“It was on the first of May,
in the year 1769, that I resigned my domestic happiness for a time, and left my family and peaceable habitation on the Yadkin River, in
North-Carolina, to wander through the wilderness of America, in quest of the country of Kentucke.”

So began the narrative of Daniel Boone’s first adventure beyond the Cumberland Gap as written in 1784 by his earliest promoter, John Filson.

Cumberland who?

When Dr. Thomas Walker explored in 1750 what is today Kentucky, he came across a strong river at today’s Pineville and named it the Cumberland River in honor of Great Britain’s Duke of Cumberland. He was the second son of King George II and the victor over the Scots at the Battle of Culloden in 1747. Dr. Walker admired the man. In time, what Dr. Walker called “Cave Gap” became known as the gap to Cumberland River and soon enough as “Cumberland Gap.”

Historic View of “Ken-te-ke”

Pilot Knob State Nature Preserve in Clark County, Kentucky, offers hiking trails to the historic overlook from which Daniel Boone first viewed “the beautiful level of Kentucky” on June 7, 1769. (Caution is advised. This overlook has no railing or safety fences.) June 7 is Boone Day, established by the Kentucky Historical Society about 150 years ago.

Cumberland Gap—that fabled portal through the Appalachian Mountain barrier—was the passage through which arose America’s great westward movement. A quarter of a million westering settlers and more passed through that notch during the third of a century after the American Revolution began in 1775 at Lexington and Concord, communities connected inseparably to Colonial life along the Atlantic seaboard. Those pioneering emigrants in the backcountry, however, were heading west with all the hopes and ambitions such a promising frontier engendered. With courage and determination, they passed through that natural gateway and into the Kentucky wilderness. They did so along the storied Boone Trace until 1796 and thereafter mostly along the separate Wilderness Road. But, a mere six years before that auspicious beginning of America’s first reach toward a transcontinental footprint, America’s pioneer hero Daniel Boone first laid eyes upon the majestic Cumberland Gap. The year was 1769—a notable 250 years ago—the year Daniel Boone began a memorable two-year adventure in the wilds of Kentucky. It most certainly would not be his last.

 By 1769, Daniel Boone had lived in North Carolina for 17 years since arriving from Pennsylvania by way of Virginia with his parents in 1752. At the age of 18, he settled with them in the Forks of the Yadkin (today’s Davie and Yadkin counties). He married Rebecca Bryan four years later, and after surviving the perils and dislocations of the Cherokee War and later becoming lost in the swamps of north Florida, he moved his family in 1766 to the reaches and banks of the Upper Yadkin River. He built cabins along the foot of the Blue Ridge Mountains, in today’s Wilkes County, for this family, at the time, of two sons, three daughters, and two nephews. He hunted on the Blue Ridge plateau of today’s Watauga County, whose county seat bears his name—Boone.

In the winter of that year, a fellow wagoner during Boone’s French and Indian War experience, John Findley (Finley, Findlay), came to the North Carolina backcountry in search of Daniel and to convince him to try a new way through the mountains into the land of “Ken-te-ke.” Findley had traded with the Shawnee there a decade before by canoeing down the Ohio River. Boone jumped at the opportunity, having only a year before been forced to winter-over in the hills of eastern Kentucky after being trapped by an early snowstorm. He had entered Kentucky then through the rugged mountains along the winding Russell Fork of the Big Sandy River. Findley’s notion of finding a dry gap of easier passage through the mountains appealed to Boone immediately even if Findley was not sure how to find it.

Into the Land of Ken-te-ke

On May 1, Daniel Boone, then 34, rode westward in search of this rumored passage into Kentucky. With him were John Findley, his brother-in-law John Stuart, and three other men to work as camp keepers. These market hunters planned to hunt for deer and to sell the skins back in Salisbury, North Carolina. They expected to turn a good profit on the hides, which were in high demand in Europe because of a leather shortage.

 Daniel thought he was heading deeper into a wilderness than white settlers had ever ventured, save a few adventurous sorts. Long hunter Elijah Wallin, who had passed through the gap in 1763. Thus, Boone was genuinely surprised to come upon Joseph Martin and his party of men building a station deep in the forests. They were only some 15 miles ahead of the pass then known as Cave Gap. Martin intended this outpost to serve as a supply station. He had arrived there in late March ahead of a rival party in a contest to settle first in Powell Valley. They competed for 21,000 acres from Dr. Thomas Walker and the Loyal Land Company. It was Dr. Walker who in 1750 first brought word back east of Cave Gap, an easy passage through the mountains.

 During late May and early June 1769, Boone’s party passed through the magnificent gap in the Cumberland Mountains and entered into Kentucky. The passage is an ancient water gap pushed upward over eons with a towering rockface on the north side. The path through that passage had been trod for millennia by herds of seasonally migrating bison and deer. It was a route followed by Shawnee, Cherokee, and Yuchi as well as unnamed ancient native peoples who traversed the land for thousands of years. Indeed, before Boone’s arrival and even Walker’s “discovery,” the route through the pass was known as the Warrior’s Path—Athiamiowee, “path of the armed ones.”

 The Beautiful Level of Kentucky

Call out: [O]n the seventh day of June following, we found ourselves . . . where John Finley had formerly been trading with the Indians, and, from the top of an eminence, saw with pleasure the beautiful level of Kentucke.  – The Adventures of Col. Daniel Boon by John Filson, 1784.

 In early June, Boone’s party reached the region where John Findley had previously traded at the Shawnee town Eskippakithiki. The explorers walked up a promontory and from there on June 7, 1769, first saw the beautiful expanse of the bluegrass region of Kentucky stretching before them.

