Wilderness Road, principal avenue of westward migration for U.S. pioneers from c.1790 to 1840, blazed in 1775 by the American frontiersman Daniel Boone and an advance party of the Transylvania Company. Feeders from the east (Richmond, Va.) and the north (Harpers Ferry, W.Va.) converged at Fort Chiswell in the Shenandoah valley. Boone's road ran southwest from there through the valley, then W across the Appalachian Mts. and through Cumberland Gap into the Kentucky bluegrass region and to the Ohio River. The road followed old buffalo traces and Native American paths, but much of it had to be cut through the wilderness. In the early years, many travelers fell victim to hostile Native Americans.
After Kentucky became a state in 1792, the road was widened to accommodate wagons. Private contractors, authorized to keep up sections of the road, charged tolls for its use. With the building of the National Road, the Wilderness Road was neglected and finally abandoned in the 1840s. Since 1926 the Wilderness Road has been a section of U.S. Route 25, the Dixie Highway.