The Wilderness Road
Migration to Kentucky
In 1763, the King of England by proclamation had forbidden surveys or patents of land beyond the head waters of the streams which ran to the Atlantic. Any land beyond that limit was accorded to the Indians. There were rare trading posts and distant military outposts established in the limits of the land.
In 1768 a treaty was made at Fort Stanwix, NY, by which the Indians ceded the country known as Kentucky, as far south as the Tennessee River. This treaty was understood to remove all the reasons which supported the King's proclamation, and to give the colonists the right to occupy this land.
In 1773, Daniel Boone with his and five other families began migrating west. This was the beginning of the immigration over the wilderness road. It was, also, the beginning of bloodshed that marked the conflict in the region with the native Indians. The group was attached by Indians - six were killed, including Boone's eldest son, James.
In the year 1780, the County of Kentucky was divided into three counties by act of the Virginia Legislature. They were Jefferson, Fayette, and Lincoln. The points selected to serve as the county-seats respectively, were Louisville, which was the terminus of the Ohio River route, Lexington, toward which Boone's branch of the Wilderness Road directly led, and Harrodsburg, which was reached by the Crab Orchard branch. There was no improvement in the roads for twelve years.
Travel to the Kentucky area was achieved by either going down the Ohio River from Pittsburgh or by way of the Cumberland Gap.
Travelers from the more northerly States passed along a road which ran out from Philadelphia across Pennsylvania to Pittsburgh. This road was laid out earlier by General Forbes in his march to Pittsburgh. From Pittsburgh travelers made their way down the Ohio River.
South of this Pennsylvania road another led out from Baltimore passing through Cumberland on the Potomac River and along Braddock's road on to the Monongahela River and on to Pittsburgh and down the Ohio River. This road subsequently became the National turnpike or Cumberland road.
The roads west provided tolerable accommodations along each of these roads to Pittsburgh.
The trip from Pittsburgh by river was so tedious and dangerous that those who did not carry much baggage found the way over the Wilderness Road preferable.
The season of autumn as the most eligible for the trip, as the roads were drier, and provisions and forage more plentiful than at any other time.
As far north as Philadelphia, travelers found the most available route was through the mountains of Virginia, by way of the Cumberland Gap, and through the mountains of Eastern Kentucky. The distance from Philadelphia to the interior of Kentucky by way of the Cumberland Gap was nearly eight hundred miles.
Thus all roads from the Atlantic States converged upon two points, Pittsburgh and the Cumberland Gap.
Source: The Wilderness Road: a description of the routes of travel by which the pioneers and early settlers first came to Kentucky, The Filson Club by Thomas Speed