Through the Cumberland Gap

[“Daniel Boone Escorting Settlers through the Cumberland Gap” by George Caleb Bingham, 1852]

For their first few generations, English colonists continued to think of themselves in relation to the ocean, with all its connections to home and to the rest of the world. But with time and the spread of the areas of settlement, the settlers of western Pennsylvania, and Virginia, and North Carolina, increasingly looked not east, but west.

For decades, pioneering families moved from the Pennsylvania Dutch country down the long Shenandoah valley through Maryland and Virginia, and some of them wound up in North Carolina. (In this way, North Carolina, a state with few good natural harbors, was actually settled as much west to east as east to west.) They wanted to keep moving West rather than farther South, to stay in the latitudes they were used to. But to the West were the Appalachians. Before highways and the internal combustion engine; before railroads powered by steam; before unpaved roads traversed by horse and wagon, those mountains formed a solid barrier hemming in frontier families who were looking for a little elbow room.

In the mid-1700s, unpaved roads were dusty in dry weather, muddy in wet, and rutty and potholed always. And that was on flat land! Passages across broken land were difficult, often impossible, for carriages and wagons. Seaboard America didn’t put a lot of time or money into improving its roads, since travel by river and sea was so much cheaper and easier. But once the line of settlement moved beyond the rivers, travel and commerce depended on roads, and roads depended on terrain.

Nearly the entire length of that old mountain range was far too high and too rugged for the technology of the day to run roads through it. To run a road over the mountains, you’d need to find an interruption in the wall that would let you thread through the barrier to get to the promised land.

Surely there was such a way over the Appalachians. There had to be!

There was. It was (and is) located more or less where the modern-day states of Virginia, Kentucky and Tennessee come together. In the year 1750, a Virginia doctor named Thomas Walker pointed it out and named it, and in time the Cumberland Gap became the gateway to the West.

Walker found the gap, but the man who did more than anyone else to open the way to Kentucky was a man named Daniel Boone.

Daniel Boone was born in 1734, two years after George Washington, of Quaker parents, on the edge of the Pennsylvania frontier. The Pennsylvania Quakers had good relations with the Indians, and young Boone learned woodcraft as much from the Lenape Indians as from the local white settlers. (He was given his first rifle at the age of 12 to provide food for the family.) In 1750, when Daniel was 16, his father moved the family to western North Carolina.

Because he grew up on the frontier, Boone, like Abraham Lincoln two generations later, had little formal education, and like Lincoln he was literate and enjoyed reading. In later years, he would bring books with him on his long hunting expeditions, sometimes entertaining his companions by reading to them around the evening campfire. But unlike Lincoln, who was born 75 years later, Boone never had much to do with cities or even towns. He was acknowledged as an unexcelled master of the woods. (Late in life someone asked him if, in his extensive solitary travels,  he had ever gotten lost. He said, no, he wasn’t ever lost, “but I was bewildered once for three days.”)

Like the young George Washington, Daniel Boone served with the British military during the French and Indian War. In fact, in 1755, he was a wagon driver with the same expedition that young Washington narrowly saved from total disaster after the British general was killed. Oddly enough, one of the most important results of that failed expedition was that a wagon driver named Daniel Boone had his imagination caught by the tales he heard from another driver named John Finley, who had been across the mountains, trading with the Indians in a place they called Kentucky. Nothing happened just then: Boone went home and the following year married. But the seed had been planted.

For years, Boone supported his family as a commercial hunter, going alone or with a few others into the wilderness, hunting and trapping for weeks or months along what were called the Medicine Trails (buffalo migration trails), then returning to sell the hides and pelts. But by the mid-1760s, colonial immigration into the Yadkin valley area had made it harder for a hunter to find enough game to make ends meet. Time to move.

He thought about moving to the Pensacola, Florida area, and actually bought some land there, but his wife refused to move so far from everything she knew. Not Florida? Well, then, where? And then fate stepped in again, and here was John Finley visiting, still with his tales of Kentucky.

Boone first reached Kentucky in the fall of 1767 while on a long hunt with his brother. At some point he learned that the feared Iroquois Indians had signed the Fort Stanwix treaty, ceding Kentucky to the British. In May, 1769, Boone began a two-year hunting expedition in Kentucky, but in December, he was captured by Shawnees, who had not signed the Fort Stanwix treaty. They regarded Kentucky as their hunting ground. They confiscated all the skins and told Boone and his companion to leave and never return. But Boone continued hunting and exploring Kentucky, and in September, 1773, he led a group of about 50 would-be emigrants to establish a settlement in Kentucky. The attempt was abandoned after one of his sons, and another man, were captured by a band of Delaware, Shawnees, and Cherokee Indians, and tortured to death. That massacre led to what was called Dunmore’s War between Virginia and the Shawnees, which ended in the Shawnees relinquishing their claims to Kentucky. And in 1775, a North Carolina judge named Richard Henderson hired Boone to blaze what became known as the Wilderness Road through the Cumberland Gap.

Boone led a party of 30 into central Kentucky, marking a path to the Kentucky River and founding Boonesborough. He brought his family there on September 8, 1775, when he was 49 years old. The road he marked, and the settlements he founded and protected, are the reason that Kentucky had enough inhabitants in 1792 to be admitted to the Union as the first state west of the Appalachians, eleven years prior to the admission of Ohio.


Daniel Boone had a lot more life to live, but the story is too long to tell here, and too interesting to make short work of. He served as an officer of militia in the Revolutionary War, fighting in the 1782 Battle of Blue Licks, which was one of the last battles of the war, fought after the surrender at Yorktown. He continued pioneering, and became a legend in his own lifetime, famous not only in America but in Europe. He died of natural causes on September 26, 1820, nearly 86 years old. By the time he died, the wilderness road had enabled an estimated 300,000 men, women and children to get past the mountain barrier.


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