According to legend, it was named for "Free Charles" who was named Charles Wilson, a former slave, once owned by Ben Wilson. Charles had owned a tavern on the trail leading from Caldwell County to Madisonville. Thomas Green Chapell, allowed Charles to operate his tavern, which at that time was merlyy a lodge and bar, on his property. Isabelle Bishop, wife of William, freed her house maid in 1852 so her and Charles could wed. "BlackMaria" was the name she was called. Her and Charles bore 5 children, one including "Uncle Aaron" a local elderly man living in Charleston his whole life from 1871-1969.
In 1902 a school was needed for the board of education of [[Wikipedia:Hopkins County|Hopkins County]], Thomas Green Chapell saw that land and building was given. Charleston School was first a one-room school house 1902-1931 and then built by the CCC during the depesstion a large school with gym was constructed. Thisd served the community well until 1990.
In 1935 a Baptist church was organized by James Workman and 25 charter members. I.N. Workman being one of them and serving as deacon from 1935 until his death in 2013.
A Charleston post office was in operation from 1855 to 1909. Other businesses included: Charles' Tavern 1852-1891, Franklin Store 1866-1970, Dawson Daylight Coal Inc., Workman Mines 1921-1931.
[[Wikipedia:Ila Earle Fowler|Ila Earle Fowler]], writer and poet, daughter of local physician Dr. Benjamin Prince Earle
[[Wikipedia:Dottie Rambo|Dottie Rambo]]' Gospel singer and song writer
Origin of Town Name
This is from an article about the origin of town names in Hopkins County is from the City Desk Column by Ernest Claytor in the Madisonville Messenger; Madisonville, Kentucky; November 7, 1949..........
Charleston-At this place, in the olden time, there was a tavern kept by a Black Man named Charles or Free Charles,from whence this place took the name of its post office. --Dlbradley1 14:06, 30 July 2008 (EDT)