Leaving Fort Watauga March 20, the party, chief of which were Henderson, Hart, and Luttrell, reached Captain Joseph Martin's station in Powell's Valley on the thirtieth. Of the experiences of these men, recounted so interestingly in Henderson's little yellow diary, nothing is so significant as the parties of pioneers which they soon began to meet retreating from Kentucky. The first of these hurrying bands of fugitives was encountered as early as April 7, and between that date and April 19 at least seventy-six fugitives from the "dark and bloody ground" met and passed Henderson's little colony of forty. Lewis's victory of the Summer before had embittered the savages beyond all words; and now, as the Spring of 1775 dawned in the lonely mountain valleys, these first adventurers into Kentucky were hurrying eastward. And this dread of Indian hostility was not a chimera; even as Boone's party was hacking its route to the Kentucky River, it was ambushed in camp by an Indian horde, which assailed it when night was darkest, just before dawn; one man was killed and two were wounded, one of them fatally.
Now it was that Boone sent Henderson those thrilling words which can be understood only when we realize that the Indian marauders were driving out of Kentucky the entire van which came there and began settling in 1774. "My advice to you, Sir," wrote Boone from that bloody battleground on the trail, "is to come or send as soon as possible. Your company is desired greatly, for the people are very uneasy, but are willing to stay and venture their lives with you, and now is the time to frustrate the intentions of the Indians, and keep the country whilst we are in it. If we give way to them now, it will ever be the case."
There is, unfortunately, no portrait of Richard Henderson in existence; if one picture by some magic art could be secured, those who are proudest of his memory could surely prefer no scene to this: a man a little above average height, broad of shoulders but not fleshy, clad in the rough garb of the typical pioneer, standing in Boone's trail on a ragged spur of the gray-grained Cumberlands, pleading with a pale-faced, disheartened Kentucky pioneer, to turn about, join his company, and return to the Kentucky River. For this was the mission of his life—to give heart to that precious movement into Kentucky at this critical first hour of her history. A beginning had been made, but it was on the point of being swept from its feet. The Transylvania Company, led with courage and confidence by Boone and Henderson, ignored the fears of fugitives and triumphed splendidly in the face of every known and many unknown fears.
At noon of Saturday, April 8, Henderson and his followers were toiling up the ascent into Cumberland Gap. On this day a returning party as large as Henderson's was encountered. "Met about 40 persons returning from the Cantuckey," wrote Henderson in his diary. "On Acct. of the Late Murder by the Indians, could prevail one [on] one only to return. Memo. Several Virginians who were with us returned." On the twelfth another company of fugitives was met on Richmond Creek; William Calk, one of Henderson's party, jotted this down in his journal: "There we met another Company going back [to Virginia]; they tell such News Abram and Drake is afraid to go aney further." This "Abram " was Abraham Hanks, uncle of Nancy Hanks, the mother of Abraham Lincoln. But pushing bravely on, Henderson and his daring associates reached the site of the new Boonesborough (Fort Boone, Henderson called it) on the twentieth of April.
From this it is well to date the founding of a genuine settlement in Kentucky, one day after the rattle of that running fire of muskets at Lexington and Concord which rang around the world. In an indefinite sense, there were settlements in Kentucky before this; but no promoter-friend of Kentucky ever coaxed back over the Cumberland Mountains any of the founders of Boonesborough! True, Boonesborough itself did not exist permanently; but not because the land was deserted. Boonesborough was not on the direct line from Cumberland Gap to the "Falls of the Ohio" (Louisville), and did not play the part in later Kentucky history that Harrodsburg and Crab Orchard did. It was, however, the first important fortified Kentucky station, and its builders, chief of whom was Richard Henderson, received their heroic inspiration from no persons or parties in existence in Kentucky when they came thither. Henderson's determination to hold the ground gained is seen in the following letter written in July, 1775, to Captain Martin, in Powell's Valley, who had just given the Indians a bloody check: "... Your spirited conduct gives me great pleasure. Keep your men in heart if possible; now is your time, the Indians must not drive us." A touch of the loneliness of Judge Henderson's situation is sensed in another letter to Martin: "I long much to hear from you," he writes from the banks of the far-away Kentucky, "pray write me at large, how the matter goes with you in the valley, as well as what passes in Virginia."
Little wonder he was anxious concerning Virginia's attitude toward his purchase and the bold advance of his party of colonizers, from which several Virginians had deserted. There could be no doubt of Virginia's opinion of these North Carolinians who had taught that colony what could be done in the West by brave, determined men. Henderson's purchase was annulled, and Henderson and his compatriots were described as vagabond interlopers, in a governor's anathema. Before this was known, Henderson issued a regular call for a meeting of the colonists to take the initial steps of forming a State government. But all that Henderson planned is not to our purpose here. A rush of Virginians through the doorway in Cumberland Gap, which Boone and Henderson had opened, swept the inchoate state of Transylvania from record and almost from memory. The Transylvania Company never survived the Virginia governor's proclamation, North Carolina joining Virginia in repudiating the private purchase. Actual settlers on Henderson's purchase, however, were permitted to remain in title; and, in return for the money expended by Henderson and his associates, Virginia granted his company two hundred thousand acres of land in the vicinity of Henderson, Kentucky; and North Carolina granted an equal amount in Carter's Valley near the Cumberland Mountains. In each case the actual acreage was about double that mentioned in the grant.
But this appropriation of nearly a million acres to the Henderson Company cannot be viewed at this day as other than a payment for great value received. From any standpoint Richard Henderson's brave advance into Kentucky, in April, 1775, must be considered one of the most heroic displays of that typical American spirit of comprehensive aggrandizement of which so much is heard to-day. Its great value may be guessed from the moral effect of the founding of Fort Boone at the critical hour when the Revolutionary flames, so long burning in secret, burst forth to enlighten the world. It meant much to the East that Henderson and Boone should prove that a settlement on the lower Ohio Basin could be made and maintained; it meant everything to the infant West that Kentucky should so soon begin to fill with men, women, and children. The debt of Ohio, Indiana, and Illinois to Kentucky can never be paid and probably never will be appropriately recognized. The lands north of the Ohio were freed from savage dominion largely by the raiding Kentuckians. It is certain that the most spectacular campaign in Western history, Clark's conquest of Illinois, would never have taken place in 1778 if Henderson and Boone had not placed the possibility of successful Kentucky immigration beyond a reasonable doubt in 1775.
Judge Henderson returned to North Carolina upon the failure of the Transylvania Company, no doubt depressed and disappointed. The later allotment of land to the Transylvania Company by Virginia and North Carolina in part annulled the severe early defamatory charges of the Virginia governor. He lived to a peaceful old age, and lies buried near his old colonial mansion near Williamstown, North Carolina.