The earliest known path through Southwest Virginia was an ancient buffalo and Indian trace. When and who the first white man to travel over this trace we have no way of ascertaining at this late date.

That hunters had been on this trace much earlier than most historians think can be proven by the Journal of Dr. Thomas Walker when he was commissioned by the Loyal Land Company in 1750 to make an exploration of lands which they had been granted. On April 9, 1750, Dr. Walker makes this entry in his Journal:
     "We traveled to a river, which I supposed to be that which the hunters call Clinche's River, from Clinch, a hunter who first found it."
     
This entry shows beyond doubt that the trace and river were known to hunters prior to 1750. Later in the 1760's when long hunts became more profitable and more frequent this ancient trace became known, far and wide, as the Hunters Trace, and the very word "Hunters" still clings as an identifying name for
certain places such as Hunter's Valley in Scott County, Virginia.
     
This trace, as all roads do, had several converging paths leading into it. The first long hunts were organized along the New River and later on Holston River, near Chilhowie. From these points three paths were well known. One lead from the Holston by way of Saltville down through Elk Garden to Castlewood.
The second from Abingdon through Little Moccasin Gap to Castlewood. The third ran from Abingdon via Bristol and down Reedy Creek and veered northwest before reaching Long Island (Kingsport) across Pine Mountain through Moccasin Gap, linking up with the main Hunters Trace at Little Lick (Duffield), where it passed over Kane's Gap onto Wallens Creek and down the Powell Valley to Cumberland Gap. This latter path later became the main branch of the Great Wilderness Road.
     
The first two paths which converged at Castlewood to form a single trace from that place through Powell Valley to Cumberland Gap ran down the brow of a low hill on the south side of Clinch River at Dungannon, north of the present bridge and was shown on the first map of the area made by Daniel Smith
in 1774 as "Hunter's Ford." The crossing later became known as "Osborne's Ford" after Stephen Osborne settled at the site. From Hunter's Ford the path led down a valley on the north side of Clinch River between Nuckner's Ridge and Stone Mountain, and known to this day in Scott County as Hunter's Valley. It crossed Big Stony Creek at a place once known as Ka, Virginia, then out Hunter's Valley through Rye Cove to Sunbright, and across Kane's Gap onto Wallen's Creek. At Little Flat Lick all three traces became one before entering Kane's Gap and thence down Powell Valley to Cumberland Gap.
     
Daniel Boone was familiar, no doubt, with all three traces. Boone's first trip into Southwest Virginia, was probably about 1767 when he camped at Abingdon and named it Wolf Hills. He came into the Valley of the Holston a number of times in 1767 and 1768.
     
Daniel Bryan, Boone's nephew and namesake, in 1843, wrote to Dr. Lyman C. Draper, the following account of Boone's trip through this section into Holston Valley and on into Kentucky. This trip is certainly that made by Boone in 1769, for it was John Finley, a noted long hunter whose acquaintance Boone had made in Braddock's Army and who first told Boone of Kentucky, who led him through
Cumberland Gap in 1769, Boone having missed the Gap on two previous searches. Bryan's description of the route follows:
     "Boone agreed to go and took John Stewart, as his companion, John Finley, James Holden, James Mooney and William Conley, six in all."
     "On the first day of May, 1769, started from Boone's on the Head of Yadkin they took their course westwardly crossing the Blue or Big Mountain to the three forks of the New River lower down called Kenaway, thence over Stone Mountain to a place called the Stares (Stairs), thence over the Iron Mountain into Holston Valley, then across the valley to Moccasin Gap in the Clinch Mountain. I, Daniel Bryan have traveled the same route. They then continued their route or course westwardly crossing Waldens Ridge and Powell Mountain into Powells Valley, then down the Valley leaving Cumberland Mount but a little to their right, so on to Cumberland Gap." (Draper Mss)
     
Daniel Bryan, here traces Boone's first trip over the entire distance of the Wilderness Road.
     
In 1773, Boone, accompanied by Benjamin Cutberth went to Kentucky to hunt and no doubt, to locate a place for his intended settlement. It was on the return from this trip that Boone met with Captains  William Russell and David Gass at Castlewood, and induced them to join him in an attempted settlement in
Kentucky.
     
Returning to the Yadkin Valley, Boone sold his farm and on September 25, 1773, started with his party of settlers to Kentucky. The Bryan party, Boone's relatives, were to rendevous with him in Powell Valley and make the most dangerous part of the journey together.
     
Somewhere in the vicinity of Abingdon, Boone sent his son, James, with John and Richard Mendenhall, across country to inform Russell and Gass that the party was on their way and to get flour, tools, and cattle for the settlement. Either at Castlewood, or along the way, the little party was joined by Isaac Crabtree and a boy by the name of Drake, son of Joseph Drake who was killed by Indians at
Boonesboro in 1778. Both of these young men lived with their parents on the road leading from the Holston to the Salt Works, (now Saltville). It is the belief of this writer that this party traveled from Abingdon to Castlewood, through Little Moccasin Gap, much as the road runs today.
     
