A Pictorial History and Trekking Guide of the Wilderness Road

By Daniel W. Weidner EdD DLitt

This book is about the history of the Wilderness Road and a trekking guide with photos. It presents the background of how Daniel Boone and a group of some thirty men blazed a trail by way of three states to connect Kingsport, Tennessee, to Middlesboro, Kentucky, and became an important roadway in modern-day industrial United States. Its beginning opened the east to the west for what was the early pioneering spirit of pioneers that settled those lands along with early tradesmen and stockmen. Its importance became famous with the discovery of iron ore in its environs of Middleboro; that is a story of unfounded lasting wealth that ended with disappointment for those of the area and Englishmen who invested heavily only to have the grade of iron ore become useless. It played its role during the Civil War and its status today in a thriving city.

It stands as a monument to Daniel Boone and the thirty men who created it, the undaunted pioneer men and women who faced and conquered natural and human hardships that made it a lasting monument to humanity as part of the history of the United States.

• Language: English
• Publisher: Page Publishing, Inc.
• Release date: Oct 4, 2022
• ISBN: 9781662485497

Book preview

Chapter 1

Introduction

Although signs along the route identify it as the Daniel Boone Wilderness Trail, I have found in my research that it is more commonly referred to as the Wilderness Road.

The Wilderness Road was the most significant route westward from 1790 to 1800, essentially blazed by Daniel Boone and a group of axmen in 1775.² So important was the road that a number of feeder trails joined it at various points: one was from Richmond, Virginia, in the north (and Harpers Ferry, West Virginia) which converged at Fort Chiswell in the Shenandoah Valley, whence it led west over the Appalachian Mountains, passed through Cumberland Gap, and on into the Bluegrass Region of Kentucky before extending to the Ohio River.

The Wilderness Road of yesteryear is an elusive fox that starts at what seems to be numerous locations, is spotted with historical markers that are, on occasion, duplicated here and there on a variety of spurs of the Southern Loop of pioneer roads and trails that collectively formed this road of Virginia, Tennessee, and Kentucky. Should a cartographic buff search topographical maps of the Appalachian range, he could see the geographic features that determined its location and importance during the migration period from 1775 to 1800.

In its earliest days, game such as buffalo (American bison), elk, and deer wandered through the region trampling out paths on their way to grazing lands. They, in turn, were pursued by various Indians that inhabited the region early and utilized these areas for their hunting grounds. Eventually the White Long Hunters, trappers, mountain men, and pioneers came to the passes for this was the road into the new lands of the unknown wilderness of the West and Southwest.

It is difficult at best to find and trace the Wilderness Road on today’s maps that are crisscrossed with red and blue lines that are seemingly a modern random artistic incongruity.

In its infancy, the road became the end of the trail for many who were dispatched by Indian raids, succumbed to diseases and accidents to become unmarked graves along the trail. But these raids did not deter others from following the trail. Enough had settled in Kentucky that by 1792, it became a state, and the road was widened to accommodate wagons.³ Though many traversed the wilderness, overcame natural and human disasters, and eventually defeated the Indians, time took its toll of the famous road.

Should someone wish to pick up its eastern segment, they would find the road starting at Wadkin’s Ferry on the Potomac River, proceeding up the Shenandoah River via the great trough in Virginia between the Blue Ridge and Allegheny ranges, then continue across the low divide where the Great Valley terminates near the headwaters of the James and Roanoke (Staunton) rivers. From this point, it fords New River at Ingles Ferry close to Radford, Virginia, before going on westward, descending the middle fork of the Holston to Long Island where the town of Kingsport, Tennessee, is now located.⁴ It is from here that Daniel Boone began to lay out the route destined to become the Wilderness Road to Middlesboro, Kentucky.⁵ Today’s road that follows this route is labeled Federal Highway No. 11, or Robert E. Lee Highway. It had, in its early days, been known as the Great Wagon Road, Irish Road, and the Pennsylvania Road. Indeed, as one travels the historic road, its signs label it the Daniel Boone Wilderness Trail.⁶

It was at Long Island on the Holston River in Kingsport, Tennessee, that Daniel Boone and his thirty axmen started out to blaze a trail to Middlesboro, Kentucky, which was destined to become the Wilderness Road. The Holston River was named for Stephen Holston, who had built a cabin some thirty feet from the headspring of the Middle Fork in about 1746.

The content of this guide is to enlighten the trekker of the historical significance of the Wilderness Road from Kingsport, Tennessee, to Middlesboro, Kentucky, during the years of 1775–1893 and to provide geographic information about its natural elements. Knowledge of distances between the historical markers is given in a table that informs the trekker where to acquire supplies. Information concerning trekking practices for the road and knowledge of trekking materials are listed.

