Sherman is the northernmost and least populous town of Fairfield County, Connecticut, United States. The population was 3,581 at the 2010 census. The town was formed in 1802 from the northern part of New Fairfield. It is named for New Haven's Founding Father, Roger Sherman. 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 State Park is in the town. 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.