What to Do in The Berkshires

New Yorkers have the Catskills. Philadelphians have the Poconos. Bostonians have the Berkshires. But while this western Massachusetts mountain escape destination is a favorite for families, luxury retreat-seekers and outdoor adventurers in Beantown, the Berkshires also attracts its fair share of travelers from other parts of the country. If you’re among them, here’s everything you need to do during your very first visit.

Get Outside and Soak Up the Season

The Berkshires is truly a four-season destination, with something to do no matter if you visit in spring, summer, fall or winter. During the colder months, you’ll find skiing aplenty, plus other winter sports, if you prefer something a little more low-key. During the summer, hiking and biking opportunities are abundant. Want something really high-energy? Try some white-water rafting. Prefer something more relaxing and chill? Get in a round of golf or head out in a kayak.

Explore the Berkshires Arts and Culture Scene

While the Berkshires might be best known for its outdoor fun, it also offers arts and culture in spades. In addition to hosting all sorts of fun, arts-related festivals and events (like the Boston Symphony Orchestra’s summer residency at the Lenox Tanglewood Music Center), the region also boasts a large number of museums and historic sites.

Visit the Clark Art Institute to explore works from renowned masters. If you’d rather focus on just one artistic master, though, you can visit the Norman Rockwell Museum.

For something more culture and history than art, visit the 1700s Bidwell House Museum, The Mount Home of Edith Wharton or the Ventfort Hall Mansion and Gilded Age Museum, built by the JP Morgan family.

Squeeze in Some Retail Therapy

Even if shopping isn’t your main priority when you travel, it’s still worth your time to check out the shopping scene throughout the Berkshires. You’ll find outlet stores offering great deals on favorite brands, local boutiques in adorable mountain town settings and more. The area is also a great spot for antiquing!

Sip on the Local Fare

Explore the Berkshires’ best watering holes, when you stop in at some of the region’s top distilleries, breweries and wineries. Whatever your favorite way to drink, you can find a way to do it, thanks to the area’s many local makers.

Taste the Local Treats

And while you’re sipping on the local brews and such, don’t forget to also enjoy some of the local foods and produce, too. Whether you stop by a local dairy and sample the cheese, or pick your own berries or apples as the seasons allow, you can find a range of orchards and farms that welcome travelers for a visit.

To get started, try a stop by High Lawn Farm, a historic dairy farm serving artisanal products; Furnace Brook Winery at Hilltop Orchard, for both apple picking and wine tasting in one spot; or Maple Corner Farm, if you’re lucky enough to be visiting the region during maple sugaring season.

Need More?

There’s so much to do in the Berkshires, that our list of top-recommended activities just scratches the surface. For more recommendations — including recommendations on where to stay, dine and shop while you’re in the area — check out the Discovery Map Berkshires guide.