The Wilderness Road was one of two principal routes used by colonial and early national era settlers to reach Kentucky from the East. Although this road goes through the Cumberland Gap into southern Kentucky and northern Tennessee, the other is sometimes called the "Cumberland Road" because it started in Fort Cumberland in Maryland. Despite Kentucky Senator Henry Clay's advocacy of this route, early in the 19th century, the northern route was selected for the National Road, connecting near Washington, Pennsylvania into the Ohio Valley of northern Kentucky and Ohio.

The Cumberland Gap is a pass in the eastern United States through the long ridge of the Cumberland Mountains, within the Appalachian Mountains and near the tripoint of Kentucky, Virginia, and Tennessee. At an elevation of 1,631 feet (497 m) above sea level, it is famous in American colonial history for its role as a key passageway through the lower central Appalachians.