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.