Wilderness Road

The Wilderness Road was the major route for more than 200,000 people migrating west, at about the time the United States was coming into being. It provided a path for commerce in goods, livestock, and mail. In later years, some portions of the original Wilderness Road became paved routes for transportation arteries.

No less a figure than the legendary frontiersman Daniel Boone, DanielBoone was among some thirty-five men who were hired to clear a trail into Kentucky for the Transylvania Company in 1775. The company had obtained title to the route from the Cherokee and Iroquois, though not from the Shawnee, who attacked the party on March 24, 1775, killing some of its members. The rest regrouped and completed the trail.Wilderness Road

The trail looped for more than two hundred miles through Virginia, south into Tennessee, then north into Kentucky. Originally limited to foot or horseback traffic, it was further developed in 1792, when the Kentucky legislature funded improvements. Within four years, wagons began to carry families west to open up homes and businesses. Cabins built along the way served as the basis for future settlements.

Richard Henderson, of the Transylvania Company, hired Joseph Martin to open a land office in what is now Lee County, Kentucky, to help prospective settlers find land to settle. Martin’s Fort, built in this area of the Cumberland Gap, boosted Kentucky settlements by providing a connection back to Virginia and North Carolina. Business lifelines were strengthened in 1792, when part of the Wilderness Road stretching from Bean Station, Tennessee, through the Cumberland Gap in Virginia, to Danville, Kentucky, was designated as a postal route.

Old Wilderness Road, High Bridge, Kentucky, in about 1907.

(Library of Congress)

The road was abandoned around 1840, as other means of access were developed. Much of it was later incorporated into the routes of modern highways, linking the historical road that opened up much of the nation to commerce to the busy transportation arteries of the twentieth and twenty-first centuries.

The Wilderness Road continues to be an economic asset. In Virginia, the state tourism corporation has established a network of museums and other points of interest to visitors. In doing so, programmers have linked the historic Wilderness Road with other eighteenth century migratory paths, such as Great Road and Valley Pike. Virginia advertises the Wilderness Road as stretching from the city of Winchester, near the state’s border with West Virginia and Maryland, southward through Shenandoah, Rockbridge, and Botetourt counties, through the Roanoke and New River Valleys, and into the tip of western Virginia. Historians have disputed the accuracy of claiming all this as the Wilderness Road, but it remains an effective tourism marketing strategy. In any case, some 43 million Americans may claim descent from families that migrated along the road.

Further Reading

  • Green, Fess. Wilderness Road Odyssey: A Cyclist’s Journey Through Present and Past. Blacksburg, Va.: Pocahontas Press, 2003.
  • Kincaid, Robert L. The Wilderness Road. Whitefish, Mont.: Kessinger, 2007.
  • Williams, John Alexander. Appalachia: A History. Chapel Hill: University of North Carolina Press, 2002.


Cumberland Road

Homestead Act of 1862

Land laws

Mississippi and Missouri Rivers


First stagecoach line

Tennessee Valley Authority