The Wilderness Road was a path westward to Kentucky established by Daniel Boone and followed by thousands of settlers in the late 1700s and early 1800s. At its beginning, in the early 1770s, it was a road in name only.

Boone and the frontiersmen he supervised managed to link together a route comprising old Indian pathways and trails used for centuries by herds of buffalo. Over time it was improved and widened to accommodate the wagons of travelers.


The Wilderness Road passed through the Cumberland Gap, a natural opening in the Appalachian mountain range, and became one of the main routes westward. It was in operation decades before other routes to the frontier such as the National Road and the Erie Canal.

Though Daniel Boone's name has always been associated with the Wilderness Road, he was actually acting in the employ of a land speculator, Judge Richard Henderson. Recognizing the value of vast tracts of land in Kentucky, Henderson had formed the Transylvania Company. The purpose of the business enterprise was to settle thousands of "emigrants" from the East Coast to the fertile farmlands of Kentucky.

Henderson faced several obstacles, including the aggressive hostility of the Indians who were becoming increasingly suspicious of white encroachment on traditional hunting lands.

And a nagging problem was the shaky legal foundation of the entire endeavor. Legal problems with land ownership thwarted even Daniel Boone, who became embittered and left Kentucky by the end of the 1700s.

But his work on the Wilderness Road in the 1770s stands as a remarkable achievement which made westward expansion of the United States possible.

Blazing the Trail

Though Daniel Boone is often credited as having discovered the Cumberland Gap, he had actually heard about it from others. But Boone, in his explorations in the 1760s, was able to establish its location so others could find it.

At some point in the early 1770s Boone met Richard Henderson, who had recently retired as a judge of a colonial court in North Carolina. Henderson had a plan to buy up land on the other side of the Appalachian mountains from the Cherokees.

The purchase of land in that matter by individuals was not considered legal. And, the Cherokees had no legal right to sell the land to Henderson anyway. But Henderson believed that if he could get settlers into the territory, which he would call Transylvania, it could develop its own colonial government.

Henderson's plans did not work out as he hoped. But one part of his grand scheme, to have Daniel Boone mark a trail westward, did become a historic accomplishment.

In the spring of 1775 Daniel Boone, along with 30 armed men he had hired, set to work establishing the trail westward. By linking up old Indian trails and paths which had created over many decades by herds of buffalo, they made a rough road settlers could follow.