Stockbridge began its life, as a community with that name, as a Mohican town. In 1730, people of the Mohican nation and offered an exchange of land in the southern Berkshires for a township within the Commonwealth. Their descendants live in Wisconsin now as the Stockbridge-Munsee Nation, and they return often.

The house where John Sargent lived as the first missionary in the new town is a museum now on the Main Street, not far from the 1773 Red Lion Inn. Within a few years the town would be home to Revolutionary War veteran Agrippa Hull and Elizabeth Freeman, the woman who won her freedom and proved slavery illegal in the new state of Massachusetts — and to the 18th-century novelist Catherine Sedgwick

In the 19th century, Daniel Chester French turned an old farm into his studio as he created the Lincoln Memorial. Chesterwood is a museum now with his house and studio, gardens and trails, and an annual contemporary sculpture Show.

And in the 20th century, as the Berkshire Theatre Group founded its campus here, Norman Rockwell took up his easel, painting the changing faces of America through World War II and into the 1960s. His studio is also at the center of a museum here, with shows of contemporary illustrators alongside his work, and a pathway through apple trees to the river.

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Emma Rothenberg-Ware / Berkshire Theatre Group

Berkshire Theatre Group

With classics like Fiorello and contemporary work, Berkshire Theatre Group merges two historic theaters — the one of the county’s oldest continuously running performance companies, the Berkshire Theatre Festival in Stockbridge, and the Colonial Theatre in Pittsfield, built in 1903 and re-opened in 2006.

Berkshire Botanical Garden / Photo by Kate Abbott

Berkshire Botanical Garden

In a quiet corner of Stockbridge, the Berkshire Botanical Garden has cared for 20 acres of land since 1934. The gardens open to visitors from May to early October, with art exhibits, talks and events, classes and workshops year-round.

Photo by Kate Abbott


The gardens of the Choate family’s Gilded Age ‘cottage’ have a name around the world for their Blue Stairs, tree peonies and roses, and they invite the community in year-round.

Paul Rocheleau / Chesterwood


In a studio with tall windows letting in the north light, Daniel Chester French created the figure of Abraham Lincoln for the Lincoln Memorial in Washington D.C. Today contemporary sculpture lines the paths and gardens in the summer and fall.

Photo by Kate Abbott


Stockbridge protects its old New England Main Street, with the Red Lion Inn on the corner. On the right weekend, you might see a parade of coaches and four driving up Route 7 — or classic cars lining the downtown.

Image courtesy of IS183

IS183 Art School

In an old schoolhouse in Stockbridge, IS183 has been teaching hands-on art since 1991. Today the art school also holds classes at schools and museums and downtown gathering places across the county.

Photo by Kate Abbott

Red Lion Inn

The Red Lion Inn has stood centrally on Main Street since 1773, when it served as a stage coach between Boston and Albany. The old clapboard building has a history going back to the Revolution, and today it brings locals and visitors to its restaurants and shop of goods from local artists and artisans.