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is the northernmost and least populous town of Fairfield County, Connecticut, United States. The population was 3,827 at the 2000 census. The town 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.
Sherman is the only town in Fairfield County with the 860 area code; the remainder of the county uses 203.
) its enrollment is about 450 students from pre-school to grade 8. There is no high school in Sherman; therefore students are given a choice of six high schools that Sherman will pay for them to attend (New Milford High School, New Fairfield High School, Brookfield High School, Henry Abbot Tech, Shepaug Valley High School, and Nonnewaug High School). The principal of Sherman School is Mary Boylan. The Sherman School was named amongst the top four schools in the State of Connecticut.