Middlesboro Downtown Commercial District

Mt. Moriah Baptist Church is a historic church at 314 N. Main Street in Middlesboro, Kentucky. It was built during 1918-21 and added to the National Register of Historic Places in 1985.It is a brick building with brick laid in common bond.It was deemed significant as "The church building has played an important role in the history of the black community of Middlesboro and is a visible expression of the important role blacks have played in the settlement and later development of planned communities such as Middlesboro," which is the largest planned community in southeastern Kentucky.

The American Association, Limited, Office Building, at 2215 Cumberland Ave. in Middlesboro, Kentucky, United States, was built in c.1890. It was listed on the National Register of Historic Places in 1978.It is a two-and-a-half-story building, somewhat Richardsonian Romanesque in style.It was deemed "important historically because of its ties with establishment of the town. Its founder, Alexander Arthur, a Canadian, obtained British backing to form the American Association, Limited, that was to finance mining operations in southeast Kentucky and northeast Tennessee and the construction of Middlesboro, which was to serve as headquarters for these activities. The 2-1/2-story, brick structure was built as offices for the American Association, Limited."

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 (1.6 km) 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).

Middlesboro Mall is an enclosed shopping mall in Middlesboro, Kentucky, on U.S. Route 25E. It includes over 26 stores and services. Anchor stores are Belk and Roses.

The St. Mary's Episcopal Church in Middlesboro, Kentucky is a historic church located at 131 Edgewood Road. It was built in 1880 and opened for services in February 1881. It was added to the National Register of Historic Places in 1984.It is a wooden church which somehow escaped fires that destroyed most wooden churches of its era. It has a cross-shape within a 60 by 20 feet (18.3 m × 6.1 m) plan. Its NRHP nomination asserts:Saint Mary's Episcopal Church should be included on the National Register for two reasons. First, the church served as the religious home for wealthy British investors who worked to exploit the resources of the area in a large scale venture at the close of the 19th Century. Secondly, the church survives as one of the finest examples in Southeastern Kentucky of gothic revival architecture.

WMIK in Middlesboro, Kentucky, operates on an assigned frequency of 560 kHz with a daytime power of 2500 watts. Pre-sunrise and nighttime power are 500 watts and 88 watts respectively. The landmark radio studio is on the 19th Street Extension and Highway 441. The transmitting tower is situated one mile to the Northeast. WMIK signed on for the first time on Sunday, November 14, 1948, at 2 p.m. The Cumberland Gap Broadcasting Company, Incorporated, owned WMIK from 1948 until 1992. For many years, WMIK was the regional coverage leader, sales leader, and number one in the market for a vast majority of years as determined by the ratings company, Arbitron. The Cumberland Gap Broadcasting Company is no longer parent company of radio stations WMIK and its sister station WMIK-FM of Middlesboro, Kentucky. The Binghamtown Baptist Church through Gateway Broadcasting Corporation purchased both stations in October 1992. Both stations continue to serve the Cumberland Gap region twenty four hours a day with a mixture of local and nationally known ministers, Southern gospel music, and local programming. The Binghamtown Baptist Church Sunday morning worship service began broadcasting in the early 1950s and is one of the nation's longest consecutively airing church broadcasts.

The Middlesboro crater (or astrobleme) is a meteorite crater in Kentucky, United States. It is named after the city of Middlesborough (both spellings are used), which today occupies much of the crater. The crater is approximately 3 miles (about 5 km) wide and its age is estimated to be less than 300 million years (Permian). The impactor is estimated to have been about 100 m in diameter.

Middlesboro–Bell County Airport, (FAA LID: 1A6) is a city-owned public-use airport located 1 mile (1.6 km) west of the central business district of Middlesboro, a city in Bell County, Kentucky, United States.Although most airports in the United States use the same three-letter location identifier for the FAA and International Air Transport Association (IATA), this airport is assigned 1A6 by the FAA but has no designation from the IATA.

The Cumberland Gap National Historical Park is a United States National Historical Park located at the border between Kentucky, Tennessee, and Virginia, centered on the Cumberland Gap, a natural break in the Appalachian Mountains. The park lies in parts of Bell and Harlan counties in Kentucky, Claiborne County in Tennessee, and Lee County in Virginia. The park contains the Kentucky-Virginia-Tennessee tripoint, accessible via trail.The town of Cumberland Gap, Tennessee is located inside of the park's territory.The Cumberland Gap Visitor Center is located on U.S. Highway 25E just southeast of the city of Middlesboro, Kentucky, and just northwest of the Cumberland Gap Tunnel and the town of Cumberland Gap, Tennessee. The visitor center features a museum with interactive exhibits about the Gap's role as a transportation corridor, an auditorium that shows films about the area's cultural and natural history, a book store and the Cumberland Crafts gift shop with crafts from Appalachia.

Red Oak is an unincorporated community located in Bell County, Kentucky, United States.

Stony Fork Junction is an unincorporated community located in Bell County, Kentucky, United States.

The Cumberland Gap Tunnel is a dual-bore, four lane vehicular tunnel that carries U.S. Route 25E under Cumberland Gap National Historical Park near the intersection of Kentucky, Tennessee, and Virginia. The tunnel consists of two separate bores which carry four lanes of traffic between Cumberland Gap, Tennessee and Middlesboro, Kentucky. It is one of only two mountain vehicular tunnels in the United States that cross a state line, the other being the East River Mountain Tunnel on Interstate 77 and U.S. Route 52 between Virginia and West Virginia. The tunnel opened to traffic in 1996 and replaced a section of highway through the Cumberland Gap that had earned the nickname "Massacre Mountain" due to its hazardous design and high rate of traffic accidents.