Fountain Run was originally called "Jamestown". The order establishing Jamestown on of land owned by Jacob Goodman Sr. was entered in
Barren County Court Order Book #4 during November Court, 1816. Jamestown, located in
Monroe County after 1820, appears in public records and on maps with this name through the
Civil War. The name was changed to "Fountain Run" for the new post office (1856) because of
Jamestown, already established as the county seat of
Russell County. Fountain Run was formally incorporated by the
state legislature in 1908. Although not historically recorded as such, the name "Fountain Run" is traditionally believed to refer to the town's spring and stream branch, perhaps reminiscent of
"run" as a name for streams in
colonial Virginia. "Jimtown" (diminutive of Jamestown) as a nickname for the town and community persisted after the new postal name of "Fountain Run" was created. For example, the "Glasgow and Jimtown turnpike road" was authorized by an act of the Kentucky Legislature (Chapter 906), February 17, 1866, as a toll road between Glasgow and Fountain Run via currently marked
Kentucky Route 249, Kentucky Route 921, Defeated Creek Road, and
Kentucky Route 87—see the 1879 Barren County map which reveals the most improved route of that era. This new toll road followed the route of the old "[Thomas] Flippin road" (est. 1799) to Dry Fork—Kentucky Route 249 today, then turned at the intersection to proceed via the current route of Highway 921 to Defeated Creek Road. The act also provided for a toll road branch that continued from Dry Fork via the Flippin road (a.k.a. Pikesville road after 1818) toward the "forks of Indian Creek"—also Kentucky Route 249 as straightened and improved, today. This incorporated toll road and its branch road later reverted to public roads maintained by the local magistrates, but
Kentucky Route 249 retained its moniker as the "Jimtown Road" well into the 20th century. Today, this route from Glasgow to Flippin and Fountain Run is more commonly known as the "Roseville Road". Famed musician
Billy Vaughn from Glasgow, Kentucky composed (1968) the song, "The Jimtown Road", inspired by this historic Barren County route, which was recorded (1969) by
The Mills Brothers, although the song's lyrics are mostly veiled references about Glasgow and
Bowling Green, Kentucky, instead of Fountain Run. Jimtown Academy was established in 1897 in Fountain Run as a school of private instruction that included "primary and preparatory departments", with W. B. Robinson as principal. Fountain Run elementary and high schools were also located here until consolidated. The Monroe County section of
Kentucky: A History of the State (1886) includes brief biographies of some prominent 19th-century citizens of the Fountain Run community. Two booklets authored by local resident Lucy Albright (1903–1985) have been widely recognized as sources of the traditional history of Fountain Run and of genealogies of some early families of the community. Histories of Monroe County that include this community have been more recently published. ==Geography==