It is said that no road is of greater historical significance to the settling of “Kaintuck” and the opening of America’s West than our Commonwealth’s Wilderness Road. More than half the central Kentucky population can trace family trees back to the hundreds of thousands of Irish-Scottish-German-English immigrants who departed the East Coast from 1775-1810—often from the port of Philadelphia or Baltimore—traveled hundreds of miles along the Allegheny Mountain range, walked through the Cumberland Gap south of Middlesboro, and made their way over the Wilderness Road to their new homes in Kentucky.
Destitute and land hungry, the majority of these immigrants wanted more than anything to move straight to the backcountry, where they would seize, in the words of a Colonial official, “any sort of vacant land they could find.” Some had a little money left from their passage to America and could have rented land in settled areas closer to the East Coast but chose not to. As one immigrant explained: “We having been, before we came here, so much oppressed and harassed by landlords in our own country, from which we with great losses, dangers, and difficulties came to this foreign world to be freed from such oppression.”
Their remarkable journeys turned people of various nationalities into Americans … and Kentuckians.
Traveling by foot and horseback, usually in single file over rocky dirt paths created over hundreds of years by woodland buffalo, deer and elk, and later by Cherokee and Shawnee, these pioneers settled the Great Meadow—now known as the Bluegrass region, central Kentucky. The route was dangerous and exhausting as it wound its way through a maze of narrow-ridged mountains and steep-sided valleys. Wilderness Road travelers forded rivers, confronted rugged rock outcrops, cleared thick stands of cane (bamboo) and dense growths of laurel and rhododendron, and struggled against the worst of weather.
Methodist Bishop Francis Asbury traveled the Wilderness Road in 1793 and wrote in his journal: “What a road! Certainly the worst on the whole continent, even in the best weather; yet bad as it was, there were four or five hundred crossing the rude hills … men, women and children, almost naked, walking along bare-foot and bare-legged, laboring up the rocky hills, whilst those who are best off have only a horse for two or three children to ride.” Travel along the Wilderness Road wasn’t for the weak or faint of heart.
A discussion of the Wilderness Road must begin with Daniel Boone, who, over the years, has become Kentucky’s most famous symbol of the frontier spirit. Boone was an experienced frontiersman and knowledgeable hunter, and he thought nothing of being away from home for as long as two years at a time. That’s why he and many other professional hunters were called “longhunters.” There was a tremendous abundance of buffalo, deer, elk, wolves, bears, wild turkeys and owls in Kentucky for them to pursue. As a result, hunters could become wealthy selling furs and hides to East Coast and European merchants. Their greatest challenge was making sure they had enough ammunition and packhorses to keep them in business.
I’ll never understand why any woman would have agreed to marry Boone, except that Rebecca Bryan was herself a child of the frontier. Boone and Bryan first met deep in a dense forest around dusk, when Boone almost shot her, thinking that he was aiming at a wild animal. Bryan screamed and fled. Horrified by what he had almost done, Boone immediately sought out the Bryan home and apologized to the traumatized girl and her family. The apology apparently was accepted because, following a courtship, Daniel and Rebecca were married. Given Boone’s risky lifestyle and countless close calls, it is hard to believe that he died of natural causes at the ripe old age—for that era, at least—of 85.
Boone was a natural choice when the Transylvania Land Company decided to hire someone to blaze a 90-mile trace, as trails were called back then, from the Cumberland Gap to a new settlement on the south side of the Kentucky River—today’s Fort Boonesborough, near Richmond. Boone, along with 30 woodsmen he recruited, created the trail that became the Wilderness Road.
Even though historians have pretty much identified the route of the original Wilderness Road, it can be hard to find. During the 225 years since it was created, it has been neglected, rerouted and covered up. Boone may have been responsible for blazing the Wilderness Road, but he would have a harder time finding it today than he did in 1767, when he took a wrong turn and ended up near the West Virginia border. As he explained, “I can’t say as ever I was lost, but I was bewildered once for three days.”
THE CUMBERLAND GAP
As Kentucky Monthly readers likely have figured out, I enjoy riding my bicycle across the Commonwealth. The more I read about the Wilderness Road, the more intrigued I became with the idea of biking as much of the original route as possible and learning what I could about the people who traveled it and settled the Commonwealth.
