The great emigrant trail leading from southwestern Virginia through the Cumberland Gap into central Kentucky was known as the Wilderness Road. The trail was first marked by Daniel Boone in March, 1775, and for this reason was often called Boone's Trace. As early as 1769, Boone had penetrated into the Kentucky country for hunting and exploration and in the following years he became thoroughly familiar with the region beyond the mountains. In 1775, Col. Richard Henderson, who had just purchased a great tract of land in Kentucky for his Transylvania Company, employed Boone to lead a party of settlers to the Kentucky River. The route followed was an extension of the Virginia Path which led from Pennsylvania through the Shenandoah valley into the Carolinas. Previously a branch had led from the Virginia Path near present-day Wytheville, Virginia, southwest to the Watauga settlement in Eastern Kentucky. From Fort Watauga Boone blazed a trail west along the Virginia-Tennesse boundary through the Cumberland Gap, then north about 50 miles along the Warriors path -- a trail through eastern Kentucky over which traveled war parties in conflicts betwen the northern and southern Indian tribes -- and then west along a buffalo trace to Rockcastle River , up Roundstone Creek, through the gap in Big Hill, and down Otter Creekto the site on the Kentucky River where the outpost of Boonesboro was constructed.
At first this trail was little more than a footpath, but in 1779 the Virginia legislature passed an act providing for the improvement of the Wilderness Road in order to prevent the western settlements from falling under British influence. Yet little was done to improve the road until after Kentucky became a state in 1792. Some improvements were authorized in 1795 and 1797. Even so, the route was little more than a pack road until 1818 when steps were taken to widen and improve it. It was one of the two great emigrant routes to the West, the other being the Ohio River. US Highway 25 was laid out along the route of the Wilderness Road.