Background information of the Wilderness Road is given as to its origin and development in an historical context. In so doing, it provides a sequential history as to who did what, when, where, and why. As such, it provides a setting for a foundation of interest in trekking the road as well as the opportunity for the trekker to realize the impact of human history on a specific region of the United States. The historic markers along the road attest to this aspect of the guide that emphasizes the significance of the road.

As a guide, it enables the individual to locate the historical markers and sites easily as well as knowing where places are to replenish supplies. The information given for each historic marker and site provides pertinent narrative history.

The unbroken path through a forested mountainous region was penetrated by animal and Indian trails, which the Long Hunters followed and turned into a wider yet primitive road, which ushered in a migration of sundry peoples and became the Wilderness Road. From its onset into the twenty-first century, it remained a most unusual piece of real estate in the development of the United States. It fathered thriving municipalities, large fields of crops, various grains, broad leaf tobacco, undulating pastures, country stores and service stations at crossroads, numerous schools, and white steeples of beckoning houses of worship.

The road is rich in natural resources for the astute adventurer to utilize. Rivers were harnessed for electric power; manufacturing plants ran at full throttle affording employment while the Bluegrass Region yielded bumper crops of lean thoroughbreds that became the envy of the elite equestrian society, who relished sipping champagne and eating strawberries at the Kentucky Derby to the strains of My Old Kentucky Home. The English aristocracy might look with envy on the Bluegrass society sporting blue blood attire on land that once was theirs.

Other than the stables, the rich coves along the road found large herds of well-fed bovine grazing on thousands of acres of lush green flora extending to distant wood-lined hills. As the road matured, its early crude earthen surface became a hardened all-weather route, where the first settlers had paused or stayed permanently to build houses, clear the lands, and raise livestock, crops, and families.

There is a different type of development in the Kentucky patches of the Wilderness Road from old Crab Orchard to Cumberland Gap, which once bore blackened evidence of the industrial revolution brought by Alexander Alan Arthur. Coal sources sprawled on hillsides close to spur lines of the Louisville and Nashville Railroad and back in hollows reached by coal trucks and wagons. The once dark and forbidding hills that were yet majestic in their wild beauty were gashed and scarred with ugly openings of coal camps with families who had quit the freedom of the forests to pursue a living digging underground.⁷

There is still the double-track rails extending parallel with Highway 25, catering to hundred-car trains loaded with black coal moving north over high trestles and passing locomotives, returning south with long trains of empty cars. The coal industry made the Cumberland Valley Division the most profitable of the entire Louisville and Nashville system. Farms along the road in Virginia still provide produce for thousands of laborers, and the bituminous coal of the nearby mountains keep the wheels of commerce turning.⁸

The Powell, Clinch, and Holston rivers drain the region crossed by the road yielding power for various industries. An alternative route of the road down the Holston to Bean’s Station and across the Cumberland Gap cuts through an important portion of the Tennessee Valley Authority area. Notable among the new industrial cities is that of Kingsport, Tennessee, at the Long Island where Byrd’s military highway of 1765 tied in with the trail made by Boone fifteen years later. It is here that the Netherlands Inn stands with historic markers telling of the beginning of the Wilderness Road where Boone and his axmen started.⁹

Countless thousands of men, women, and children trudged with their worldly possessions, drove livestock, and guided their wagons baring frozen streams, snow, rain, and dangers during their journey to the Bluegrass paradise. Soldiers, too, tramped in long lines—rugged, hungry, and suffering—rushed to victory or trod in defeat. It was a road where money-mad promoters exploited nature’s wealth, gutted the mountains, and left them orphaned.

Some, as the Daughters of the American Revolution, Daughters of the Confederacy, and the Dufield-Patt Rotary Club, took a greater interest in the old road and made efforts to provide some suitable commemoration of the old road and pass. It was proposed by the first builders of Middlesboro to erect twin equestrian statues of Gen. Grant and Gen. Lee on the Pinnacle. One would face north while the other faced south. But the lack of funding doomed the proposed project. Later came a proposal to erect a statue of Daniel Boone at the saddle of the Cumberland Gap. None of the three states involved with the road took any initiative to pay him the honor. This, too, never came to fruition.¹⁰

When considering the years of human endeavors to trek upon this serpentine route is, indeed, to take part in the history of this nation as a modern pioneer of historiography where the brave took on great challenges and won.

