Historical Marker #510 in Letcher County notes the history of Pound Gap, a natural pass in the Appalachian/Pine Mountain range.
Early explorers moving west looked for natural passes through the rugged Appalachian Mountains. Many of these passes were marked by centuries-old trails, made first by animal herds of buffalo and elk, and later used by Native Americans. These trails led through the paths of least resistance and thus utilized natural gaps in the mountain ridges. Like Cumberland Gap to the south, Pound Gap, on the Virginia-Kentucky state line, was an early entry point for pioneer explorers and settlers.
In 1751, surveyors for the Ohio Company, including Christopher Gist, explored through Pound Gap. For the next several decades, hunters including Daniel Boone used Pound Gap as an entry point into Kentucky. By about 1800, pioneer settlers, especially from the western counties of Virginia, made Pound Gap their main point of entry in addition to Cumberland Gap.
In 1834, the Kentucky legislature allocated funds to improve the road from Mount Sterling to Pound Gap. This enhanced thoroughfare allowed Kentucky farmers to move their herds of livestock to multiple southern markets.
During the Civil War, Pound Gap was used by both Union and Confederate armies. In March 1862, General (and future president) James Garfield reported, "Just returned from a 4 day expedition to Pound Gap. Took 600 infantry and 100 cavalry. On 16th attacked 500 rebels under Maj. J. B. Thompson intrenched at Pound Gap on summit of Cumberland Mountains. Fight lasted less than 20 minutes, rebels totally routed. They abandoned everything." In 1864, during a raid toward central Kentucky, Confederate cavalry under John Hunt Morgan forced a small Union detachment from Pound Gap. Later, Morgan used the gap as an evacuation route out of the state.
Today, US Highway 23 runs through Pound Gap. The natural beauty of the mountains of eastern Kentucky and southwestern Virginia are enjoyed by thousands of travelers who pass through this historic gateway every day.