Webster County, established in 1853, drew lands from Lee and Stewart counties. Although residents originally knew the county by its Creek name, Kinchafoonee, they eventually grew tired of visitors' ridicule of the curious sounding word and so, in 1856, petitioned to change the county's name to honor orator and statesman Daniel Webster.
The county seat, Preston, remembers South Carolina senator William Preston. The first Confederate flag-raising ceremony took place in front of the county courthouse in Preston on March 31, 1861. At the end of the Civil War, Union troops cut down and destroyed this flagpole.