Webster County was drawn from land formerly in Stewart County in 1853. First named for a landmark creek, Kinchafoonee County, residents petitioned to change its name to honor orator and statesman Daniel Webster when visitors ridiculed the strange sounding name. The county seat, Preston, began as Mclntosh for General Lachlan Mclntosh of Revolutionary War fame. It's name was later changed to commemorate William O. Preston of South Carolina. The first Confederate flag-raising ceremony took place in front of the courthouse in Preston March 31, 1861.