The Pennington Gap Commercial Historic District encompasses the commercial core of the Lee County town of Pennington Gap, which historically served the local population as well as residents of the surrounding rural areas and nearby coal camps. Located at the lowest and flattest area of the Powell River Valley, Pennington Gap provided a natural access point to the rich natural resources in the surrounding region, particularly coal and timber in the northern section of the county. Initially platted by the Pennington Gap Land Improvement Company and chartered as a town in 1892, Pennington Gap developed around the Cumberland Valley Branch of the Louisville and Nashville Railroad. The approximately nine-acre district includes the active railroad line running through the center of the district, as well as the commercial, social, and entertainment resources constructed during the first three quarters of the 20th century. The one- and two-story masonry buildings comprising the town’s commercial core include small-scale stores and office buildings, a movie theater, a former social hall, two former automobile dealerships, and two former service stations. Architecturally, the buildings that comprise the Pennington Gap Commercial Historic District represent the evolution of the Commercial style throughout the 20th century and reflect the socio-economic character of a small working-class town in rural Appalachia.