city, Bell county, southeastern Kentucky, U.S., about 61 miles (98 km) north of Knoxville, Tennessee. It lies in a valley (believed to have been formed by a meteor crater) at the western end of the Cumberland Gap near where the borders of Kentucky, Tennessee, and Virginia meet. Despite its location on the old Wilderness Road through a natural pass in the mountains, the site was not settled until 1889. It was developed by British investors as an iron and steel centre and named after Middlesbrough, Yorkshire, England. Their company went bankrupt, however, when the London bank Baring Brothers (Baring family) and Company failed, resulting in the financial Panic of 1893. The city eventually recovered as a centre for the important eastern Kentucky coalfields.

Modern industries include tanning, food processing, and the manufacture of plastic pipe, elastic webbing, and apparel. The oldest continuously played golf course in the United States is located there, and the city is a tourist gateway to Cumberland Gap National Historic Park to the east. Kentucky Ridge State Forest is north, and Fern Lake, with a wild-game sanctuary, is south. Middlesboro is home to Southeast Tech (1995), a two-year liberal arts and technical school. Inc. 1890. Pop. (1990) 11,328; (2000) 10,384.