In the spring of 1775, Daniel Boone and 30 woodsmen spent less than a month marking a 200-mile trail that passed through the Appalachian Mountains at Cumberland Gap on its way from Virginia to Kentucky’s Bluegrass Region. More than two centuries later, workers constructed twin mile-long tunnels beneath the rock of this historic pass. The tunnels opened in October 1996 and cost $250 million. Boone, historians believe, never got paid for his roadwork.

During the years between Boone’s trail marking and the tunnels, history has left deep tracks at Cumberland Gap. In the late 1700’s, 200,000 pioneers passed through this gateway as they helped move the American frontier west. Civil War activity and a brief industrial boom in he late 1800’s added to the long line of the famous and ordinary who journeyed through the pass. Union General, Ulysses S. Grant and legendary frontier hero George Rogers Clark traveled the gap. So did Abraham Lincoln’s parents and grandparents as they emigrated west.

Today, visitors to this scenic region, a corner of southern Appalachia 80 miles northeast of Knoxville, Tennessee, can retrace the footsteps of those earlier frontiersmen, settlers and soldiers while exploring and visiting the quiet town that shares the gap’s name. Drive the four-mile Pinnacle Road from the visitor center to the mountaintop overlook and you’ll get a magnificent view of three states-Kentucky, Virginia and Tennessee-and the town of Cumberland Gap, 1,200 feet directly below. Artwork near the overlook parking area bears a quotation from nineteenth-century historian Frederick Jackson Turner, who called the gap a place to stand and "watch the procession of civilization, marching single file…"

That procession began with the Indians who followed an ancient buffalo trace through the pass. In the mid-1600’s, white hunters started carrying news home to eastern settlements about a notch through the mountain that defined the frontier.

The earliest written record of the gap is credited to Dr. Thomas Walker, a Virginia physician-turned-explorer who traveled through the region in 1750 and noted "Cave Gap," named after a nearby cavern. Walker also named the river north of the pass "Cumberland" in honor of the Duke of Cumberland, son of Britain’s King George II. The duke was popular because of his victory over the Scots at Culloden. Eventually the name was transferred to the pass as well.

Twenty five years after Walker passed through, Richard Henderson, a land speculator and former North Carolina judge, sent Boone and his woodsmen to mark a trail through the gap for eastern settlers bound for Kentucky. Boone was already familiar with the area, having passed through the gap on hunting expeditions to Kentucky. He was also aware of the area’s dangers, especially from Indians who wanted to keep whites away form their lands. On two occasions Boone encountered Indians who took all the skins he had collected. In 1770, Boone’s friend and brother-in-law John Stewart disappeared while he and Boone were on an expedition into Kentucky. For five years Stewart’s fate remained a mystery, until a worker on Boone’s Wilderness Road expedition found a skeleton with a powder horn bearing Stewart’s initials. Boone suffered another personal loss in 1773 when he attempted to establish a settlement in Kentucky. Indians attacked part of the expedition near the gap and killed several people, including Boone’s son James.

Boone’s trail marking wasn’t his first association with Henderson. The land speculator had once sued the frontiersman for unpaid debts and had sworn out a warrant for his arrest. Apparently, it had all been smoothed over by the time he hired Boone. Henderson had negotiated 20 million acres of Kentucky and Tennessee land away form the Cherokee Indians as part of a plan to establish his own colony of Transylvania, with its capitol at the newly formed settlement of Boonesborough. His plan eventually failed, mainly because the legislatures of Virginia and North Carolina protested that the land belonged to them.

When Henderson’s scheme collapsed, Boone’s promised compensation disappeared with it. His work on the old Indian path, however, firmly established the route that would become known as the Wilderness Road-the "interstate" of its day, moving people from eastern Pennsylvania, Virginia and the Carolinas westward through the gap to Kentucky and beyond.

With the trail wide enough only for packhorses, the journey through the Cumberland Gap was difficult and dangerous. During the summer and fall of 1784, renegade Cherokees killed more than 100 travelers on the Kentucky side of the gap, so early settlers learned to travel in large groups for safety. One of the largest groups, numbering about 500 and including the entire Upper Spotsylvania Baptist Churh congregation from near Fredericksburg, Virginia, passed through the gap in the winter of 1781. Like others, they had to abandon their wagons, loaded with household possessions, and walk the mountain trail with only what they could carry or load on horses. The three-mile-long caravan finally crossed the gap in December, taking three weeks to cover a mere 30 miles through mud, snow and flooded streams. Not until 1796 was the Wilderness road widened enough for wagons, and by the early 1800’s Kentuckians were driving long lines of horses and cattle through the gap to markets in the east.

Visitors today can get a taste of what the Wilderness Road was like by walking nearly a mile of the original-a steep, wooded trail that begins one block form the main intersection in the town of Cumberland Gap and continues up the gap itself.

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