Oak Hill is located on the plateau south of New River in Fayette County, elevation 1,961 feet. Settlement in the area began as early as 1820, and population grew rapidly after the building of the Giles, Fayette & Kanawha Turnpike by 1848. The turnpike served as the main street of Oak Hill, which is now located on modern U.S. 19 (Appalachian Corridor L).

Surrounded by the best farmland in the county, Oak Hill developed as a trading center for local farmers before the coming of the railroad. Then the construction of the White Oak branch of the Chesapeake & Ohio Railway, the completion of the Virginian Railway, and the mining boom in nearby Minden, Scarbro, and Whipple transformed Oak Hill into an important banking and regional trading center. Incorporated in 1903, the town's population accelerated in the early 20th century as a result of the coal industry. Oak Hill emerged as Fayette County’s leading urban center under the guidance of distinguished leaders such as businessman, banker, and coal operator Charles T. Jones, who with Albert G. Sevy advanced public education by establishing the town's first high school in 1902. In that year, James M. Ellis of Oak Hill became the second African-American elected to the West Virginia legislature.

From 1954 to 1977, Oak Hill was home to the popular Saturday Night Wrestling program, broadcast live weekly on WOAY-TV. Country music legend Charlie McCoy is a native of Oak Hill. It was also home to Marian Herndon McQuade, who campaigned to establish National Grandparents Day in the 1970s.

While most cities in southern West Virginia lost population as coal employment declined in the late 1900s, Oak Hill steadily grew throughout the century. The city’s population increased by more than 50 percent during the 1970s due in large part to the opening in 1977 of the nearby New River Gorge Bridge, completing Corridor L. The new highway and the popularity of whitewater rafting sparked a tourism boom and attracted new residents. A communications center, with a newspaper and radio and television stations, Oak Hill is the biggest city in Fayette County with a 2020 population of 8,179, the most in its history. As of 2020, Oak Hill was the 16th largest city in West Virginia.