11 Most Adorable Small Towns In America

Photo by James Kirkikis at Shutterstock



This Berkshire town probably looks familiar because you’ve seen it depicted in Norman Rockwell paintings. This town hits three charm standards: architecture, nature, and culture, but most importantly, for a small town whose population is just under 2,000, there are cultural events year-round.

What To See And Do:

  • The Housatonic River canal runs through downtown, where galleries and shops along Main Street feature everything from contemporary glass to Victorian-era antique jewelry. It’s typical small-town America at its finest.
  • The Norman Rockwell Museum.
  • America’s longest-running international dance festival.
  • Stockbridge Main Street at Christmas.
  • An entire weekend in early December includes house tours and vintage cars.

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