Middlesboro, Ky is located on the Kentucky side of Cumberland Gap, close to the  Cumberland Gap National Park, which borders 3 states Kentucky, Tennessee and Virginia.  Population 10,384. Middlesboro is the home of the Middlesboro Country Club with one of the oldest 9 hole golf courses in the country established in 1889. Middlesboro is also the home of the ACTOR LEE MAJORS.                                                                                                                                06/24/2009