creamery in Great Barrington, and every type of candy imaginable be purchased at the throwback Robin's Candy Store, also in Great Barrington. Marijuana-infused treats—it is Massachusetts, after all—can be picked up at Calyx, the only female-owned dispensary in the Berkshires.
Other key food stops whenever I'm in the Berkshires: coffee from No. Six Roastery and Cafe (West Stockbridge); baked goods from Lost Lamb (Stockbridge) or Patisserie Lenox (in both Lenox and Great Barrington); soup from Farm Country Soup (Great Barrington); and prepared foods can be found at Guido's Fresh Marketplace (in Pittsfield and Great Barrington; honestly, everything there is fantastic).
Last but not least: Berkshires farmers' markets are not to be missed—the best one is in Great Barrington, on Saturday mornings (put 18 Church St. into the GPS), for fresh produce, meats, baked goods, flowers, and so much more.
Emily Burack (she/her) is the Senior News Editor for Town & Country, where she covers entertainment, culture, the royals, and a range of other subjects. Before joining T&C, she was the deputy managing editor at Hey Alma, a Jewish culture site. Follow her @emburack on Twitter and Instagram.
