Dragging Canoe especially told Henderson that there was a black cloud hanging over the land, for it lay in the path of the northwestern Indians--who were already at war with the Cherokees, and would surely show as little mercy to the white men as to the red.
Another old chief said to Boon: "Brother, we have given you a fine land, but I believe you will have much trouble in settling it." What he said was true, and the whites were taught by years of long warfare that Kentucky was indeed what the Cherokees called it, a dark and bloody ground.[2] After Henderson's main treaty was concluded, the Watauga Association entered into another, by which they secured from the Cherokees, for 2,000 pounds sterling, the lands they had already leased.
As soon as it became evident that the Indians would consent to the treaty, Henderson sent Boon ahead with a company of thirty men to clear a trail from the Holston to the Kentucky.[3] This, the first regular path opened into the wilderness, was long called Boon's trace, and became forever famous in Kentucky history as the Wilderness Road, the track along which so many tens of thousands travelled while journeying to their hoped-for homes in the bountiful west.

Boon started on March 10th with his sturdy band of rifle-bearing axemen, and chopped out a narrow bridle-path--a pony trail, as it would now be called in the west.
It led over Cumberland Gap, and crossed Cumberland, Laurel, and Rockcastle rivers at fords that were swimming deep in the time of freshets.

Where it went through tall, open timber, it was marked by blazes on the tree trunks, while a regular path was cut and trodden out through the thickets of underbrush and the dense canebrakes and reed-beds.
After a fortnight's hard work the party had almost reached the banks of the Kentucky River, and deemed that their chief trials were over.

But half an hour before daybreak on the morning of the 25th, as they lay round their smouldering camp-fires, they were attacked by some Indians, who killed two of them and wounded a third; the others sprang to arms at once, and stood their ground without suffering further loss or damage till it grew light, when the Indians silently drew off.[4] Continuing his course, Boon reached the Kentucky River, and on April 1st began to build Boonsborough, on an open plain where there was a lick with two sulphur springs.
Meanwhile other pioneers, as hardy and enterprising as Boon's companions, had likewise made up their minds that they would come in to possess the land; and in bands or small parties they had crossed the mountains or floated down the Ohio, under the leadership of such men as Harrod, Logan,[5] and the McAfees.[6] But hardly had they built their slight log-cabins, covered with brush or bark, and broken ground for the corn-planting, when some small Indian war-parties, including that which had attacked Boon's company, appeared among them.

Several men were "killed and sculped," as Boon phrased it; and the panic among the rest was very great, insomuch that many forthwith set out to return.