A visit to the Berkshires would not be complete, in my opinion, without a visit to Tanglewood or Jacob’s Pillow for some live music or dance, respectively. MASS MoCA is also a must-see; the former industrial space, impressive in its own right, is now one of the largest museums in the United States and is venerated for its contemporary programming. Further south in Stockbridge, the Norman Rockwell Museum in the artist’s hometown has a collection of almost 1,000 original drawings and paintings.
Fans of the Shakers won’t be disappointed. In Pittsfield, Hancock Shaker Village is a wholesome, family-friendly affair with farm animals included. In 2028, the region will also be home to the Shaker Museum, a second destination dedicated to the group’s pursuits in Chatham, New York. In the meantime, the Shaker Outpost is hosting seasonal exhibitions.
The natural beauty in this part of Massachusetts really can’t be understated. The landscape—with the Taconic Mountains, the Housatonic and Connecticut Rivers, and no shortage of woods—make for year-round splendor (the leaf peeping season is deeply underrated). The area also provides endless hiking and, in the winter, multiple skiing ranges for a little more active adventure. 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 Stockbridge Bowl lake and the surrounding area.
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—the 45-minute garden tour is especially stunning in the spring.
