During his early years on the Kanawha, Boone kept a small store at Point Pleasant. Later, he moved to the neighborhood of Charleston, where he was engaged in the usual variety of occupations—piloting immigrants; as deputy surveyor of Kanawha County, surveying lands for settlers and speculators; taking small contracts for victualing the militia, who were frequently called out to protect the country from Indian forays; and in hunting. Some of his expeditions took him to the north of the Ohio, where he had several narrow escapes from capture and death at the hands of the enemy, and even into his old haunts on the Big Sandy, the Licking, and the Kentucky.
He traveled much, for a frontiersman. In 1788 he went with his wife and their son Nathan by horseback to the old Pennsylvania home in Berks County, where they spent a month with kinsfolk and friends. We find him in Maysville, on a business trip, during the year; indeed, there are evidences of numerous subsequent visits to that port. In May of the following year he was on the Monongahela River with a drove of horses for sale, Brownsville then being an important market for ginseng, horses, and cattle; and in the succeeding July he writes to a client, for whom he had done some surveying, that he would be in Philadelphia during the coming winter.
In October, 1789, there came to him, as the result of a popular petition, the appointment of lieutenant-colonel of Kanawha County—the first military organization in the valley; and in other ways he was treated with marked distinction by the primitive border folk of the valley, both because of his brilliant career in Kentucky and the fact that he was a surveyor and could write letters. One who knew him intimately at this time has left a pleasing description of the man, which will assist us in picturing him as he appeared to his new neighbors: "His large head, full chest, square shoulders, and stout form are still impressed upon my mind. He was (I think) about five feet ten inches in height, and his weight say 175. He was solid in mind as well as in body, never frivolous, thoughtless, or agitated; but was always quiet, meditative, and impressive, unpretentious, kind, and friendly in his manner. He came very much up to the idea we have of the old Grecian philosophers—particularly Diogenes."
By the summer of 1790, Indian raids again became almost unbearable. Fresh robberies and murders were daily reported in Kentucky, and along the Ohio and the Wabash. The expedition of Major J. F. Hamtramck, of the Federal Army, against the tribesmen on the Wabash, resulted in the burning of a few villages and the destruction of much corn; but Colonel Josiah Harmar's expedition in October against the towns on the Scioto and the St. Joseph, at the head of nearly 1,500 men, ended in failure and a crushing defeat, although the Indian losses were so great that the army was allowed to return to Cincinnati unmolested. Boone does not appear to have taken part in these operations, his militiamen probably being needed for home protection.
The following year the General Government for the first time took the field against the Indians in earnest. For seven years it had attempted to bring the tribesmen to terms by means of treaties, but without avail. Roused to fury by the steady increase of settlement north as well as south of the Ohio, the savages were making life a torment to the borderers. War seemed alone the remedy. In June, General Charles Scott, of Kentucky, raided the Miami and Wabash Indians. Two months later General James Wilkinson, with five hundred Kentuckians, laid waste a Miami village and captured many prisoners. These were intended but to open the road for an expedition of far greater proportions. In October, Governor Arthur St. Clair, of the Northwest Territory, a broken-down man unequal to such a task, was despatched against the Miami towns with an ill-organized army of two thousand raw troops. Upon the fourth of November they were surprised near the principal Miami village; hundreds of the men fled at the first alarm, and of those who remained over six hundred fell during the engagement, while nearly three hundred were wounded. This disastrous termination of the campaign demoralized the West and left the entire border again open to attack—an advantage which the scalping parties did not neglect.
While this disaster was occurring, Boone was again sitting in the legislature at Richmond, where he represented Kanawha County from October 17th to December 20th. The journals of the Assembly show him to have been a silent member, giving voice only in yea and nay; but he was placed upon two then important committees—religion, and propositions and licenses. It was voted to send ammunition for the militia on the Monongahela and the Kanawha, who were to be called out for the defense of the frontier. Before leaving Richmond, Boone wrote as follows to the governor:
"Monday 13th Dec 1791
"Sir as sum purson Must Carry out the armantstion [ammunition] to Red Stone [Brownsville, Pa.,] if your Exclency should have thought me a proper purson I would undertake it on conditions I have the apintment to vitel the company at Kanhowway [Kanawha] so that I Could take Down the flowre as I paste that place I am your Excelenceys most obedent omble servant
"Dal Boone."
Five days later the contract was awarded to him; and we find among his papers receipts, obtained at several places on his way home, for the lead and flints which he was to deliver to the various military centers. But the following May, Colonel George Clendennin sharply complains to the governor that the ammunition and rations which Boone was to have supplied to Captain Caperton's rangers had not yet been delivered, and that Clendennin was forced to purchase these supplies from others. It does not appear from the records how this matter was settled; but as there seems to have been no official inquiry, the non-delivery was probably the result of a misunderstanding.