Of course, as in every other settlement of inland America, the especial point to be noticed is the individual initiative of the different settlers. Neither the royal nor the provincial governments had any thing to do with the various colonies that were planted almost simultaneously on the soil of Kentucky. Each little band of pioneers had its own leaders, and was stirred by its own motives. All had heard, from different sources, of the beauty and fertility of the land, and as the great danger from the Indians was temporarily past, all alike went in to take possession, not only acting without previous agreement, but for the most part being even in ignorance of one another's designs. Yet the dangers surrounding these new-formed and far-off settlements were so numerous, and of such grave nature, that they could hardly have proved permanent had it not been for the comparatively well-organized settlement of Boon, and for the temporary immunity which Henderson's treaty purchased from the southern Indians.
The settlement of Kentucky was a much more adventurous and hazardous proceeding than had been the case with any previous westward extension of population from the old colonies; because Kentucky, instead of abutting on already settled districts, was an island in the wilderness, separated by two hundred miles of unpeopled and almost impassable forest from even the extreme outposts of the seacoast commonwealths. Hitherto every new settlement had been made by the simple process of a portion of the backwoods pioneers being thrust out in advance of the others, while, nevertheless, keeping in touch with them, and having their rear covered, as it were, by the already colonized country. Now, for the first time, a new community of pioneers sprang up, isolated in the heart of the wilderness, and thrust far beyond the uttermost limits of the old colonies, whose solid mass lay along the Atlantic seaboard. The vast belt of mountainous woodland that lay between was as complete a barrier as if it had been a broad arm of the ocean. The first American incomers to Kentucky were for several years almost cut off from the bulk of their fellows beyond the forest-clad mountains; much as, thirteen centuries before, their forebears, the first English settlers in Britain, had been cut off from the rest of the low-Dutch folk who continued to dwell on the eastern coast of the German Ocean.
Henderson and those associated with him in his scheme of land speculation began to open negotiations with the Cherokees as soon as the victory of the Great Kanawha for the moment lessened the danger to be apprehended from the northwestern Indians. In October, 1774, he and Nathaniel Hart, one of his partners in the scheme, journeyed to the Otari towns, and made their proposals. The Indians proceeded very cautiously, deputing one of their number, a chief called the Carpenter, to return with the two white envoys, and examine the goods they proposed to give in exchange. To this Henderson made no objection; on the contrary, it pleased him, for he was anxious to get an indisputable Indian title to the proposed new colony. The Indian delegate made a favorable report in January, 1775; and then the Overhill Cherokees were bidden to assemble at the Sycamore Shoals of the Watauga. The order was issued by the head-chief, Oconostota, a very old man, renowned for the prowess he had shown in former years when warring against the English. On the 17th of March, Oconostota and two other chiefs, the Raven and the Carpenter, signed the Treaty of the Sycamore Shoals, in the presence and with the assent of some twelve hundred of their tribe, half of them warriors; for all who could had come to the treaty grounds. Henderson thus obtained a grant of all the lands lying along and between the Kentucky and the Cumberland rivers. He promptly named the new colony Transylvania. The purchase money was 10,000 pounds of lawful English money; but, of course, the payment was made mainly in merchandise, and not specie. It took a number of days before the treaty was finally concluded; no rum was allowed to be sold, and there was little drunkenness, but herds of beeves were driven in, that the Indians might make a feast.
The main opposition to the treaty was made by a chief named Dragging Canoe, who continued for years to be the most inveterate foe of the white race to be found among the Cherokees. On the second day of the talk he spoke strongly against granting the Americans what they asked, pointing out, in words of glowing eloquence, how the Cherokees, who had once owned the land down to the sea, had been steadily driven back by the whites until they had reached the mountains, and warning his comrades that they must now put a stop at all hazards to further encroachments, under penalty of seeing the loss of their last hunting-grounds, by which alone their children could live. When he had finished his speech he abruptly left the ring of speakers, and the council broke up in confusion. The Indian onlookers were much impressed by what he said; and for some hours the whites were in dismay lest all further negotiations should prove fruitless. It was proposed to get the deed privately; but to this the treaty-makers would not consent, answering that they cared nothing for the treaty unless it was concluded in open council, with the full assent of all the Indians. By much exertion Dragging Canoe was finally persuaded to come back; the council was resumed next day, and finally the grant was made without further opposition. The Indians chose their own interpreter; and the treaty was read aloud and translated, sentence by sentence, before it was signed, on the fourth day of the formal talking.
The chiefs undoubtedly knew that they could transfer only a very imperfect title to the land they thus deeded away. Both Oconostota and Dragging Canoe told the white treaty-makers that the land beyond the mountains, whither they were going, was a "dark ground," a "bloody ground"; and warned them that they must go at their own risk, and not hold the Cherokees responsible, for the latter could no longer hold them by the hand. 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.355
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.356 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.357 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,358 and the McAfees.359 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. Boon was not so easily daunted; and he at once sent a special messenger to hurry forward the main body under Henderson, writing to the latter with quiet resolution and much good sense: