Stockbridge is an incredibly picturesque town, frozen in time in one of Norman Rockwell’s most famous paintings, Home For Christmas, also known as Stockbridge Main Street at Christmas. While the artist has brought plenty of attention to this town of under 2,000 residents, it has maintained its historic charm and small-town feel over the decades. And its shopping district is a wonderful place to explore. If you’re intent on visiting a small stretch of shops in Massachusetts, head to Stockbridge’s Main Street where you’ll find several locally-owned businesses. It’s the perfect way to spend an afternoon.

Set in the Berkshire's countryside, Stockbridge is a quaint small town that offers visitors plenty of attractions, restaurants, historical sites, and shops to explore. And the town's Main Street is the perfect place to spend an afternoon shopping at locally-owned stores.
Barry Winiker/ The Image Bank via Getty Images
Step back in time at the Williams & Sons Country Store located in a building that was first opened as a store in 1790. This old-fashioned general store sells a variety of gifts, penny candies, locally-crafted products, jams and jellies, and a whole lot more.
38 Main St, Stockbridge, MA 01262, USA
Williams & Sons Country Store/Facebook
If you're a music lover who enjoys vinyl, stop by Seven Arts Gift Shop, which also offers a selection of new and vintage clothing items and accessories. There's no other store quite like this in town.
44 Main St, Stockbridge, MA 01262, USA
7 Arts/Facebook

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Located in the Mews, Peace Love & Chocolate is not to be missed. This cafe and chocolate shop is a lovely place to spend some time and take a break from shopping along Main Street.
Jim Bromberg/Google
You may also want to take some chocolates home with you. From truffles to chocolate bars, turtles, and other delectable goods as well as unique gift items, you won't leave Peace Love & Chocolate empty-handed.
36 Main St, Stockbridge, MA 01262, USA
Peace Love & Chocolate/Facebook
Head down the alley at 44 Main Street and stumble into Prado de Lana Sheep Farm, a store filled with 100 percent wool yarn and wool products. The sheep the wool comes from live in a pasture in Southern Berkshire County.
44 Main St, Stockbridge, MA 01262, USA
Prado de Lana Sheep Farm/Facebook
While you're spending time on Main Street, you may as well pop into The Lost Lamb. Here you can pick up French pastries, coffee, sandwiches, soups, and more.
31 Main St, Stockbridge, MA 01262, USA
The Lost Lamb/Facebook

 

Spending time on Stockbridge’s Main Street certainly makes for a perfect afternoon. What town has your favorite stretch of shops in Massachusetts? Have you been to the shops on Main Street in Stockbridge? Let us know in the comments. You may also wish to explore the downtown areas of these small towns in Massachusetts.

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Stockbridge, MA, USA