As early as 1800, a developer built a road into the interior of the town, and then disposed of two thirds of the land in less than four years. He kept a list of the purchasers, which forms the basis for our list of pioneers.

Rutland lies just east of the city and Town of Watertown, south of the Town of Le Ray and, west of the Town of Champion, and borders the Fort Drum military reservation. Its southern border is with Lewis County. The Black River flows along its northern border which, at first, supported grist and lumber mills at places whose names later became Felts Mills and Black River. Settlers in the northern part of the town could, from a high place, "look away south to the Rutland Hills."

Populated areas within the town include Rutland Center, Tylerville (South Rutland), and Felts Mills. The Southern part of the Village of Black River, south of the Black River, lies within the town.