Get itinerary inspiration with these group tour stops in The Berkshires, Massachusetts.

“The Berkshires are one of the most group-friendly destinations in the world! Less than three hours from New York City and Boston, we have no traffic and parking is abundant, not to mention the views from your coach are spectacular. Outdoor excursions, world-class culture, an array of lodging options and a deeply rooted food culture set this region apart.” Lindsey Schmid, senior vice president of tourism and marketing, 1Berkshire


Old Baldy Wildlife Sanctuary in Otis is a 154-acre property nestled within a larger area of about 2,000 acres of conserved land. A short but steep trail to the summit rewards hikers with a 360-degree vista of the surrounding sugar maple, white ash and basswood forests.

In Pittsfield, a new section of the Ashuwillticook Rail Trail is open from Crane Avenue to the Berkshire Mall, adding 3 miles to the existing trail.

Trails at Mass Audubon’s Pleasant Valley Wildlife Sanctuary in Lenox include the Yokun/Beaver Lodge Trails Loop. This easy one-hour walk provides views of beaver ponds and the Lenox Mountain ridge.


Norman Rockwell Museum
Credit: Norman Rockwell Museum

The Berkshires are full of visual art. Set up tours at MASS MoCA (the Massachusetts Museum of Contemporary Art), The Clark Art Institute and the Norman Rockwell Museum.


Tamarack Hollow Nature & Cultural Center offers naturalist-led environmental education, such as hikes and treks throughout western Massachusetts, nature awareness and appreciation programs, and programs on edible and medicinal plants and trees.

Enjoy Private group tours at Berkshire Botanical Garden in Stockbridge focus on seasonal highlights and the display
gardens. The season runs from May 1 through Columbus Day. 

Jacob’s Pillow dance festival in Becket celebrated its 90th anniversary season in summer 2022.

Visitors can explore the grounds at Tanglewood, the summer home of the Boston Symphony Orchestra, year-round, free of charge. Group tickets are available for concerts and events.

Chesterwood, the historic home, studio and gardens of 20th-century sculptor Daniel Chester French, is open from spring through fall. This season, the main residence cannot be toured due to a rehabilitation project.



Main image: Ashuwillticook Rail Trail; Credit: Massachusetts Office of Travel and Tourism