Pikeville (population 6,295) was founded in 1824 as the seat of Pike County and became the trading center for area farmers. During the Civil War, the community was occupied by the Union Army and was a center of Federal operations in Eastern Kentucky.
Following the war, the community grew in size and prosperity, with a great increase in commerce following arrival of the railroad in 1905. The railroad made it profitable to mine Pike County's coal, and Pikeville became a coal shipping and distribution center.
The first half of the 20th century saw a building boom in the community, and many of these historic buildings are included in Pikeville's five historic districts that are listed in the National Register of Historic Places.
Original C&O Railroad buildings and a historic railroad car now house the Pikeville-Pike County Tourism Commission, the Pike County Chamber of Commerce, and the Big Sandy Heritage Center.
Among the historic sites that visitors are encouraged to visit are several associated with the Hatfield-McCoy Feud. This notorious fight between two families in the 1880s gained national publicity and helped to create an enduring stereotype of the "hillbilly."
The Hatfield-McCoy Driving Tour directs visitors to sites near Pikeville associated with the feud, and the city recently made improvements and installed interpretive signage at the Dils Cemetery, the final resting place of several key players in the feud. The annual Hatfield-McCoy Festival helps visitors to better understand the feud and the overall history of the area.
Designated a Preserve America Community in April 2005.