Guilford is a town in New Haven County, Connecticut, United States, that borders Madison, Branford, North Branford and Durham, and is situated on I-95 and the coast. The population was 21,398 at the 2000 census. First settled in 1639 after being purchased from Native American leader Wequash, Guilford is considered by some to have the third largest collection of historic homes in New England, with important buildings from the 17th, 18th, and 19th centuries There are five historic house museums, including Dudley Farm and the Henry Whitfield House (1639), the oldest dwelling house in Connecticut and the oldest stone house in North America.
The Comfort Starr House (164546), is one of the oldest wooden framed private dwellings in Connecticut, and one of the few houses remaining of the original signers who settled Guilford. The northwest side of Guilford is flanked by the Metacomet Ridge, a mountainous traprock ridgeline that stretches from Long Island Sound to nearly the Vermont border. Notable features of the Metacomet ridge in Guilford include Totoket Mountain; its most notable peak, Bluff Head; and two eastern high points on the Totoket Mountain ridge named East Sugarloaf and West Sugarloaf. The 50-mile (80km) Mattabesett Trail traverses Bluff Head;, a shorter network of trails criss-cross the Sugarloafs. Guilford also contains the Westwoods Trail System which covers 39 miles (63km) of trails on 1,200 acres (4.9km2) of land.