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² Robert Kincaid, The Wilderness Road. 2nd ed. (Middlesboro, KY: Bobbs-Merrill, 1999), 100.

³ Kincaid, 191.

⁴ Kincaid, preface.

⁵ Kincaid, 99.

⁶ Kincaid, 64.

⁷ Kincaid, 361–362.

⁸ Kincaid, 362.

⁹ Kincaid, 100.

¹⁰ Kincaid, 363.

Chapter 2

The People of the Wilderness Trail

In this chapter, background information will be provided on some of the key figures in the history of the Wilderness Road. Since they all play prominent roles in the development of the road and their settlements along it, it is important that this basic information be available to the reader as you encounter them throughout the pages of this study.

Arthur, Alexander Alan

Arthur was born on August 30, 1846, in Glasgow, Scotland, the son of Alexander and Catherine Allen, and died March 4, 1912, at age sixty-five in Middlesboro, Kentucky. Professionally, he was a businessman and engineer. In 1867, he joined the 167th Highlander Regiment and married Mary Forrest while still serving his unit. He moved several times throughout the following decade, living in Canada, Norway, and Sweden prior to emigrating to Boston in 1879. Arthur was married twice. His second wife, Nellie Goodwin, whom he married following the death of his first wife, was the one who introduced him to New England financiers.

Characterized as having been flamboyant, charismatic, and energetic, Arthur was successful in acquiring prominent American and European financial connections to fund numerous business enterprises. Many of them were said to have been overly ambitious and, therefore, failed. He played a primary role in the development of the Cumberland Gap area; wherein he was the major force in creating Middlesboro, Kentucky. With the early development of an iron and steel industry, he hoped to make Middlesboro the Pittsburgh of the South. It never came about because the iron ore became of too low quality to continue mining. Its growth was hindered further when both England and America were hit with panics in 1891 and 1893 respectively. Other than Middlesboro, he was instrumental in the development of Harrogate, Tennessee. Arthur, Tennessee, is named for him.

In Boston, he accepted a position as general manager of the Scottish-Carolina Timber and Land Company’s American operation. His endeavors were the forerunner of what became the great logging and mining operations that grew into what was to become major economic forces in the Southern Appalachians in the early twentieth century.

In the 1880s while working for the Glasgow-based Scottish-Carolina Timber and Land Company, he lived in Newport and built a large home known as The Mansion. When a torrential rain hit the company’s lands, the constructions collapsed, and Arthur was blamed for not having been able to foresee such a situation occurring.

In 1885, he traveled to Cumberland Gap to report on the feasibility of constructing a railroad in the area. Calculating the value of the iron ore deposits, he, with several investors, formed the Gap Associates in August 1886. They purchased twenty thousand acres in Bell County, Kentucky. The following year, English financiers invested in his company. It then became the American Association, Ltd. and eventually increased its property to one hundred thousand acres.

With great expectations of a Pittsburgh of the South, they named their new town Middlesboro after the steel city Middlesborough, England. Arthur proceeded to create the Knoxville, Cumberland Gap, and Louisville Railroad to have a connecting spur to Middlesboro by which to carry pig iron and coke out of the Yellow Creek Valley. The railroad was completed on August 23, 1889, and saw a number of dignitaries aboard its first ride.

Arthur and his American Associates, Ltd. company spent twenty million dollars on the Cumberland Gap venture. By 1891, the ore was too low grade for further investments. Two years later, the Panic of 1893 killed the company and Arthur’s Magic City.

Not to be dismayed, he decided to develop a suburb on the Tennessee side of the Gap, naming it Harrogate after the resort city in England and once again built a large house. The American Associates, Ltd. spent two million dollars developing the area, including the seven hundred-room Four Seasons Hotel. With the collapse of his present company in 1893, the hotel was sold and dismantled.

His dreams collapsed, and in 1897, he ventured to Alaska to engage in the Klondike Gold Rush but eventually settled in New York. He suffered a stroke and returned to Middlesboro, where he died on March 4, 1912. He is buried in the family plot in the lower, city proper, cemetery on a knoll overlooking the city facing Cumberland Gap. There is not any mention of his role in the development of Middlesboro.

Arthur, Gabriel

It is believed that Gabriel was born of English parents and became an indentured servant. He is believed to have been the first White person of record to have traveled the route of what became the Wilderness Road and find Cumberland Gap in 1674. He is labeled as a frontiersman-explorer with his career as such, beginning at age nineteen when exploring with James Needham, who was killed by their Indian guide. Arthur traveled widely with natives and possibly married an Indian woman. He ventured into the South as far as Spanish West Florida (today’s Alabama) and took part in raids in the Ohio Valley. Eventually, he reached present West Virginia to the mouth of the Kanawha River. The journey he had begun in May 1673 and terminated in June 1674 had him returning with a load of furs to Fort Henry.

