This area was inhabited long before Pickens County was officially formed in 1868. The land that is now Pickens County was home to the Cherokee when it was settled in 1743 by Cornelius Keith, a native of Scotland, and his family, who moved from Virginia to what is now the Oolenoy area and traded one of his ponies for land from the native Chief Woolenoy. (The Oolenoy area has been the site of the popular Pumpkin Festival each October since the 1970’s).

In 1791, the Washington District was formed by what is now Greenville, Anderson, Oconee, and Pickens Counties.

In 1798, the Pendleton District was formed by what is now Anderson, Oconee, and Pickens Counties.

In 1828, the Pickens District was made up of present-day Pickens and Oconee Counties.

In 1868, Pickens County and Oconee County were officially formed when each split from the Pickens District to form separate counties. The town of Pickens Courthouse (now referred to as Old Pickens) was relocated to the current site of Pickens. Several buildings were moved from Old Pickens to the new site of Pickens. The James E. Hagood House (now known as the Hagood-Mauldin House) is the only one of those buildings still remaining. It was the home of Frances Hagood Mauldin when she served as the Organizing Regent of the Fort Prince George chapter of the Daughters of the American Revolution (DAR) in 1920. The Hagood-Mauldin House is cared for by members of the Pickens County Historical Society. (One building still remains at the site of Old Pickens, and that is the Old Pickens Presbyterian Church.)