Tollesboro is a western Lewis county town on KY 11 about 12 miles west of Vanceburg, named for the local Tolle family. It was incorporated as Tollsboro in 1860 and as Tollesboro in 1871. The corporation was dissolved in 1986. A White House post office operated in the area from 1839 to 1845 and was thereafter known variously as Tolesboro, Tolesborough, and Tollesboro.
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