The City of Middles is situated in the calm splendor of the magnificent Appalachian Mountains at the southern portion of the Cumberland Gap in southern Kentucky near the Virginia state line. It was the area’s stunning surroundings that initiated the creation of Middles. In the middle of the 19th century, many mountain resort towns were being constructed all over the country to cater to wealthy European visitors – this was no exception as the first structure that was built in the area that would become Middles was a mountain resort complex.

It was towards the turn of the 20th century that iron deposits were found in the area. Buoyed by the prospect of immense wealth generated from iron mining, the area’s authorities named the area Middles after the English mining town. Unfortunately for the fortunes of area residents, the iron was extremely difficult to recover and was no economically feasible to mine. Fortunately, large coal deposits were discovered and the coal mining industry became the backbone of the local economy throughout the 20th century.

Today, Middles continues with some mining activities but efforts have been made to expand their economic base. Tourism has great potential in the area due to the city’s location and close proximity to the expansive Cumberland Gap National Historic Park, Kingdom Come State Park, and Pine Mountain State Resort Park.