Pikeville was the site of the first permanent European settlement in Pike County. The town was established by the state legislature to be the seat of Pike County in 1824 and was formed from land owned by Elijah Adkins.

The town experienced slow development through- out much of the 19th century, primarily relying on steamboat navigation of the Levisa Fork for com- mercial transportation. The 1830 census reported that there were 49 residents living in Pikeville. In 1840, the majority of residents were farmers, with others employed as carpenters, laborers, black- smiths, merchants, and lawyers.

The arrival of the Chesapeake & Ohio Railroad in 1905 opened the Eastern Kentucky coalfields to development. Between 1905 and 1950, the mineral extraction underway in the county brought finan- cial resources to Pikeville in the form of industry, businesses, and amenities. As the company towns shrank or disappeared, Pikeville continued to anchor commerce and related social affairs in the county.