Cortland County is located in the glaciated Appalachian Plateau area of Central New York, midway between Syracuse and Binghamton. This predominantly rural county is the southeastern gateway to the Finger Lakes Region. Scattered archaeological evidence indicates three different aboriginal cultures hunted the area beginning about 1500 A.D.

What was to become Cortland County remained within Indian territory until the American Revolution. It became part of the Military Tract, when in 1781, more than 1 1/4 million acres were set aside by the State's Legislature to compensate two regiments formed to protect the State's western section from the English and their Iroquois allies, at the close of the Revolution. To encourage settlement in the upstate isolated wilderness, the State constructed a road from Oxford through Cortland County to Cayuga Lake in 1792 through 1794. This, and construction of privately financed roads, were the major impetus to settlement.