Hillsboro is an unincorporated community in Fleming County, Kentucky, United States. Hillsboro is located at the junction of Kentucky Route 111 and Kentucky Route 158, 9.8 miles south-southeast of Flemingsburg.First called Foudraysville for the Foudray family of early settlers, it was renamed Hillsboro when the post office opened in 1833.Hillsboro Covered Bridge, which is listed on the National Register of Historic Places, is located in Hillsboro.