Sherman

About Sherman

Tucked into the northwestern corner of Fairfield County, Sherman is a beautifully rural escape that somehow feels worlds away from the city — even though New York is just 62 miles down the road. With rolling hills, quiet lakes, and a genuine small-town pace, it's the kind of place where weekenders quickly start wondering why they don't just stay for good. Sherman is Fairfield County's northernmost and least populous town, and its residents wouldn't have it any other way.

What to Know

• Candlewood Lake, Connecticut's largest lake, borders Sherman to the west, offering boating, fishing, and swimming that draw visitors year-round.
• About a third of Sherman's residents are weekenders — New Yorkers who've claimed a slice of Connecticut countryside as their sanctuary.
• The town is served by Region 1 School District, which provides a close-knit educational community across several small northwestern Connecticut towns.
• Sherman sits within the Western Connecticut Planning Region, connecting it regionally with neighboring towns like New Milford and Kent.
• The Appalachian Trail passes through nearby towns, making Sherman a natural base for hikers exploring this iconic stretch of New England wilderness.

History

Sherman was carved out of New Fairfield and incorporated as its own town in 1802, named in honor of Roger Sherman — the only Founding Father to sign all four of America's great state papers, including the Declaration of Independence. Its 1886 Town Hall still stands as a proud symbol of the community's enduring character.

Community & Living

Sherman has the soul of a classic New England village — unhurried, neighborly, and deeply connected to its natural surroundings. Residents cherish the lack of commercial sprawl and the sense that nature is always just a few steps out the door. It's a community where people choose to be, and that intentionality shows.