My Wilderness Road bike ride began on U.S. 25E a mile south of Middlesboro at the Cumberland Gap National Historical Park. The park visitors center provides interesting displays, descriptive movies, books and maps, and knowledgeable park rangers. As one ranger told me, “Visitors greatly enjoy learning about the settlers who poured through the Gap between 1775 and 1810. These were determined and brave folks. A few rode horses through the Gap and into Kentucky, but most walked. Even though the Cumberland Gap was a greatly welcomed 600 foot ‘notch’ in the Alleghenies, the route across the Gap was still so steep and treacherous that travelers called it the ‘Devil’s Stairway.’ ”
The trailhead for those who traveled the Wilderness Road into Kentucky is a few miles south of the Cumberland Gap Tunnel near Cumberland Gap, Tennessee. American Indian ambushes along the road were so frequent in the late 18th century that travelers would wait for days on the Tennessee side of the Gap, until a sizable group with sufficient guns and ammunition had formed and it was thought to be safe to proceed.
Every Kentuckian should experience driving through the 4,600 foot-long Cumberland Gap Tunnel. Completed in 1996, it is a magnificent engineering feat that took five years to construct. Bicycles are not allowed in the tunnel, but a member of the Tunnel Authority kindly put my bike and me in his truck and dropped us off on the other side so I could view the Wilderness Road trailhead.
After visiting the Cumberland Gap National Historical Park, I biked the challenging climb to the nearby 2,440 foot-high Pinnacle Overlook, where visitors can view the impressive Cumberland Gap. It’s a magnificent panorama, and well worth the effort it takes to get there. The site must have been incredibly foreboding to Wilderness Road travelers, who could see nothing ahead of them but formidable mountains and dense forests.
I thought about this as I pedaled northward from the Cumberland Gap. Imagine the isolation of walking for hundreds of miles, advancing a few miles each day, while seeing nothing but a vast, mountainous wilderness. Imagine hiking over steep, narrow, often muddy and hazardous pathways. Imagine being completely dependent upon the land and rivers for your food. Imagine being severely underdressed and ill-equipped, having fled economic hardships and religious persecution in Europe in search of a more prosperous life that might lie ahead if one were fortunate enough to reach central Kentucky. These were brave and hardy souls.
Due to their dire circumstances and the illiteracy of most 18th-century travelers, few personal diaries are to be found. One, written by Moses Austin, a merchant from Connecticut, stated: “I cannot omit Noticeing the many Distressed families I passed in the Wilderness nor can any thing be more distressed to a man of feeling than to see women and Children in the Month of December Travelling a Wilderness Through Ice and Snow passing large rivers and Creeks with out Shoes or Stocking, and barely as maney rags as covers their Nakedness, without money or provisions except what the Wilderness affords.”
When I wondered why pioneers traveled the Wilderness Road during late fall or winter, I was told that bare trees made it easier to see the wilderness and dangers that might be lurking there and that crossing frozen rivers was less dangerous than crossing a flowing river.
In 1783, Capt. James Trimble and his family, who seem to have been well-to-do, left Virginia for Kentucky in search of the land Trimble had been awarded for service during the Revolutionary War. Their trip over the Wilderness Road was described by Trimble’s wife, Jane: “In September, a company was formed, consisting of eight or ten families … all rode upon horses with farming and cooking utensils, beds and bedding, wearing apparel, provisions, and last but not least, libraries, consisting of two Bibles and the Catechism … Each man and boy carried his rifle and ammunition, and each woman her pistol, for the long journey was mostly through a wilderness.”
The Wilderness Road was a dangerous place. Hundreds of travelers, probably even thousands, died of illness or were killed by American Indians and thugs. The history of the westward surge of immigrants into Kentucky is written in the hundreds of unmarked graves that lie by the side of the Wilderness Road. There was so much death that I found myself wondering how pioneers dealt with their constant grief and sense of loss. This question was answered—at least in part—when I came upon a diary that included this poignant entry: “On the morrow we shall bury them. We shall weep for them as we have for all those who have died before. But we must go on living, and one day we shall overcome this perilous wilderness.”
HEADING TO THE ‘CROSSROADS OF THE WILDERNESS’
Continuing north on U.S. 25E, my bike and I closely followed the original Wilderness Road to Pineville, Barbourville and London. Cumberland Gap receives all the credit, but 14 miles north—in what is today Pineville—is another gap, where the Cumberland River cuts through Pine Mountain. It permits easy passage at river level. Without the Pine Mountain Gap, pioneers would have moved north through the Cumberland Gap only to encounter a formidable barrier and topographical dead end a day or two later.
It was then on to Barbourville, where I stopped at the town square to enjoy the magnificent life-sized bronze statue of Daniel Boone that stands in front of the Knox County Courthouse. Don’t miss it.
