Where to Stay and What to Do in the Berkshires
The Berkshires, in western Massachusetts, have long drawn creative names-Melville, Hawthorne, Wharton and Rockwell among them-and the region's cultural pull remains strong. Larger towns anchor a visit: Great Barrington, Lenox and Stockbridge in the west, and North Adams in the northeast.
Among the newer places to stay is Prospect Berkshires, which opened in 2025 in Egremont with 49 Scandinavian-inspired cabins along Prospect Lake, where swimming, kayaking and paddleboarding are encouraged. Saunas sit throughout the property, including two on the lake, alongside a tennis court and a pool. Little Cat Lodge, just down the road and technically in New York, leans alpine-chic meets motor lodge. In Richmond, The Inn at Kenmore Hall is a boutique hotel in a Georgian home.
For something traditional, the Red Lion Inn in Stockbridge has operated since 1773; rebuilt after a fire at the turn of the 20th century, it has hosted multiple US presidents, Judy Garland and Bob Dylan, and was once a workplace of Real Housewives of New York City alum Dorinda Medley. Near the art action, Tourists Welcome in North Adams sits a six-minute drive from MASS MoCA and three minutes from Williams College, with 46 rooms plus two nearby private homes. In Lenox, 33 Main and the nine-bedroom Doctor Sax House offer boutique stays.
Shopping has a new draw: Walker Street Market, a design gallery with works from more than 70 contemporary artists, opened in July on a main drag in Lenox. In Great Barrington, the Berkshire Galleries suits antiquing, and Main Street rewards a leisurely stroll, with shops including Fluff Alpaca and One Mercantile, plus SETT next door for kitchen goods. Fuel is a popular spot for breakfast sandwiches and coffee, and SoCo Creamery serves ice cream.
A visit would not be complete without Tanglewood or Jacob's Pillow for live music or dance, or MASS MoCA, one of the largest museums in the United States. In Stockbridge, the Norman Rockwell Museum holds almost 1,000 original drawings and paintings. Hancock Shaker Village in Pittsfield is family-friendly, with farm animals, and the Shaker Museum is due in the region in 2028.
The landscape-Taconic Mountains, the Housatonic and Connecticut Rivers, and plenty of woods-makes for year-round splendor, with hiking and winter skiing. Monument Mountain's three trails, each under three miles, offer some of the best views of the Housatonic River Valley, especially at sunrise. Mount Greylock, the state's highest point, provides a view of the Appalachian Trail, and Stockbridge's Charcoal Trail leads to Olivia's Overlook. Chesterwood, the sculpture garden and studio of Daniel Chester French, offers weekend guided tours from May through October, and Edith Wharton's Lenox home, The Mount, is open to visitors, with a 45-minute garden tour.
Dining leans quality over quantity. Prairie Whale, which opened in 2012, feels like an old-school tavern, with excellent fries and strong cocktails. High Lawn Farm draws families for ice cream and baby cows, and Rubiner's Cheesemongers in Great Barrington is a local favorite. The Cliff House at Prospect Berkshires is among the more upscale options, with lakeside views and locally sourced ingredients. No Comply, an alcohol-free restaurant with a skater spirit, landed on Bon Appetit's Best New Breakfast Spots list in 2025. No. Six Depot in West Stockbridge is a husband-and-wife roastery, and Pizzeria Boema serves Neapolitan-style pizza with Monday Night Jazz in summer. Bistro Box in Great Barrington runs seasonally from April through November, and Heirloom Lodge in West Stockbridge offers farm-to-table fare with a focus on family-run vineyards.