Berkshires in Winter? How This East Coast Summer Spot Has Become a Off-Season Fave


Scenic and snowy Berkshires (Kimberly Egan/Visit the Berkshires Facebook)

The Berkshires in western Massachusetts have long been a favorite summer playground, and for good reason: The area is home to Tanglewood, the summer home of the Boston Symphony Orchestra, as well as the famous Jacob’s Pillow dance festival and top-notch dining, theater, and museums.

But few people think about visiting in the winter — which is a total shame. A winter Berkshires getaway offers all the charm of a Vermont ski town, minus the crowds and high prices, and it’s refreshingly unpretentious. Dress for warmth, not fashion, and to fit in, rent a Subaru, which seems to be the unofficial vehicle of the Berkshires.

Related: Resorts Hope Skiers Flock to Snow-Covered New England

“You can actually hear yourself think in the winter, and the stars at night are spectacular,” says screenwriter Andrew Bergman, who has had a home in the Berkshires for about 30 years. “It’s all about the natural beauty here.”


Jiminy Peak (Berkshires Visitors Bureau)

There are also plenty of options for snowy outdoor fun. The Berkshires, which encompass 32 towns on the western border of Massachusetts, are home to a handful of ski resorts: Catamount, Berkshire East, Jiminy Peak, Bousquet, Butternut, and tiny Otis Ridge. Jiminy Peak is the largest ski and snowboard resort in Southern New England and also has a terrain park. Though these small-scale resorts are not exactly Deer Valley, they’re perfect for a family ski weekend — you can navigate the parking lots and lift lines with ease.

If you want to try snowshoeing or cross-country skiing, guests staying at the family-friendly Cranwell Resort (where midweek rates start at $157) can rent gear from the pro shop and hit six miles of groomed trails on the property. The main requirement for these sports is warm clothing and determination; even my 2-year-old is able to snowshoe. Or head to Hilltop Orchards to rent equipment and explore three and a half miles of trails around the orchards and winery. After working up a sweat, go inside to warm up beside the fire in the barrel room , listen to Creedence Clearwater Revival on the loudspeaker, and nibble on a cider doughnut. Hilltop also offers a guided full moon snowshoe tour and a bonfire experience.

Or try catching your dinner out on the ice. Paul Tawczynski, of Charter the Berkshires, organizes ice-fishing excursions on more than 50 lakes in the area. “You can catch all the same fish you’d expect to catch in the summer, such as pike, salmon, trout, perch, and smelt,” he says. (The ice is about 30 inches thick so far this season.) Tawczynski also suggests exploring the area with a free “First Walk” hosted on the first day of the month, during which visitors can take a guided walk with a member of the Massachusetts Department of Conservation and Recreation.

Related: Look Hot in the Cold: the Sweetest Winter Travel Gear


Prairie Whale (Christina Valhouli)

During the summer, it’s tough to get a prime-time table at restaurants such as Alta, Nudel, and John Andrews, but you’ll have much better luck in the winter. While the lines outside cult classics like Baba Louie’s and the Gypsy Joynt are still long in the winter, beat the crowds at the farm-to-table Prairie Whale in Great Barrington (whose owner, Mark Firth, was behind Brooklyn restaurants Diner and Marlow & Sons). It attracts a mix of locals, hipsters from New York, and families, and the vibe is rustic farmhouse. Grab a table next to the wood-burning stove and replenish all those calories you burned skiing with a meal of fried chicken and collard greens. Meanwhile, the kids will be happy with a fat stack of buttermilk pancakes.

In Lenox, try the casual Jae’s Asian Bistro for a warming bowl of bibimbap or udon noodles. Or try Betty’s Pizza Shack, a brightly colored surf-themed restaurant with corrugated tin walls. The pizza and burritos are delicious, and Betty’s uses whole-milk mozzarella, antibiotic- and hormone-free chicken. Keep in mind, it’s cash only.

While some of the area’s biggest sights, such as Hancock Shaker Village and Edith Wharton’s home, The Mount, may be closed for the winter, there are still plenty of cultural choices. Hop in your four-wheel-drive car and wind your way up the snow-covered driveway to catch a glimpse of The Mount, or strap on snowshoes and admire the view from the snow; it’s impressive even from the outside. Or for a dose of modern art, head to Mass MOCA in North Adams. Spread over 13 acres and housed in renovated 19th-century factory buildings, the museum is one of the biggest in the U.S. for contemporary and visual arts. The Clark Art Institute, which reopened last summer after a $100 million renovation, has a large collection of Impressionist paintings.


Norman Rockwell Museum (Norman Rockwell Museum/Facebook)

No trip to the Berkshires is complete without a stop at the Norman Rockwell Museum. The iconic American painter lived in Stockbridge and famously depicted it in his “Stockbridge Main Street at Christmas” painting. Drive past Stockbridge today, and it pretty much looks the same (and don’t miss the Red Lion Inn). At the museum, head to the basement level to view the collection of Rockwell’s Saturday Evening Post covers.

While Rockwell depicted everyday Americana, to see how the one percent lived, pop into Ventfort Hall, one of the few Gilded Age mansions in the Berkshires still open to the public (most have been converted into luxury hotels, such as Canyon Ranch and Blantyre.) It was owned by banker J.P. Morgan’s sister, Sarah Morgan, and some scenes in The Cider House Rules were filmed here. Although it’s being painstakingly restored, the craftsmanship of the house, with its detailed wooden paneling and grand entrance hall, is superb. And for a juicy story, be sure to ask your tour guide about family member George Morgan, who scandalized society by marrying a geisha.

Related: Strike Up the Band for Summer in Berkshire Hills, Massachusetts

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