The City of Middlesborough, Kentucky, (population 9,626) located in Southeast Kentucky in Bell County, is one of the largest communities in the Tri-State area. At the foot of the Cumberland Gap on the opposite side of the border from Tennessee and Virginia, Middlesborough has a storied past stretching from Daniel Boone, to an industrial boom in the 1890s, and a colorful story around bootlegging in the 20th century. 

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