The Middlesboro Downtown Commercial District in Middlesboro, Kentucky is a  historic district which was listed on the National Register of Historic Places in 1983.

It is roughly bounded by Cumberland Ave., 19th Street, 20th Street, and Edgewood Road.  It included 61 contributing buildings, including a post office.

It includes the original downtown core.

Contributing buildings include:
Old City Hall
the Coal House, "now the Chamber of Commerce, which is built entirely of coal"(!)
the United States Post Office (1915), Classical Revival in style
the old Carnegie Library, a one-story classical masonry structure
the First Presbyterian Church, built in 1889 and expanded in 1912.

Description 
Middlesboro is located in the southeastern part of Bell County, serving as a prominent trade center for a tri-state area. It lies at the western entrance of the Cumberland Gap, bordered by Harlan County, Kentucky, and Lee County, Virginia to the east, Claiborne County, Tennessee to the south, and Whitley, Knox, and Clay Counties in Kentucky to the west and north.

The Middlesboro Commercial District encompasses the historic downtown area, planned in 1888. This district comprises commercial, governmental, and ecclesiastical buildings constructed from the late 19th century to the early 20th century. The district comprises segments of Cumberland Avenue, 19th Street, 20th Street, as well as Lothbury and Englewood Streets.

Cumberland Avenue serves as the primary commercial street in Middlesboro, characterized by two and three-story load-bearing masonry buildings. Most of these buildings remain intact, although some minor cosmetic alterations have been made over the years. One notable structure is the Campbell Building, dating back to 1890, which showcases exemplary late 19th-century commercial architecture and retains its original storefront.

The intersection of Cumberland Avenue and 20th Street within the Middlesboro Commercial District showcases an intriguing focal point known as the "town center." The buildings facing this intersection are set back from the main building line, creating a modified plaza or town square ambiance. Although a statue that once stood at the center of the intersection has vanished, the imposing buildings surrounding it, including the Old People's Bank Building, Ball Brothers Furniture Store with its striking terracotta design, J.C. Penny Building, and Catos Building, contribute to the vibrant town center atmosphere. These buildings are thoughtfully arranged in an L-shaped configuration to enhance the overall effect.

The district's western and partial northern boundaries are defined by the historic city canal, originally built around 1890 to provide fresh water to the town. Some remnants of the canal's wooden planks can still be found. The city is currently seeking funding to restore the canal, envisioning its transformation into a city park. Located near the western boundary on Cumberland Avenue, the American Association Building, listed on the National Register, stands as a testament to the district's architectural heritage.

On the northern edge of the district, the canal runs behind the commercial structures along Cumberland Avenue, extending up to 20th Street. 20th Street serves as a major north-south intersection within the district and is home to notable buildings such as the Old City Hall, the Coal House (now housing the Chamber of Commerce and constructed entirely of coal), and the classical revival-style United States Post Office, completed in 1915. Among the distinguished buildings lining 20th Street, you will find the old Carnegie Library—a one-story classical masonry structure—and the First Presbyterian Church, which was originally constructed in 1889 and underwent expansion in 1912.

References

Historic districts on the National Register of Historic Places in Kentucky
National Register of Historic Places in Bell County, Kentucky
Late 19th and Early 20th Century American Movements architecture
Middlesboro, Kentucky