Travel Guide to Stockbridge and Its 5 Best Attractions

"The best of America, the best of New England," is how the American artist Norman Rockwell characterized the small town of Stockbridge. Sequestered in a green valley, surrounded by the rolling Berkshire Hills, and just 2.5 hours north of New York City and two hours west of Boston, Stockbridge is both a gateway to the great Massachusetts outdoors and one of the region’s cultural hubs. In the summer, the Tanglewood Festival showcases music ranging from choral symphonies to contemporary jazz. And as Christmas approaches, the town’s snow-swathed Main Street celebrates with a range of activities, topped off by a recreation of the 1950s Norman Rockwell painting that fixed the street in the American imagination. Beyond the sparkle of the town rise wooded hills and hikers can use Stockbridge as a launching point for stretches of the Appalachian Trail.

Art and illustration at the Norman Rockwell Museum

Photo by Jennifer Yang via Flickr

Norman Rockwell is among twentieth century America’s most cherished illustrators, and was also a very well-respected painter. A stately white building in the heart of Stockbridge, the town in which Rockwell passed his last twenty years, houses a meticulously thought-out exhibition of his work. All 323 of his cover illustrations for the Saturday Evening Post are on display, and in pride of place is his depiction of a bright, lively, snow-covered evening on Stockbridge Main Street.

Explore orchards, meadows and geological curiosities on the Tyringham Cobble Loop

Photo by Dan Canale via Flickr

For those seeking an experience of the outdoors alongside all the history and culture that Stockbridge offers, a fifteen minute drive east of town brings one to the Tyringham Valley. The Appalachian Trail cuts through here, and a two-mile, family friendly circuit encompasses a unique geological curiosity. A short but sharp uphill climb from the valley floor, through orchards and wildflower meadows, leads to the Tyringham Cobble – an exposed slab of gneiss rising above the trees.

History, gastronomy and revelry mingle at the Red Lion Inn

Photo by Frank Swift via Flickr

The Red Lion Inn is a truly unique place to eat or sleep. It opened its tavern doors in 1773, weathered the War of Independence, and is now firmly established as one of the must-visit eateries in the Stockbridge area. Its menu serves hearty plates of fish and meat with a modern culinary twist. An annex, the Lion’s Den, offers a more laid-back vibe with live entertainment nightly. The accommodations, meanwhile, consist of 125 individually decorated guestrooms, with a heated pool and hot tub.

Natural tranquility at the Berkshire Botanical Garden

Photo by Sonja Stark via Flickr

A herb garden, water garden, vegetable garden, patches of perennials and small clusters of trees make the Berkshire Botanical Garden a colorful and varied space to spend some time. It is run with a strong community ethic, and workshops are held year round to cultivate a sense of the pleasures of gardening. Each October the garden hosts a Harvest Festival, celebrating the earth’s bounty with music, crafts, artisan stalls and a range of activities for kids, making it a perfect stop on a family visit to Stockbridge.

Tanglewood: Classical music concerts in a pastoral setting

Photo by Robert Kendall via Flickr

Every summer, the Boston Symphony Orchestra takes up residence in Tanglewood, a cluster of concert halls situated in pastoral countryside just outside the village of Lenox, a few minutes out of Stockbridge. The Orchestra’s arrival precipitates the annual Tanglewood Music Festival, one of America’s premier classical music festivals. On indoor and outdoor stages, and for several weeks of the summer, the Boston Symphony Orchestra headline a series of concerts showcasing musicians from a broad range of styles. Strolling past different stages and buildings, Beethoven might give way to musical theater, contemporary jazz, pop or a cappella opera.