Middlesboro is a home rule-class city in Bell County, Kentucky, United States. The population was 10,334 at the 2010 U.S. census, while its micropolitan area had a population of 69,060.It is located 1 mile west of the Cumberland Gap and is the largest city in southeastern Kentucky. It is located entirely between Pine Mountain and the Cumberland Mountains in the Middlesboro Basin, an enormous meteorite crater. The city claims to be the only one in the United States built entirely inside such a crater, as well as the home of ragtime music and the oldest continuously-played golf course in the country.