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12 Fun Things to Do in Stockbridge, MA: Artsy Berkshires Hotspot

An old-fashioned yellow house with dark green shutters and a large porch set among trees at the end of a driveway in Stockbridge, Massachusetts.

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Join me on a visit to Stockbridge, MA: this is the heart of the Berkshires, where the Housatonic River meets the Appalachian Trail. For more than 300 years, Stockbridge has been a popular destination for visitors and a home to artists, writers, intellectuals — and the occasional travel blogger!

Stockbridge is one of my favorite towns in the Berkshires — because it’s exactly what your mind pictures when you dream of small town New England. So much of Stockbridge is straight out of a postcard. And as a Massachusetts native who has traveled all over her home state, I can’t believe it took me until my thirties to finally visit!

Stockbridge was originally inhabited by the Mohican Indigenous tribe. In 1739, English settlers arrived and purchased the land, establishing Stockbridge Township. In the 19th century, Stockbridge became a popular summer destination for wealthy New Yorkers and Bostonians who were drawn to its beautiful scenery, cooler climate, and cultural attractions.

Today, Stockbridge is an essential stop for any weekend Berkshires getaway. The town is home to some of the best museums in the region, art galleries, theaters, shops and restaurants. The town is also surrounded by beautiful scenery, with hiking trails, waterfalls, and a beautiful lake. 

But what I love most about Stockbridge is driving through the quiet streets and admiring all the old homes tucked into the hills. It looks straight out of a Norman Rockwell painting. Which makes sense because Norman Rockwell called Stockbridge home for many years! He even has a museum dedicated to his work here in Stockbridge.

Whether you’re coming for a theater-filled summer getaway or the springtime flower festivals, a cozy winter escape or the best of fall foliage, Stockbridge is a year-round destination you’re going to love.

(Planning a trip to the Berkshires? Be sure to check out the Best Things to Do in the Berkshires and my guide to the Towns of the Berkshires.)

This post was published in January 2024 and co-written by Adventurous Kate and Susan Stephens.

Things to Do in Stockbridge, MA

Explore Main Street and Downtown Stockbridge

The heart of Stockbridge lies in its historic downtown area, filled with wonderful art galleries, specialty shops, cozy cafes, and town offices. On Main Street, manicured lawns are interspersed with the quiet…

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