Chaplin

Chaplin, Connecticut is Windham County’s best-kept secret — a historic New England town where timeless charm and elevated countryside living meet. With just over 2,100 residents, this intimate community is rooted in 18th-century heritage and defined by its serene landscapes, iconic architecture, and rich sense of place. From the preserved elegance of the Chaplin Historic District to the natural beauty of Diana’s Pool and the surrounding state forests, every detail evokes a lifestyle of peace, purpose, and authenticity. Winding roads, vibrant local institutions, and a deep connection to the land make Chaplin more than a destination — it’s where legacy lives, and life slows down in the best way.