The men immediately set about the business of hunting deer and preparing hides. They set up a base camp from which they ventured out in pairs  to explore and to hunt. They set up satellite camps for processing deer skins, graining them and packing the prepared hides into bundles of about 40 skins, each bundle weighing close to 100 pounds. A pack horse could carry only two such bundles on the long trek home.

With only themselves for company, the men shared tales around the evening fire and Daniel Boone read to them from Jonathan Swift’s Gulliver’s Travels, the first book brought into Kentucky. Inspired by the stories they heard, one of his illiterate hunting companions called a creek by a name from the book as best as he could remember it—“Lulbegrud” for Lorbrulgrud, Swift’s fictional metropolis, the capital of Brobdingnag. That creek in today’s Clark and Powell counties, Kentucky, retains that name.

 Yellow Jackets Will Sting You

Boone’s party kept at their market hunting through the summer and fall, but in late December, Boone and Stuart were discovered by a party of Shawnee hunters returning to their home villages across the Ohio River. They were led by Will Emery, a mixed-blood Cherokee by some accounts. Neither the Shawnee nor the Cherokee lived on the Kentucky lands. This was their hunting land—their store house—where undisturbed nature provided its bounty for them to hunt and kill as they needed food. “Captain Will” and the Shawnee regarded Boone and his men as poachers. They forced Boone and Stuart to take them to each of their station outposts in succession. Boone did so slowly and while making as much noise as possible, hoping to alert his companions at the other camps to remove the bundles of hides. So, Boone was doubly disappointed to discover at the base camp that his companions had run off and had left all the skins behind.

Captain Will confiscated all the hides. He took Boone’s and Stuart’s horses and rifles, giving them a simple trade gun and a small amount of shot and powder to kill enough game to feed themselves. He also gave them two pairs of moccasins each and told them to leave. “Now, brothers, go home and stay there,” he said. “Don’t come here anymore, for this is the Indian’s hunting ground, and all the animals, skins and furs are ours; and if you are so foolish as to venture here again, you may be sure the wasps and yellow-jackets will sting you severely.”

 Steal Horses, eh?

Boone and Stuart were not so easily dissuaded. On foot, they tracked the departing Shawnee, knowing they would be slowed some by the amount of booty they were carrying. After two days, they crept into the Indian camp at night to recover several horses. They rode all the next day before they stopped, but they were almost immediately overtaken by an angry Captain Will and a dozen warriors who had ridden all night. They placed a bell—one used to locate grazing horses—around Boone’s neck and forced him to dance around as they chided in broken English, “Steal horses, eh?” Boone and Stuart were then taken as prisoners and forced to travel with the party north.

During a seven-day march toward the Ohio River, Boone lulled the captors into a sense of complacency by appearing to be cooperative. But, early in the evening of the seventh day, as the sun was setting and as the Shawnee were busily setting up camp and tending to the horses, Boone and Stuart saw their chance. They nodded at each other and sprang for the rifles, shot, and powder that had been carelessly laid aside near them. They scampered into a thick canebrake, where they hid quietly until the fading light made it impossible for the Shawnees to find them. Crawling quietly, they hurried along in the dark; and, avoiding the Warrior’s Path, they covered in 24 hours on foot the distance the Shawnees had taken seven days to ride.

 The Initials “JS”

Upon their return to Station Camp, the two men realized their fellow hunters had abandoned the camp station completely. The embers in the campfire told Boone that Findley and the others had not been gone long. Boone and Stuart, though exhausted from their ordeal, immediately pursued the other hunters. Within 40 miles, they found their party camped near the Rockcastle River. There, Boone was surprised and delighted to find his brother Squire. He had come from the upper Yadkin River settlement in North Carolina after harvesting the fall crops. He had been on his way to meet Boone with horses, traps, ammunition, and other supplies when he had met the retreating men on the trail. To this great fortune for Daniel was added the arrival of another companion, Alexander Neely, whom Squire had recently met in the New River valley. The two men were eager to join with Daniel and Stuart, who were mightily encouraged by this turn of events. 

The four men moved their camp station to a spot on the north bank of the Kentucky River and began their winter hunt by trapping beaver. To help out, they built a canoe. Still hunting as a pair, Daniel and Stuart took opposite sides of the Kentucky River in early February 1770 with plans to meet up days later. When Stuart did not arrive as agreed, Daniel crossed the river and discovered Stuart’s camp with the initials “JS” carved in a tree, but he could not find Stuart. Daniel was deeply saddened at Stuart’s disappearance. About age 26 at the time, he was not only a good friend and hunting companion but the husband of Daniel’s younger sister, Hannah, and a father to three children.

In time, Squire and Neely returned to the camp and learned from Daniel of Stuart’s disappearance. The news so unsettled Neely, that he immediately left the frontier and returned east alone. Daniel and his brother continued trapping. They were not molested by Indians during the remaining winter months or the early spring. During that time, they had good success but ran low on supplies and ammunition. On May 1, 1770, Squire packed up their pelts and returned to the Yadkin River valley to settle debts and to restock their provisions. Meanwhile, with only a little ammunition in his possession and with no horse or dog for company, Daniel remained in Kentucky alone. Ever the adventurer, Daniel Boone was eager to explore even farther afield the promising wilderness areas of Kentucky, those lying far beyond the Cumberland Gap.   

One day I undertook a tour through the country, and the diversity and beauties of nature I met with in this charming season, expelled every gloomy and vexatious thought. . . . I had gained the summit of a commanding ridge, and, looking round with astonishing delight, beheld the ample plains, the beauteous tracts below.

—The Adventures of Col. Daniel Boon by John Filson, 1784