The governor replied brusquely that it was wholly unnecessary for him to take the time to give an examination, as no one could in that length of time and with such books become proficient.

“Sir,” replied Richard Henderson not a whit dismayed, “I am an applicant for examination; it is your duty to examine me and if found worthy, to grant me a license; if otherwise, to refuse one.”

It can well be imagined how quickly the governor bristled up and how mercilessly he would “quiz” a lad who informed him in such a spirited manner what the duties of his office required of him. But the running fire of questions did not daunt the candidate more than had the governor’s indifference—and the young Richard received at the close of the interview, not only a license, but what meant more, many encomiums from his governor.

Henderson soon acquired a good practice and became a judge on the bench of the Superior Court. In 1774 the conflict with the British agent in North Carolina was precipitated, and the colonial government was abolished. It was at this time that Judge Henderson became interested in the desire of the Cherokee Indians to sell land. Henderson’s plan was to purchase from the Cherokees the great territory lying south of the Kentucky River—one-half the present state of Kentucky. This was quite against the laws and traditions of the only colony which had any valid claim to the territory—Virginia, his native state—but this seemed to matter not to Henderson and his associates; these were John Williams, under whom Henderson had studied law, Leonard Henley Bullock, James Hogg, Nathaniel Thomas, David Hart, John Luttrell, and William Johnstone. At the very beginning of the century Virginia had passed an act forbidding the private purchase of lands from the Indians. The founders of Transylvania evidently doubted Virginia’s sweeping claims to the entire interior of the continent—at any rate land companies seemed to be the only means by which the vast wildernesses beyond the mountains could be opened up and settled. Though Virginia soon proved the invalidity of the purchase, she at the same time was frank enough to admit that Henderson’s Company had done a good work in giving an impetus to westward expansion, by appropriately recompensing the North Carolinians for their expenditure and labors.

Henderson’s purchase was gigantic in its proportions, embracing nearly twenty million acres. The consideration was ten thousand pounds sterling. The purchase was made at the advance settlement at Watauga, March 17, 1775—only a month before the outbreak at Lexington and Concord. Henderson employed Boone to assist in the transaction, and immediately after engaged him to mark out the road through Cumberland Gap to a settlement in Kentucky, where the Transylvania Company (as Henderson strangely named his organization) was to begin the occupation of the empire it had nominally secured. Of this Boone writes modestly that he was “solicited by a number of North Carolina gentlemen, that were about purchasing the lands lying on the south side of the Kentucky River, from the Cherokee Indians, to attend their treaty at Watauga, in March, 1775, to negotiate with them, and mention the boundaries of the purchase. This I accepted, and at the request of the same gentlemen undertook to mark out a road in the best passage from the settlement through the wilderness to Kentucky, with such assistance as I thought necessary to employ for such an important undertaking.”

As in the case of Nemacolin’s Path across the Alleghenies, so now a second westward Indian pathway was blazed for white man’s use; and if the Transylvania Colony can in no other respect be said to have been successful, it certainly conferred an inestimable good upon Virginia and North Carolina and the nation, when it marked out through the hand of Boone the Wilderness Road to Kentucky. From Watauga the path led up to the Gap, where it joined the great Warrior’s Path which came down through Kentucky from the Scioto Valley in Ohio. For about fifty miles Boone’s Road followed this path northward, whereupon, leaving the Indian trail, Boone bore to the west, marking his course on a buffalo trace toward “Hazel Patch” to the Rockcastle. The buffalo path was followed onward up Roundstone Creek, through “Boone’s Gap” in Big Hill; through the present county of Madison, Kentucky; and down little Otter Creek to the Kentucky River. Here Boonesborough was built for the Transylvania Colony, which became the temporary center of Kentucky.

Felix Walker, one of Boone’s road-making party, made an autobiographical statement about 1824 of this brave attempt to cut a white man’s path into Kentucky. From this statement these quotations from De Bow’s Review (1854) are pertinent:

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