From: Semple, 1903:67 et seq
But after the Revolution and Wayne's defeat of the northern savages in 1794, and especially after the opening up of the Northwest, the Ohio route was much used, except for the return trip to the East. The current that bore the outbound settler down the tide of the western waters was his obstacle when he turned his face towards the coast. Hence this difficulty and the horror of Indian attack deflected much of the westward movement to the land route from southwestern Virginia by Cumberland Gap. The intervening trail from the head streams of the James River to the Greenbrier tributary of the Kanawha,and the rugged portal opened to the same river and to the Tug Fork of the Big Sandy by the deep canon of the New, seem to have been little used by the pioneers. Buffalo trace and Indian war-path had pointed out the easiest way across the mountain barrier, and these the backwoodsman followed. The Big Sandy and New River route was the common war-path of the Shawnees when making incursions from Ohio into the territory of their relentless foes, the Catawbas of North Carolina, because it was the most direct line from the villages along the Scioto ; but the light equipment of savage warriors permitted rougher traveling than the pack-horses and cattle herds of the outbound settler. The Cumberland Gap route was the natural avenue to the West for emigrants from Virginia and the Carolinas, but it was preferred also by colonists from Philadelphia when they carried little baggage, though the distance from that city to the interior of Kentucky was eight hundred miles. From Philadelphia an established line of travel led across the Potomac by Wadkin's Ferry, and up the Valley of Virginia along the old war-trail of the Iroquois and Cherokee, over the low watershed to the New River. The pioneer crossed that stream and continued up its western affluent, Reed Creek, which on an almost level divide interlocks with the head streams of the Holston. Here the western trail was joined by another path from Richmond, Virginia, and here at the " forks of the road " was Fort Chissel, the block-house built in 1758 to hold the Cherokees in check. At this point began the Wilderness Road. The distance to Cumberland Gap was two hundred miles.
From the upper Holston, the Wilderness Road turned • west, and by a maze of gaps and their approaching streams which furrowed the mountain sides, it crossed the parallel ranges of Clinch, Powell, and Walden mountains to the Powell River, and turned down this valley to Cumberland Gap, an old "wind-gap" which opened an easy gateway (1600 feet elevation) through Cumberland Mountain to the West. Just beyond the pass the frontiersman struck the " Warriors Path," an Indian trail which ran between the Shawnee villages at the mouth of the Scioto in Ohio and the Cherokee lands in eastern Tennessee. The Wilderness Road, as tracked in 1775 by Daniel Boone for Colonel Henderson, followed this Indian trail across the ford of the Cumberland, where this river breaks through Pine Mountain, and down the stream for a few miles to Flat Lick; but here it turned northwest, and followed a buffalo trace along the ridges over to Rockcastle River. In Kentucky the pioneer, following the example of the buffalo, avoided the immediate watercourses ; for in contrast to the broad basins of the Allegheny rivers, these streams had carved out the surface of the Cumberland Plateau into deep V-shaped valleys, which afforded only precarious foothold for the traveler and necessitated continuous crossing of their rushing currents.
By buffalo trace the road continued north from the Rockcastle River through Boone's Gap in the rugged barrier of the Big Hill range (present route of the Louisville and Nashville Railroad) to Otter Creek and the Kentucky River at Fort Boonesborough, thence to Lexington and the smiling lands of the Bluegrass. From Rockcastle River another branch of the Wilderness Road, blazed by Logan in 1775, turned northwest and, by a natural gateway near Crab Orchard, reached level land near the present town of Stanford, where Logan built Station St. Asaphs. This track became more important than Boone's trail to the north because it led more directly to the attractive level lands of Kentucky, and, passing through Danville, Bardstown, and Bullitt's Lick, terminated at the Falls of the Ohio, whence was the readiest connection with the old French trading-posts on the Mississippi and the Wabash. The route taken by Robertson to the Tennessee country followed the Wilderness Road beyond Cumberland Gap, and then turned southwest, guided largely by buffalo traces seeking pools and salt-licks, to the " bend of the Cumberland" where Nashville grew up; but the women, children, and baggage for the new settlement made a long and dangerous journey in flatboats, dugouts, and canoes down the winding course of the Tennessee River to the Ohio, and up the Cumberland to the little stockade on the bluffs. But later (1783) a new road from the confluence of the Holston and the Clinch rivers passed by easy ascent over Cumberland Mountain to the valley of the Cumberland and Nashville. This route was joined by a trail also from North Carolina, and at the mouth of the French Broad River by still another from South Carolina. Thus several roads from the east converged upon the upper Tennessee, just as Cumberland Gap was a plexus of other routes aiming at Kentucky and the West.
