Prestonsburg is a city in and the county seat of Floyd County, Kentucky, United States. It lies in the eastern part of the state, along the banks of the Levisa Fork of the Big Sandy River. It was founded in 1797 by Col. John Preston—for whom it was named—along with Solomon Stratton, Matthias Harman and Andrew Hood. The population was 3,255 at the 2000 census.
The Country Music Highway runs through Prestonsburg and celebrates the region's rich heritage of music. Country music stars including Loretta Lynn, Wynonna Judd, Naomi Judd, Billy Ray Cyrus, Tom T. Hall, Ricky Skaggs, Keith Whitley, Dwight Yoakam, and Patty Loveless are all from the Big Sandy Valley. Heavy Metal singer and guitarist Dave Reffett also grew up near this area.
Prestonsburg is mentioned in Dwight Yoakam's "Readin', Rightin', Rt. 23" (from his album Hillbilly Deluxe), a song about the yearning of local coal miners to escape their plight by traveling up U.S. Route 23 to find employment in the factories in the North, not knowing that they were only trading one miserable life for another.