Gaylordsville is a village (neighborhood/borough) in the northwest corner of the town of New Milford, Litchfield County, Connecticut, United States.

His great-grandson, Ensign William Gaylord, moved to Woodbury in 1706 and married Joanna, the daughter of Captain John Minor.

To ensure the good will of the Native Americans living in the area, he also bought it from them, giving, according to legend, a horse, a mule, and a two-wheeled cart.

The following year his oldest son, Aaron, built a house about a quarter of a mile south of his father's, and on the west side of the valley.

During this time the Gaylord family became good friends with their Indian neighbors, teaching them better methods of agriculture[citation needed], and dickering with them for furs they could use.

The southern boundary is also vague, usually considered to be an imaginary line leaving the Housatonic River somewhere south of the Tory Cave and extending across Squash Hollow.

The Housatonic River runs through the center of the village and is joined by the Wimisink, Womunshenuck, Naromiyocknowhusunkatankshunk (Morrissey), and Squash Hollow brooks.