When you think of small town life, nostalgic main streets and classic Americana, the town Stockbridge is probably what you’re picturing in your head. That’s because the most iconic images of New England were based on this sleepy town. Read on to learn why Stockbridge is the epitome of old-fashioned charm and beauty.

Stockbridge is one of Massachusetts' most picturesque small towns.
Flickr/MOTT
Normal Rockwell, the artist responsible for works like Rosie the Riveter and the famous covers of the Saturday Evening post, was a resident of Stockbridge. He used the town as a model for much of his work.
Flickr/Jerry and Pat Donaho
Rockwell frequently used Stockbridge residents in his art, such as local policeman William Obanhein in "Policeman with Boys" and "After the Prom."
Flickr/James Vaughan (Estate of Norman Rockwell)
Stockbridge’s Main Street looks almost exactly as it did when Rockwell painted it.
Flickr/Kindra Cline, MOTT
The Norman Rockwell Museum pays tribute to the art of this classic American painter. It is home to 574 works by Rockwell, as well as countless photographs, letters and memorabilia from his life.
Flickr/MOTT

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The museum in springtime is a work of art in itself.
Flickr/MOTT
If you're spending the weekend in Stockbridge, you should definitely consider booking a room at the Red Lion Inn. It’s been operating continuously since 1773, which makes it one of the few inns in America that has welcomed visitors since before 1800.
Flickr/MOTT
The Stockbridge Bowl is a stunning scenic area full of outdoor opportunities.
You can paddleboard, kayak, canoe and swim to your heart's content.
Flickr/MOTT
One of the jewels of Stockbridge is the Berkshire Botanical Garden. It features 15 acres of vividly colored flowers, herb, vegetable and fruit gardens.
Flickr/MOTT
And don't forget to visit the blue steps at Naumkeag estate. They're a series of cascading pools that were originally built for an ambassador during the Gilded Age.
Flickr/MOTT

There’s so much to do and see in Stockbridge. If you want a more in-depth look at one of the town’s most beautiful attractions, check out our guide to the stunning Naumkeag estate.

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