Wilderness Road

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 (more northern route) 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.

In 1775, Daniel Boone blazed a trail for the Transylvania Company from Fort Chiswell in Virginia through the Cumberland Gap. It was later lengthened, following Indian trails, to reach the Falls of the Ohio at Louisville. The Wilderness Road was steep, rough and narrow, and could be traversed only on foot or horseback. By contrast, wagons could travel along the National Road route (originally the Braddock Road blazed by the competing Ohio Company and George Washington circa 1750), particularly after the improvements.

Despite the adverse conditions, thousands of families used the Wilderness Road. In 1792, the new Kentucky legislature provided money to upgrade the road. In 1796, an improved all-weather road was opened for wagon and carriage travel. The road was abandoned around 1840 (construction on the National Road after Vandalia, Illinois also stopping owing to the Panic of 1837 and early railroad construction), although modern highways follow much of its route.