Sherman is the northernmost and least populous town of Fairfield County, Connecticut, United States. The land which is now called Sherman was formerly occupied primarily by native people of Algonquian lineage. The town was formed in 1802 from the northern part of New Fairfield. It is named for Roger Sherman, the only person who signed all four founding documents of the United States of America. He also had a cobblers shop in the north end of town which has been reconstructed behind the Northrup House in the centre of town. Sherman has been named "Best Small Town in Connecticut" three times by Connecticut Magazine. The Appalachian Trail goes through the northern end of Sherman. Part of Squantz Pond is in the town. Sherman is a popular weekend retreat for New York City residents, with about a third of its residents week-enders. Sherman has one area on the National Register of Historic Places: the Sherman Historic District, bounded roughly by the intersection of Old Greenswood Road and Route 37, north-east past the intersection of Route 37 East and Route 39 North and Sawmill Road. The district was added to the National Register in 1991.
Sherman has a population of over 3,581 people.