The Best Things to Do in the Berkshires—and Where to Stay

26.09.2024 - 16:15 / cntraveler.com / Edith Wharton

There’s never a wrong time of year to visit the Berkshires, the mountainous stretch of western Massachusetts located just 140 miles north of New York City. You can thank the fall’s vibrant display of foliage, summer’s Tanglewood music festival that draws crowds from all over the world, and a steady tide of new hotel openings to take advantage of as cozy winter getaways and for ski season. The region also has strong roots as an artists community, with a robust community of galleries, independent boutiques, and museums. And for city dwellers looking to stretch their legs, the Berkshires is also home to scenic hiking trails and winter slopes for every activity and ability level.

There are plenty of similarities between cozy Catskills downtowns like Hudson and the Berkshires’ Great Barrington—as well as the charming hotel scenes of Kingston, New York, and Lenox, Massachusetts. Whether you’re looking to maximize your time outdoors during the day and enjoy a quality culinary scene in the evening, or simply want to slow down for a weekend of relaxation and idle shopping, here’s how to make the most out of this iconic, westernmost swath of Massachusetts.

The Massachusetts Museum of Contemporary Art,or MASS MoCa, is located in North Adams and is one of the largest contemporary art museums in the US.

It would be easy to spend a full week just visiting the museums scattered across the Berkshires, so you'd be remiss not to at least sample a few. Start in North Adams at famed contemporary art hub MASS MoCa to make your way through the massive collection of Sol Lewitt’s large-scale wall drawings, as well as nine installations from “master of light” James Turrell. Further south in Stockbridge, the Norman Rockwell Museum features almost 1,000 original drawings and paintings in the artist’s hometown, including iconic covers from The Saturday Evening Post and MAD Magazine.

To enjoy art outdoors, guided tours are available on weekends from May through October at Chesterwood, a sculpture garden and studio that once belonged to Daniel Chester French, an artist who crafted, among many other pieces, the monumental Lincoln Memorial sculpture in Washington, DC. For the literary-inclined, author Edith Wharton’s Lenox home, The Mount, is open to visitors—and the 45-minute garden tour is especially stunning in the spring.

For one of the best views of the Housatonic River Valley (especially at sunrise), hike up Monument Mountain's three trails, each of which are under three miles long. Or to get a view of the Appalachian Trail, hike up Mount Greylock, which also happens to be home to the highest point in the state of Massachusetts. And in Stockbridge, the Charcoal Trail leads to Olivia’s Overlook for a stunning vantage point of