Leaving Captain William Russell's place at Castlewood, along with his son, Henry Russell and two Negro servants belonging to Russell, the party started forward on a section of the old Hunters Path previously described. They were to join Boone's main party in Powell Valley. They traveled down the south side of Clinch River, crossing Hunter's Ford, through Hunters Valley and across Powell Mountain at Kane's Gap, onto the head of Wallen Creek, when darkness came upon them and they went into camp at the old ford of Wallen's Creek on October 9, 1773. At daybreak on the next day, as everyone knows, the small party was set upon and masscreed by the Indians, with the exception of Isaac Crabtree and one of the Negro slaves.
     
Logical reasoning tells us that Boone did not travel to Castlewood with his main party, or else he would have sent his son to inform Russell and Gass of his movements. It is the belief of this writer that Boone and his main party used the third artery described as one of the converging paths of the old Hunters Trace, and this is also the consensus of the late R. M. Addington, in his History of Scott County, Virginia, Addington details this route through Scott County, and I quote herewith:
     "It is not possible with the data at hand, to trace with absolute certainty, the location of the Kentucky Path at every point throughout its length. Like other roads, both then and now, it was subject to such alterations as suited the fancy of convenience of those who traveled over it, and divergence was, of course, always possible between the 'gaps'. Moccasin Gap, was no doubt, reached from the Holston settlements by more than one way. In general, however, the following description of the Kentucky Path may be taken as fairly accurate in so far as its passage through Scott County is concerned. It passed from Shelby's Fort (now Bristol) down Reedy Creek to the Blockhouse. Boone's original place of rendevous, however, did not usually take him as far west as the site of Kingsport. He traveled down Reedy Creek to the neighborhood of Peltier, and then turned north to the Virginia-Tennessee boundary line, thence by the
way of the Blockhouse to the ford just above Holston Bridge. From this ford he took a northwest course, passing over Little Pine Mountain at a point where its elevation has been greatly reduced by Big Moccasin Creek. He then passed through Big Moccasin Gap, the great eastern gateway of the Kentucky Path. Thence up Little Moccasin Valley in the low divide which separates Little Moccasin from Troublesome Creek. At or near the Old Virginia and Southern depot at Speers Ferry, the path turned aside from the narrow valley of Troublesome Creek, and passed along the south side of a limestone hill to the north of the late J. M. Horton residence, until it reached a narrow ravine at Horton's Chapel. Here it dropped down the ravine to the ford at Speer's Ferry. Persons yet alive remember and point out the depression of the old Trace where it passed along the side of the limestone ridge from the old Virginia and Southern depot to Horton's Chapel. (See deeds Michael Darter, George Graham and George George.)
     "After crossing Clinch River at Speers Ferry, the path passed up the west bank of the same to the Ford of Stock Creek." (Present site of Clinchport). From Clinchport it followed the meanders of Big Stock creek up almost to the Natural Tunnel. Here it turned to the left around Tunnel Hill by way of Horton's
Summit, to the Little Flat Lick (now Duffield), near the new schoolhouse at Duffield. It may be stated in this connection that foot travelers and pack horse trains often passed up the Devil's Race Path Branch to the top of Purchase Ridge, and then descended into the valley of the North Fork of Clinch, near the Little
Flat Lick. Little Flat Lick it seems was one of the best known places on the Kentucky Path. Not one of the early travelers over the Path, who has left an account of his itinerary, has failed to mention Little Flat Lick.
     "From Little Flat Lick, there seems to have been, at least, two ways of reached Powells Valley. One of these, and this was probably the oldest, passed over Powells Mountain at or near Kane's Gap, and descended into Powells Valley not far from the head of Wallen's Creek, where Scott's Fort was located.
The other, and this was no doubt, the route taken by wagons, passed from Little Flat Lick down the valley to the North Fork of Clinch, by way of Pattonsville, over Powell Mountain to Stickleyville very much as the present wagon road runs."

After the massacre of Boone and Russell's sons it was a well established fact that Daniel boone brought his family and his brother, Squire Boone, back to Castlewood and lived in a cabin on the farm of Captain David Gass. In 1774 he was in command of troops at Moore's and Blackmore's Forts on the Clinch. The court of Washington County, Virginia, invested him with the rank of Lieutenant and then Captain of Militia, the only military rank he ever held.

It was from Castlewood in 1774 that Daniel Boone and Michael Stoner were sent to warn land surveyors in Kentucky of a possible war by the Shawnee Indians. This time, from best evidence available, they traveled through Pound Gap in Wise County, which Boone called "Sounding Gap," to the falls of the Ohio and back through Cumberland Gap to Castlewood.

In the early spring of 1775, Daniel Boone and a party of about thirty men blazed a trail from the Holston into Kentucky. This road was no doubt the one described by Addington, and it was only a trail, suitable for pack horses and foot travelers, and not for wagons, except from the Holston to Martin's Station in Lee County (site of Jonesville). It was over this route that Boone set out from Castlewood in the spring of 1775 to found the permanent settlement of Boonesboro.

Historical Sketches of Southwest Virginia, Published by the Historical Society of Southwest Virginia, publication 12 - 1978, pages 1 to 4.