There’s a good reason why the town of Stockbridge in Massachusetts looks like a Norman Rockwell Christmas town. Maybe you know, maybe you don’t, but the renowned artist made the town of Stockbridge famous in one of his best-known paintings, Stockbridge Main Street at Christmas. So, if you’ve ever visited and thought that this town looks like it is straight out of a Norman Rockwell painting, well, that’s because it is! Come along as we show you why it’s so enchanting!

Some towns around the country may look as though they were featured in a Norman Rockwell painting.
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In Massachusetts, there is a small town that actually was featured in one of the artist's best-known paintings.
The small Berkshires town of Stockbridge was the main subject of Rockwell's painting, Stockbridge Main Street at Christmas.
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Because of this painting, Stockbridge became famous.
To give a bit of background, Norman Rockwell had lived in Stockbridge for 25 years.
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His art studio, which was moved from its original site to the grounds of the Norman Rockwell Museum, can still be visited today.

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The artist's love for the town is quite apparent in his painting...
JOSEPH PREZIOSO / Contributor/AFP via Getty Images
...and if you take a stroll down Stockbridge's Main Street, you may feel as though you are walking through a piece of his art.
This town certainly does Christmas in the most enchanting ways imaginable.
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This year, the town will celebrate its 34th annual Stockbridge Main Street at Christmas celebration from December 1 through December 3, 2023.
During the celebration, there will be a recreation of the Rockwell painting that made this town famous...
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...as well as activities, attractions, performances, a historic holiday property tour, and classic 1950s cars on display along Main Street. Its one of the best places to enjoy the holidays in Massachusetts!
And while you're in town, visit Naumkeag Winterlights.
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This is a gorgeous garden display of twinkling lights on the Naumkeag Estate.

We hope you agree that there’s nothing more charming than the Stockbridge Main Street at Christmas! Have you ever visited Stockbridge, the Norman Rockwell Christmas town in Massachusetts? Let us know in the comments.

While you’re in town, you should also take in Stockbridge’s many historical sites!

For those who love winter hiking, you can find some great trails in and around the area by going to the AllTrails website.

If you’re still in the mood for more Massachusetts adventures, take a look at this video about the Top 10 Places to Visit in Massachusetts:

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More to Explore

Out And About In Massachusetts

Lysa Allman-Baldwin | November 22, 2023

Where can we find family-friendly hiking trails in Massachusetts?

  • The Chapel Brook Falls Trail in Ashfield leads to the Chapel Brook cascade and the peak of Pony Mountain.
  • The Fort Hill Trail in Eastham is a beach trail that is also great for birdwatching and picnicking.
  • Bash Bish Falls Trail in Mount Washington leads to the tallest waterfall in Massachusetts.

Read on to learn more about some of the many other family-friendly hiking trails in Massachusetts.

Where can we find corn mazes in Massachusetts?

  • Nessralla Farm in Halifax features a fun corn maze in addition to hayrides, a hay bale pyramid, and other exciting autumn-themed games.
  • Vineyard Farm in West Bridgewater features very creative themed-mazes every year, in addition to  an array of related activities.
  • The Davis Mega Maze in Sterling has been called the king of all corn mazes with 8 acres of corn, 7 maze levels, and 3 miles of paths.

Read on to learn more about some of the many other exciting corn mazes in Massachusetts.

Where can we find scenic drives in Massachusetts?

  • The Route 116 Scenic Byway goes through  Conway, Cheshire, Adams, Savoy, and Plainfield, just to name a few.
  • The Route 112 Scenic Byway winds from north to south from the Vermont border to the town of Huntington.
  • The Mount Greylock Scenic Byway crosses state lines but in Massachusetts it traverses past sites like the Ashuwillticook Rail Trail, Bascom Lodge, and Natural Bridge State Park.

Read on to learn more about some of the many other wonderful scenic drives in Massachusetts.

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Stockbridge, MA, USA