Middlesboro (locally ) 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 (one of three known astroblemes in the state). 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.
Originally funded by English businessmen, the town opened its first post office on September 14, 1888, under the name Middlesborough, presumably in honor of the English town of - at the time - the same name. The city was formally incorporated under that spelling on March 14 two years later, but the post office switched to "Middlesboro" in 1894 and that spelling has since been adopted by the city itself, the city's school district, the Kentucky Land Office, and the U.S. Board on Geographic Names. Some still contend "Middlesborough" remains official, however.
The area was originally inhabited by American Indians such as the Shawnee. The first European known to have visited the area was Gabriel Arthur in 1674. He was later followed by Thomas Walker in 1750 and Daniel Boone in 1769.
John Turner of Virginia established the settlement of Yellow Creek nearby in 1810, but the town did not begin to develop until the Scottish-born and Canadian-raised engineer and entrepreneur Alexander Arthur took an interest in the Yellow Creek Valley. Having settled in Knoxville, Tennessee, he arranged development projects in the area as part of the post-war New South. Taking an interest in the iron deposits around the Cumberland Gap around 1886, Arthur was able to convince some of the wealthy scions of Gilded-Age Asheville, North Carolina, to talk to their families about funding a "Pittsburgh of the South", but sufficient financing was not forthcoming.