The Wilderness Road was the principal route used by settlers for more than fifty years to reach Kentucky from the East. In 1775, Daniel Boone blazed a trail for the Transylvania Company from Fort Chiswell in Virginia through the Cumberland Gap into central Kentucky. It was later lengthened, following Native American trails, to reach the Falls of the Ohio at Louisville. The Wilderness Road was steep, rough, narrow, and it could only be traversed on foot or horseback. Despite the adverse conditions, thousands of people used it.

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, although modern highways follow much of its route.