Stockbridge is known for its “Berkshire cottages,” impressively large estates originally built during the Gilded Age by wealthy summer residents.
The names Norman Rockwell and Stockbridge go hand-in-hand, thanks to the artist’s many works based on his town—the community still reenacts his Stockbridge Main Street at Christmas painting each year during its holiday festival. But it was also the home of luminaries like sculptor Daniel Chester French and the Sedgwick family. With its antique look and busy shops, galleries, and cafes, the downtown makes a worthy day trip at any time of year. Or go hiking, kayaking, boating, swimming, or paddleboarding on Stockbridge Bowl, one of the most scenic spots in the Berkshires.
For decades, Kripalu has been known for its health and wellness programs, including yoga, meditation, and nutrition. It offers a comprehensive slate of programming throughout the year, with workshops on fitness, creativity, writing, and personal and spiritual connection.
Built as the home of 19th-century diplomat Joseph Hodges Choate, Naumkeag was designed by internationally renowned architect Stanford White. Tour the home and grounds, or attend a special event, like cocktails in the garden, a Halloween haunted house, or Winterlights, when the grounds are decked out with thousands of holiday lights.
The world’s largest collection of original Norman Rockwell art resides here. The museum also presents the best in American illustration, photography, and animation, and hosts numerous workshops and artist talks.