In 1774, Colonel William Preston gave orders to Captain Billy Russell to warn settlers and surveyors in Kentucky of an Indian upraising.

In May, 1779, the Virginia Assembly enacted a law opening Kentucky to general settlement by survey, entry, and residence. In the same year, the General Assembly of Virginia passed an act for marking and opening a road over the Cumberland Mountains in the County of Kentucky. Richard Calloway and John Kinkead effected the opening of the road* by Dec 1, 1781.

From 1800 to 1810, each year brought a large number of families. Grants under the “Headrights” provision were made to the following… Matthew and William Smith

* (Wilderness Road – from Wikipedia)

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 and rough, 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.