At first only blazed trails through the great wilderness, then traces trodden out more plainly by the feet of pioneers and pack-horses, impassable to wagons, these transmontane roads offered no easy conditions for travel. The floor of the Great Valley in southern Virginia rises to 1700 feet and the linear ranges to be crossed were in general only 6OO or 800 feet higher; but each in turn barred the western horizon like a wall, and only here and there were their even sky-lines notched by a gap. These gaps were never opposite one another in the successive ranges, so the traveler had to take a circuitous way up and down the intervening valleys from pass to pass. He had to ford trough streams and mountain creeks, which one summer rain might raise to rushing torrents. For food he depended upon game or the cattle which he drove along with him, while an outlying habitation occasionally supplied him with bacon and corn-meal. The danger of attack from the Cherokees, stirred to hostility first by the French and later by the Spanish, was always there, but never so imminent as the perils on the Ohio from the Shawnees. But in spite of dangers and hardships, the trail through the wilderness had its joys, — the charm of the wondrous Appalachian forests, the flicker of sunlight through the high-reaching trees, the plunge into a tunnel of green through the tender spring underbrush, the sense of strong, pulsing life with the upward climb, finally the deep-drawn breath on the summit before the outstretched billows of land, and the hope of opportunity beyond. The distribution of trans-Allegheny population in 1790 was in close relation with the western highways. Pennsylvania settlements formed a continuous line from the Juniata to the Allegheny, Monongahela, and Ohio almost to the mouth of the Muskingum River. In Virginia there was an unbroken area of settlement to the western rim of the Great Appalachian Valley; but beyond the Greenbrier and the New, the frontiersman had passed by the rugged country of the Cumberland Plateau along the upper Kanawha to make a small settlement at its mouth. The frontier farms and villages of southwestern Virginia merged into "the independent state of Franklin " in the parallel valleys of the Holston and the Clinch. Downstream moved the tide of settlement. Where the Holston and French Broad unite to form the Tennessee, White and Conner in 1787 located a warrant of land which they had received as pay for military service in the Revolution, and about their fort the town of Knoxville was laid out soon afterwards. In 1785 a settlement was attempted at the Muscle Shoals of the Tennessee River in northern Alabama, and a few years later Sevier and others secured a grant of land for settlement just south of the Shoals. The attraction here was a geographical one. The obstruction to navigation by the rapids necessitated a carry at this point, which therefore became a halting-place for travelers. Furthermore, the Big Bear River, a southern tributary of the Tennessee, connected by a short portage with the head streams of the Tombigbee and Yazoo, thus opening up lines of trade with the lower Mississippi and Mobile Bay.
To the west Nashville, whose eighty or ninety cabins were a center for the five thousand pioneers settled for eighty miles along the river, was a product partly of the waterway formed by the Tennessee and the Cumberland, and partly of the land routes through the gaps in the Cumberland range. In the same manner the Kentucky settlements were born of the Ohio and the Wilderness Road. The Cumberland and Kentucky settlements were separated from the frontier of civilization in Virginia by a wide zone of wilderness, the rugged upland of the Cumberland Plateau, a region condemned even to-day by its geographical conditions to isolation, poverty, and a retarded civilization.