[1] Chocchuma and Chickasaw Indians first occupied the territory and had a village at Old Town.

Orr described the "aspiring little city" as the "head of navigation on the Loosa Scoona river from which many keel boat bore hundreds of bales of cotton to New Orleans.

There was a post office, a store, and a pottery which made plates, bowls, and churns.

Calhoun County was organized in 1852, and the first courts and meetings of the Board were held at Old Town.

That same year, the first meeting of the Board of Supervisors was held in the Methodist Church, and it was decided to move the county seat to Pittsboro.