U.S. 25E is a busy highway that isn’t friendly to guys on bicycles, so I was pleased to learn that Ky. 229 from Bailey’s Switch (north of Barbourville) to the Levi Jackson Wilderness Road State Park south of London follows the original Wilderness Road. Biking Ky. 229 feels a lot like what the original route must have been like: a hilly, tree-canopied, narrow, winding country road that runs next to a lazy, meandering river. Biking Ky. 6 from Barbourville to Corbin provides the same experience.
Levi Jackson Wilderness Road State Park near London includes a Mountain Life Museum that recreates a pioneer settlement and McHargue’s Mill, a working reproduction of an early 19th-century mill. Visitors also are treated to the largest display of millstones in the country. Plus, there’s a large campground and an old cemetery where more than 20 victims of the McNitt family were killed in a 1786 massacre by American Indians and are buried. Of great interest are the park’s many miles of hiking trails, which include two trails totaling 8½ miles that are said to have been part of the original Wilderness Road.
Eight miles north of London on Ky. 490 is an area named Hazel Patch that Boone and others called the “Crossroads of the Wilderness.” Hazel Patch earned its unique name because hazel nut trees abounded in the area and produced a fruit on which small animals fed. This, in turn, attracted plentiful game to the site, making it a favorite of hunters. When the fruit was ripe, hunters and travelers would fill bags with nuts and carry them for nourishment.
ON TO FORT BOONESBOROUGH
The Little Rockcastle River winds its way through Hazel Patch and is where travelers would camp overnight and replenish their water supplies. A historical marker describes the site. It was called the “Crossroads” because from Hazel Patch, the Wilderness Road sprouts two spurs. One spur is known as Boone’s Trace, and was never more than a steep, rocky, muddy path suitable only for packhorses and people on foot. It splits off to the north for 45 miles to Fort Boonesborough and the Kentucky River. This is part of the 90 miles of paths that Boone and his party of woodsmen blazed for the Transylvania Land Company in early 1775.
A mile up the road from Hazel Patch on Ky. 490 is the Mt. Carmel Christian Church. The Wilderness Road passed a couple hundred feet behind the church. Johnny Lewis, judge-executive of Laurel County from 1980-88, happened to be attending a community picnic when I arrived at the church. Lewis showed me where the Wilderness Road had been, and then cautiously opened a wide, swinging gate into a cow pasture and led me to an area where the Wilderness Road travel had worn a rut in the terrain.
Continuing on Ky. 490 and the Wilderness Road past the Camp Wildcat Civil War Battlefield to Mt. Vernon, I biked U.S. 25 to Berea and Richmond, and then over scenic Ky. 388 straight into Fort Boonesborough and the Fort Boonesborough State Park. Both places are well worth visiting. You can learn about Kentucky’s early history and stand in front of a successor of the “Divine Elm Tree,” under which the first Kentucky legislative session and the first religious service west of the Allegheny Mountains took place in May 1775.
Fort Boonesborough has been wonderfully reconstructed as a late 18th-century working fort, complete with cabins, blockhouses, stockades and era furnishings. Knowledgeable living history guides, dressed in period clothing, demonstrate aspects of the era’s life and work. Remarkable attention is paid to detail and historical accuracy. Outside the fort, a striking monument honors the more than 600 people who lived within the walls of one of Kentucky’s earliest settlements.
Pioneers didn’t like being crowded but ended up seeking sanctuary in forts such as Boonesborough when life outside became too fraught with danger. In 1779, the Boone family fled Fort Boonesborough, which, in their opinion, had become too crowded. With several other families, they moved 12 miles away and built a new settlement, Boone’s Station, near the town of Athens. Scholars have discovered that when neighbors got as close as 5 miles, settlers felt crowded. It is estimated that 60-80 percent of frontier families, like the Boones, moved to less populated areas within a decade of arriving on the Wilderness Road.
Having finished visiting Boonesborough and feeling hungry, I pedaled a scenic couple of miles to the nearby Hall’s on the River Restaurant. Hall’s was established at its current site on the Kentucky River in 1783 as Holder’s Tavern. It’s fun to sit on Hall’s large outdoor deck and imagine what it was like 234 years ago to walk into a tavern set in the middle of an isolated wilderness and order a homemade brew and—just guessing—a roasted elk sandwich. Capt. John Holder, who established the tavern, is also famous for having rescued Daniel and Rebecca Boone’s daughter, Jemima, and her friends, Elizabeth and Fanny, following their capture by a band of Shawnee. Holder built Holder’s Tavern a few years later, after he had married Fanny.
Part II of Kirk Alliman’s travels on the Wilderness Road will appear in the February issue of Kentucky Monthly.