Sherman is the northernmost and least populous town of Fairfield County, Connecticut, United States. The population was 3,527 at the 2020 census. 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 center 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 weekenders. The town is located northeast of New York City, making it part of the New York metropolitan area. 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, northeast past the intersection of Route 37 East and Route 39 North and Sawmill Road. The district was added to the National Register on August 31, 1991. Sherman is the only town in Fairfield County in the 860 area code; the remainder of the county is served by the area code 203/area code 475 overlay. History The land which is now called Sherman was formerly occupied primarily by native people of Algonquian lineage. In 1724, colonial settlers from Fairfield, Connecticut, received approval from the General Assembly of the Colony of Connecticut to establish a new township. According to one account, they negotiated with Chief Squantz of the Schaghticoke tribe. Alternatively, it is told that they did not negotiate with Chief Squantz because he moved to the north end of Squantz Pond land area and refused to "sell" the township of New Fairfield. They returned in the spring of 1725, but found that Chief Squantz had died during the winter. His four sons and heirs refused to sign the deeds. It was not until four years later that the white men called "The Proprietors" finally got the drawn marks of several other native people who may not have had authority to sell the land. They "purchased" a 31,000-acre tract of land that is now New Fairfield and Sherman, for 65 pounds sterling, the equivalent