Gaylordsville, CT

Gaylordsville is a village in the northwest corner of New Milford, Connecticut, stretched along the Housatonic River between Long Mountain and the Sherman town line. The valley runs roughly four miles north to south and about a mile across, with the river joined by several brooks before the landscape tightens around the Straits. That geography gives Gaylordsville a shape you can read from the road: water through the middle, mountains at the edges, and old settlement sites gathered along the level ground.

ATTRFrancis Luis Mora / CC0

The Gaylord family set the local story in motion. William Gaylord came north from New Milford in the 1720s, built a cabin and then a frame house, and began clearing fields in the valley. A one-room schoolhouse followed by 1740; after it closed in 1967, residents preserved it as the Little Red Schoolhouse, now maintained as a museum by the Gaylordsville Historical Society. The Housatonic Railroad reached the village in the 1840s, adding a station and another way for the valley to connect outward. Gaylordsville remains part of the New Milford School District, with its history gathered around the river, the schoolhouse, the old road, and the family name.