Following the American Revolution, Americans began to migrate westward in large numbers. There was, however, a dispute over which states owned this land. The federal government encouraged the states to give up their claims within the Northwest Territory. Connecticut was one of the states with a claim to Ohio and, while giving up its right to most of the land, maintained its ownership of the northeastern corner of the territory, which became known as the Connecticut Western Reserve. The Connecticut Land Company was a group of private speculators who purchased approximately three million acres of the Western Reserve.

In 1796, the company sent one of its major investors, General Moses Cleaveland, to lead the survey of company lands within the Western Reserve. Cleaveland had served under General George Washington for several years during the American Revolution and rose to the rank of brigadier general in the Connecticut militia. In 1781, Cleaveland had opened a law practice in Canterbury, Connecticut, and also had served as a member of the Connecticut state convention that ratified the United States Constitution in 1788.

In all, there were a total of fifty-two people within Cleaveland’s surveying party, including two women. The surveyors mapped out a town along the eastern bank of the Cuyahoga River which they named Cleaveland. Because of a spelling error on the original map, the town of Cleaveland was spelled as Cleveland instead. The surveying party experienced many difficulties and did not complete as much work as had originally been expected, returning to Connecticut in the fall. Another surveying team went back to the Western Reserve the next spring, but without Cleaveland. Cleaveland never returned to Ohio, focusing the rest of his life on his legal practice and business interests back in Connecticut. He died in 1806.