The Stunning Kentucky Gap that Became America’s Front Door West in 1775

Cumberland Gap National Historical Park, Kentucky

Before there were interstates, there was Daniel Boone. His Wilderness Road became the pipeline that poured settlers into Kentucky and beyond, reshaping a continent.

Here’s how it all started at this beautiful, historic park you can visit today.

Richard Henderson Forms The Transylvania Company

North Carolina judge Richard Henderson started the Transylvania Company to create a new colony in Kentucky. In March 1775, he met with Cherokee leaders at Sycamore Shoals to buy their land.

Henderson paid 10,000 pounds of goods for 20 million acres between the Cumberland and Kentucky rivers. Virginia’s governor later canceled this deal, saying Henderson had no right to buy the land.

Henderson needed someone who knew Kentucky to mark a clear path for settlers. Daniel Boone was perfect since he had explored Kentucky since 1769.

Woodsmen Gather For The Journey

Boone picked 30 skilled axemen at John Anderson’s Blockhouse on March 10, 1775. His brother Squire and son-in-law joined him on this historic trip.

Other men included Michael Stoner, Richard Callaway, William Bush, David Gass, and Felix Walker. Walker kept a journal and wrote that all men agreed to follow Boone through the wilderness.

Each man brought axes for cutting trees, rifles for protection and hunting, and basic supplies. They needed strength and courage to face the unknown dangers ahead.

Ancient Paths Form The Foundation

Boone followed parts of trails that already existed instead of making completely new paths. Native Americans had used the Great Warrior’s Path for hundreds of years before Boone.

Buffalo herds first created these routes as they walked to salt licks. Cherokee and Shawnee tribes later used these paths, calling the route ‘Athowominee’ or ‘Path of the Armed Ones.’

Dr. Thomas Walker found the gap in 1750 and named it ‘Cave Gap.’ Boone first traveled here in 1769 with John Finley, learning about landmarks that helped him during his 1775 trip.

Marking Trees And Clearing Paths

Boone’s team used axes to cut small trees and clear thick brush blocking their way. They left large trees standing but cut off strips of bark to create pale marks called ‘blazes.’

These blazes formed a line of markers showing future travelers which way to go. The path was only wide enough for people walking or on horseback, not for wagons.

Boone chose the most direct route using existing trails. Clear markers were vital since getting lost in this wilderness meant possible death from hunger, weather, or hostile encounters.

Journey Begins At The Long Island

The trip started at Long Island of the Holston River, a Cherokee meeting place where Kingsport, Tennessee stands today. From there, the men headed north along the Great Warrior’s Path.

They went through Moccasin Gap, a natural break in the Clinch Mountains. The team avoided Troublesome Creek, known for dangerous flooding.

They crossed the Clinch River near present-day Speers Ferry, Virginia. This first part of the journey set the pattern of using natural features to overcome difficult terrain while saving energy for bigger challenges ahead.

Moving Through Mountain Passages

After crossing the Clinch River, the men followed Stock Creek deeper into Virginia. They faced Powell Mountain next and found their way through the narrow pass called Kane Gap.

From there, they went down into Powell Valley and reached Martin’s Station, about 20 miles east of Cumberland Gap. Joseph Martin had built this outpost in 1769 but left after Native American attacks.

Martin had just returned in early 1775 to rebuild before Boone arrived. This station gave Boone’s tired men a brief rest before tackling Cumberland Gap.

Passing Through Cumberland Gap

Cumberland Gap was the key challenge of the journey. This V-shaped cut through Cumberland Mountain rises about 300 feet above the valley floor.

Boone’s men used the ‘saddle’ of the gap, its lowest point where thousands of settlers would later cross. White rock cliffs on top of Cumberland Mountain served as a landmark visible from far away.

This gap was the main break in the 600-mile Appalachian Mountain chain. Without this natural passage, Kentucky settlement might have been delayed for years.

Shawnee Warriors Attack

On March 24, 1775, Shawnee warriors attacked Boone’s camp at dawn when they were just 15 miles from their goal. The warriors rushed in with tomahawks while the men slept.

Several men died and others were hurt, but most escaped into the woods. The Shawnee had never agreed to sell their Kentucky hunting grounds and saw Boone’s party as invaders.

Boone gathered his surviving men and drove off the attackers. After the fight, he built a temporary wall using logs stacked 7 feet high to protect his wounded men.

Fort Established On Kentucky River

Boone’s group reached the Kentucky River in April 1775 despite the Shawnee attack. They picked a spot on the south bank in what is now Madison County.

They began building a settlement that would become Fort Boonesborough. Richard Henderson arrived on April 20 with more settlers, having followed Boone’s newly marked trail.

Henderson named the fort after Boone to honor his work. Fort Boonesborough became one of Kentucky’s first permanent settlements along with Harrodsburg and Logan’s Station.

Wilderness Road Changes America

About 300,000 settlers traveled Boone’s Wilderness Road into Kentucky between 1775 and 1810. This movement of people changed the American frontier forever.

Kentucky became a state in 1792, just seventeen years after Boone marked the trail. For twenty years, his path remained narrow, only usable by foot or horse.

Workers widened the road in 1796 so wagons could use it. The Wilderness Road remained the main route into Kentucky until the 1840s.

This single path through Cumberland Gap sped up western settlement by decades.

Visiting Cumberland Gap National Historical Park

Cumberland Gap National Historical Park is located at 91 Bartlett Park Road, Middlesboro, KY 40965. The park visitor center is open daily from 9:00 AM to 4:00 PM, closed only on Thanksgiving, Christmas, and New Year’s Day.

You can start your visit at the main visitor center where exhibits tell the story of Daniel Boone’s 1775 expedition. Don’t miss the 23-minute film ‘Daniel Boone and the Westward Movement’ shown in the upstairs theater.

Admission to the park is free. Walk the original Wilderness Road Trail to experience the same path Boone and his axemen blazed.

From the Daniel Boone parking area, you can hike part of the historic Boone Trace. For spectacular views, drive the 4-mile road to Pinnacle Overlook where you can see three states.

For a guided experience, join the Gap Cave tour ($8 for adults, $4 for seniors and children 5-12) where you’ll walk along the historic Wilderness Road to the cave entrance. Call 606-248-2817 to reserve your spot up to one month in advance.

The park offers over 85 miles of hiking trails. The Boone Trail connects the Wilderness Road Campground and the Daniel Boone parking area.

Visit during spring and fall for the best weather and views.

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