5 Best Things to Do in the Berkshires

Only have a day or two? From soaking up world-class art to reveling in mountain views, here are five of the very best things to do in the Berkshires region of Massachusetts.

By Yankee Staff

Aug 23 2022

Berkshires5_Tanglewood_Hilary Scott


Photo Credit : Hilary Scott
Please note that many establishments throughout New England have modified their hours and/or operations in response to COVID-19. Always check for the latest information before making travel plans.
Ever since the 19th century, when well-to-do city dwellers built summer homes here, Massachusetts’s far-western Berkshire County has beckoned to visitors with its natural beauty and the cooler breezes of its mountain ridges and valleys. Dubbed the Berkshires, this region is today equally well known for its cultural offerings, which range from award-winning art museums to nationally renowned music, dance, and theater festivals. Plus, its strong agricultural pedigree guarantees farm-fresh produce just about anywhere you look, including on the menus of a new crop of restaurants rising in the area. You could easily spend a week or more exploring this fabled Massachusetts region and its plethora of nature-made and manmade attractions. But if you have just a day or two, here are the five best things to do in the Berkshires region of Massachusetts.
Hikers in the Berkshires can take their pick of challenging routes — e.g., tackling 3,491-foot Mount Greylock — or more moderate treks, like Olivia’s Overlook in Lenox, pictured.
Photo Credit : Tim Grafft/MOTT

5 Best Things to Do in the Berkshires

Pay a Visit to Mass MoCA

How did the largest contemporary-art museum in North America wind up in North Adams? The short story is, it ingeniously solved two problems: what to do with the vast decaying buildings of a shuttered 16-acre manufacturing complex, and where to exhibit large-scale contemporary art. Ever since opening in 1999, the Massachusetts Museum of Contemporary Art has been a must-see on any Berkshires bucket list. Gigantic gallery spaces let artists unleash their creativity through fascinating installations, highlighted by more than 100 large-scale wall drawings designed by Connecticut native Sol LeWitt. But museum lovers shouldn’t stop there: Just next door to North Adams is the college hamlet of Williamstown, which boasts both the highly regarded Williams College Museum of Art and the stunning Clark Art Institute. Meanwhile, in southern Berkshire County there’s Stockbridge, home to the museum and studio of beloved illustrator Norman Rockwell as well as the 1896 estate and studio of sculptor Daniel Chester French.
5 Best Things to Do in the Berkshires
Sol LeWitt’s Wall Drawing #880, part of the LeWitt wall drawing retrospective at Mass MoCA.
Photo Credit : Kevin Kennefick

Time-Travel at Hancock Shaker Village

Built in 1826, the Round Stone Barn at Pittsfield’s Hancock Shaker Village is the perfect introduction to the Shaker genius for creative farming: The radial stalls are an elegant display of labor-saving animal husbandry. The iconic barn is the centerpiece of the restored village, one of the largest and most successful of the Shaker communities that once stretched from Kentucky to Maine. Called “the City of Peace” by the Shakers who once dwelled here, the Hancock settlement today is home to 20 original buildings, a working farm, a scenic walking trail, and a significant cache of Shaker furniture and artifacts. 

5 Best Things to Do in the Berkshires
Looking out toward the Round Stone Barn at Hancock Shaker Village in Pittsfield.
Photo Credit : Heather Marcus

Catch a Live Performance

In the warmer months, culture vultures can take their pick of first-class performing arts in the Berkshires. In Lenox, there’s Tanglewood, the summer home of the Boston Symphony Orchestra, which invites music lovers to spread a blanket on the lawn and enjoy a picnic serenade. In Becket, look for Jacob’s Pillow: a 220-acre National Historic Landmark, a recipient of the prestigious National Medal of Arts, and home to America’s longest-running international dance festival. And in Williamstown, there’s the Williamstown Theatre Festival, a tradition since 1955 that puts the spotlight on both classic plays and bold new works. Plus, check out the schedules for the Berkshire Theatre Group and Shakespeare & Co.
5 Best Things to Do in the Berkshires
Kicking back on the lawn at Tanglewood in Lenox.
Photo Credit : Hilary Scott

Go Take a Berkshires Hike

The highest point in Massachusetts, Mount Greylock in Adams has been a favorite of outdoor enthusiasts since the early 19th century, capturing the imagination of Hawthorne, Thoreau, and Melville (who even dedicated his novel Pierre to Greylock’s “Most Excellent Purple Majesty”). Today it’s the centerpiece of some 12,500 acres of state reservation land and an unbeatable challenge for adventurous hikers. The easiest hike to the top, a loop primarily set on the Cheshire Harbor Trail, still requires about four to five hours of moderate to strenuous effort. The payoff: looking out at a landscape that encompasses five states, several mountain ranges, and an ocean of greenery.

Other popular hikes in the Berkshires include Monument Mountain in Great Barrington, Stony Ledge in Williamstown, Bash Bish Falls in Mount Washington, and Olivia’s Outlook in Lenox.
The Veterans War Memorial Tower at the summit of Mount Greylock in Adams.
Photo Credit : Massachusetts Office of Travel & Tourism

Eat Great in Great Barrington

Yankee senior food editor Amy Traverso recently named the Berkshires town of Great Barrington as one of the 10 Best Foodie Getaways in New England, saying it “balances its identity as a weekend destination for city folk with an eat-local, farm-forward community of dedicated, food-savvy year-rounders.” Taste the results by heading to Railroad Street and Main Street, home to such tempting eateries such as BizenThe Prairie Whale, GB Eats, Twoflower Cafe, Marjoram + Roux, SoCo Creamery, and more. And, Amy adds: “Don’t miss a stop at Guido’s Fresh Marketplace, the kind of green/gourmet/everyday supermarket that every town deserves, but few have.” Have your own list of the very best things to do in the Berkshires? Leave your picks in the comments below!

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