Stockbridge's ready accessibility to Boston and New York (about 2 1/2 hr. from each and reachable by rail since the mid-19th century) transformed the original frontier settlement into a Gilded Age summer retreat for the rich. The town has long been popular with artists and writers as well. Illustrator Norman Rockwell, who lived here for 25 years, rendered the Main Street of his adopted town in a famous painting. Along and near Main Street are a number of historic homes and other attractions, enough to fill up a long weekend, even without the Tanglewood concert season in nearby Lenox. One of the Berkshires' hottest destinations, Stockbridge is inevitably jammed on warm weekends and during foliage season. A prominent event is the Christmas celebration on the first Sunday in December, when over 50 antique cars are parked along Main Street to help re-create the scene painted by Norman Rockwell decades ago.
Stockbridge lies 7 miles north of Great Barrington and 6 miles south of Lenox. The Stockbridge Chamber of Commerce (tel. 413/298-5200; www.stockbridgechamber.org) maintains an information booth opposite the row of stores depicted by Rockwell. It's open May through October.
