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Overview

Stockbridge is a classic Berkshires town in the western part of Massachusetts popular with wealthy retired people and summer visitors. One of its most popular aspects is its proximity to Lenox and the Tanglewood Music Center, summer home of the Boston Symphony Orchestra. But there is more to this classic New England hill town. The 20th-century painter Norman Rockwell lived here for years and the town was inspiration for his work, much of which can be seen at the Norman Rockwell Museum. He is buried in Stockbridge Cemetery, which is also the site of the unusual Sedgewick Pie, burial grounds of the Sedgwick family and the freed family slave ...

Stockbridge is a classic Berkshires town in the western part of Massachusetts popular with wealthy retired people and summer visitors. One of its most popular aspects is its proximity to Lenox and the Tanglewood Music Center, summer home of the Boston Symphony Orchestra. But there is more to this classic New England hill town. The 20th-century painter Norman Rockwell lived here for years and the town was inspiration for his work, much of which can be seen at the Norman Rockwell Museum. He is buried in Stockbridge Cemetery, which is also the site of the unusual Sedgewick Pie, burial grounds of the Sedgwick family and the freed family slave Mumbet. St. Paul’s Church, designed by Charles McKim, has a LaFarge chancel window, a Tiffany nave window and an Augustus Saint-Gaudens baptistery. The highly acclaimed Berkshire Theatre Festival, held in Stockbridge, is conducted in a building designed by Stanford White. The prominent turn-of-the-20th-century architectural firm of McKim, Mead and White also designed Naumkeag, family home of the Choate family, and its “Blue Stairs” are an outstanding feature. Also be sure to see the 1739 Mission House on Main Street.

Stillman Rogers
About the Expert

Stillman Rogers has written more than two dozen guidebooks, including Adventure Guide to Canada's Atlantic Provinces, Guide to Eastern Canada, and Adventure Guide to the Chesapeake.

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Facts at a Glance

Climate

  • Best Time to Visit:

    The history and demographic of Stockbridge make it a place to visit any time of year. Schedules for festivals vary but generally occur during the summer months. Tanglewood is in August. The area around is beautiful for drives, bicycling and hiking from spring through autumn.