Berkshires Town Makes List of America’s Most Beautiful Small Towns

We know there’s definitely a lot of beauty when it comes to Massachusetts. We’re spoiled compared to a lot of states. But especially on the west side of the state, the Berkshires can hold their own against most places. For those who listed the “Most Beautiful Small Towns in America”, one of the towns in the Berkshires was on this exclusive list.

When I first moved to the Berkshires, I remember talking on the phone with my brother, who lives in the Midwest. I said to him, “I have never seen a place like this. Apparently another publication agrees. The publication, ‘Architectural Summary‘ recently listed the “55 Most Beautiful Small Towns in America”, and as mentioned, the only Bay State town that made the list is in the Berkshires? So where is he?

If you’ve already figured it out from the photos, then you know we’re talking about Stockbridge, MA. Here’s what ‘Architectural Digest’ had to say about its list as one of ‘America’s Most Beautiful Small Towns’:

If this Berkshires town sounds familiar, you’ve probably seen it in Norman Rockwell’s paintings. A canal (the Housatonic River) runs through downtown, where shops and galleries along Main Street (the subject of Rockwell’s 1967 painting Main Street, Stockbridge at Christmas) feature everything from antique Victorian jewelry to contemporary glass. This city meets all three indicators of beauty: architecture, nature and culture, including the Norman Rockwell Museum. And, most importantly, for a small town (population just under 2,000) there are cultural events throughout the year, ranging from the oldest international dance festival in America (Jacob’s Pillow, mid-June to late August) and Stockbridge Main Street at Christmas (a full weekend in early December that includes vintage cars and home tours). It’s the epitome of small town America in its heyday.

What’s not to love about all of this?

As you can see, and perhaps you have already experienced, the small town vibe is definitely present throughout the town of Stockbridge. And as you can also see from the photos, autumn seems to be an ideal season to spend a weekend there. After all, it’s one of the prettiest small towns in America, and it’s right here in the Berkshires!

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