Stretching across the western edge of Massachusetts, the Berkshire Mountains are one of New England’s best-kept open secrets. The region mixes world-class arts institutions with genuine wilderness — you can spend a morning hiking to a mountain summit, an afternoon in a museum ranked among the finest in the country, and an evening at an outdoor concert under the stars.

Our properties in Williamstown sit at the northern tip of the Berkshires, ideally placed for day trips in every direction: south toward Lenox and Stockbridge, east toward the Pioneer Valley, or north into Vermont.

Highlights by Category

Music

•       Tanglewood Music Center, Lenox — Home of the Boston Symphony Orchestra in summer. One of the great outdoor music experiences in America. 25 min from Williamstown.

•       Solid Sound Festival, North Adams — Wilco’s biennial music and arts festival, held at MassMoCA. Check dates when planning your trip.

Art & Museums

•       MassMoCA, North Adams — One of the largest contemporary art museums in the world, housed in a spectacular converted mill complex. 10 min.

•       Sterling and Francine Clark Art Institute, Williamstown — World-class collection from the Renaissance to the Impressionists. Gorgeous grounds. 5 min.

•       Norman Rockwell Museum, Stockbridge — The definitive collection of Norman Rockwell’s work, in the town where he lived and painted. 45 min.

•       Williams College Museum of Art, Williamstown — Free admission, outstanding permanent collection. 5 min.

•       Berkshire Museum, Pittsfield — Art, natural history, and science. Great for families. 20 min.

Hiking & Outdoors

•       Pine Cobble Trail, Williamstown — A local favorite: steep, rewarding, and spectacular views from the summit. 10 min.

•       Mount Greylock, Adams — The highest point in Massachusetts (3,491 ft). Multiple trails, a War Memorial Tower at the summit, and views stretching into five states. 30 min.

•       Cascade Falls, North Adams — A beautiful, accessible waterfall hike. 15 min.

•       Margaret Lindley Park, Williamstown — Swimming hole, picnic area, and family-friendly outdoor space. 15 min.

•       Taconic Crest Trail — A long-distance ridgeline trail crossing Massachusetts, New York, and Vermont. Accessible from multiple trailheads near Williamstown.

Skiing & Winter

•       Jiminy Peak Mountain Resort, Hancock — The region’s main ski area, with trails for all levels. 20 min.

•       Butternut Ski Area, Great Barrington — A smaller, family-friendly alternative. 1 hr.

Small Towns Worth Exploring

•       Lenox — Elegant, leafy, and home to Tanglewood. Great restaurants and inns.

•       Stockbridge — A quintessential New England village, famous for its Norman Rockwell connection.

•       Great Barrington — The liveliest Berkshires town south of Pittsfield: excellent food, shopping, and a vibrant arts scene.

•       North Adams — A former mill town reinvented as an arts hub, anchored by MassMoCA.

•       Bennington, VT — Just 20 minutes north, with its own history, arts scene, and the famous Bennington Battle Monument.