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 is part of the Western Connecticut Planning Region. 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.

New Milford is a town in Litchfield County, Connecticut, United States. The town, part of Greater Danbury, as well as the New York Metropolitan Area, has a population of 28,115 as of the 2020 census. New Milford lies 14 miles (23 km) north of Danbury on the banks of the Housatonic River, and shares its border with the northeastern shore of Candlewood Lake. It is the largest town in the state of Connecticut in terms of land area at nearly 63.7 mi2 (164.9822 km2). The town center is listed as a census-designated place (CDP).