Boone, Daniel

Daniel Boone was the son of Squire Boone and Sarah Morgan of the Quaker faith, who were married on July 23, 1720. Daniel was his parent’s sixth of eleven children, having been born on November 22, 1734, which is the date of our modern calendar. However, Daniel preferred that he was born on October 22 of the old-style calendar and insisted on using this date throughout his life.

He loved the forest and hunting in the Berks County area of his home in Pennsylvania.¹¹ He died on September 26, 1820, in Missouri. His formal education was little.¹² The family moved to the Yadkin Valley, North Carolina, in 1751 or 1752.

When the French and Indian War broke out (1754–1763), Daniel joined with Gen. Braddock in 1755.¹³ He married fifteen-year-old Rebecca Bryan on August 14, 1756.¹⁴ During his early life, Daniel was fortunate to meet George Washington.¹⁵

He became familiar with the Watauga and Bluegrass Regions of Kentucky while on a long hunt and became familiar with the Holston Valley in 1760.¹⁶

Daniel had served in the colonial army, and upon his discharge, he explored Kentucky for Richard Henderson.¹⁷ Boone was hired to blaze a trail through to Cumberland Gap for Henderson’s Transylvania Company. He retained thirty men to do the job and began on March 10, 1775.¹⁸ In 1777, Daniel was a captain in the Kentucky militia.¹⁹ By 1778, he was promoted to the rank of major, continuing to fight Indians in support of Kentucky settlements.²⁰ During this time, he also fought the British on the frontier.²¹ Boone led a force at Bryan’s Station during the American Revolution.²² He and his Kentuckians moved on to Blue Licks.²³ He was now Lt. Col. Daniel Boone.²⁴ Engaging Indians in a forced-march battle, Boone and his men were in trouble as many scattered.²⁵ In the foray, his son, Israel, was killed. Later he was to lose another son, James, to the Indians. Daniel had urged Israel to stay at home, but he refused, wanting to be with his father. When the skirmish got bad, he said to his father, Father, I won’t leave you.²⁶ Blue Licks was a disaster for the colonials.²⁷

In August 1787, Daniel was free to attend the October meeting of the state legislature of Kentucky, wherein he became occupied for the remainder of the year until its adjournment on January 8, 1788.²⁸

In 1791, Daniel was another member of the Assembly for Kanawha County, where he served on the committee on religion and another on preparations and licenses.²⁹

As late as March 4, 1792, he was still in the service of Kentucky delivering supplies to settlements along the Ohio and elsewhere. But his service did not go without complaint from another, and he was brought before a judge to explain allegations of which he was cleared, yet the money owed him would never be seen.³⁰ When it came to lands to be received by certificate for which he had fought and cleared, he did not receive any.³¹

Eventually after a great deal of bickering and the law, he grew weary of perpetual recriminations and was determined never to defend another land suit. On his deathbed, he advised his children to never contest any land claims that might remain in his estate.³²

During his lifetime, he was a shopkeeper having had a store in Maysville, Missouri.³³

This he mentioned when he returned to Kentucky in 1817 for an honorary dinner held for him. He told John M. Peck, Now I am ready and willing to die. I am relieved from a burden that has long oppressed me. I have paid all my debts, and no one will say when I am gone, Boone was a dishonest man. I am perfectly willing to die.³⁴

Feeling his age, he mounted his horse, Roan, and took a ride. He took ill and lied in bed three days with acute indigestion, probably helped along by his adoring grandchildren who plied him with too many sweet potatoes and other delicacies. After a short illness without pain, the great frontiersman passed away. The Missouri Legislature adjourned upon hearing of his death. Rebecca had already died. The old warrior was laid to rest in the coffin he cherished. His initial grave was beside Rebecca on the little knoll looking down to the river through the trees resting in peace.³⁵

After twenty years, Kentuckians wanted their hero back. Missouri consented. The bodies of Daniel and Rebecca were moved by a highly official delegation. His bones were rearranged in a new coffin, and a cast was made of his skull. Four white horses drew the hearse. Pioneers from all parts of the state were pallbearers. The Hon. John J. Crittenden, a senator and attorney general, spoke. There was a brilliant military procession. The Kentucky militia buried its lieutenant colonel in style. Kentucky rifles fired off a salute. The Spanish had received him formally in St.