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Itineraries & Activities

Stockbridge and the Berkshires offer visitors numerous cultural and historic attractions. Below are sample travel itineraries for visiting journalists; please contact us to discuss other options.

A Season of Inspiration for Groups at Berkshire Gardens

The Berkshires—Exceptional Fun for Heartwarming Reunions

American Icons and More in the Berkshires

Gilded Age Tour of the Berkshires

Groups Can Explore Extraordinary Art in Uncommon Places in the Berkshires

For additional travel itineraries and assistance in planning a familiarization trip to the Berkshires, contact fams@berkshires.org


Downtown Stockbridge is a wonderful place for groups to wander, explore, shop, and dine. A National Trust Historic District, Main Street is well known as the scene of Norman Rockwell’s Main Street at Christmas painting. Click here for a PDF listing of businesses and attractions that can be enjoyed on foot. For general information, please contact the Stockbridge Chamber of Commerce.