Top 9 Best Small Towns in Connecticut

  1. top 1 Mystic
  2. top 2 Chester
  3. top 3 Chaplin
  4. top 4 Kent
  5. top 5 Westport
  6. top 6 New Canaan
  7. top 7 Fairfield
  8. top 8 Old Saybrook
  9. top 9 Milford

Chaplin

Despite having a population of only 2,305, the natural beauty and historic charm of Chaplin, Connecticut, are unmatched. You'll enjoy strolling through the charming historic district, exploring the peaceful hiking trails, and soaking up the relaxed pace of life. The Connecticut town of Chaplin exudes a timeless New England charm. This adorable little town, founded in the 18th century, is full of historical artifacts. Benjamin Chaplin, who passed away in 1795 and left money to build a church close to his former home, is credited with giving the town its name. Spend some time exploring the Chaplin Historic District before venturing into the nearby wilderness.


Beautiful structures like the former William Ross Public Library can be found as you stroll through these calm streets. It was founded in 1828 when the Goodell Lincoln General Store first opened. Visit the Chaplin Museum at 1 Chaplin Street if you enjoy history. Despite its diminutive size, this unusual location is packed with information. Take a stroll on the Two Sisters Trail for a peaceful and simple hike. This 1.3-mile hiking trail meanders through thick forests, giving you the impression that you are far from civilization. Without going to Diana's Pool, a trip to Chaplin isn't complete. Nothing beats a cooling swim in the ocean when it's hot outside. Naturally, this region is beautiful all year round. You'll be welcomed by exceptional foliage in the fall. The Natchaug River sparkles with frosted beauty in the winter. Go to the sleepy Connecticut town of Chaplin if you need some quiet time.

Photo by 12019 on Pixabay
Photo by 12019 on Pixabay
Photo by 12019 on Pixabay
Photo by 12019 on Pixabay

Top 9 Best Small Towns in Connecticut

  1. top 1 Mystic
  2. top 2 Chester
  3. top 3 Chaplin
  4. top 4 Kent
  5. top 5 Westport
  6. top 6 New Canaan
  7. top 7 Fairfield
  8. top 8 Old Saybrook
  9. top 9 Milford

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