Everyone knows America’s legendary origins — 13 colonies fighting off the tyranny of the British Empire to form our Union — but did you know there was, if only for a brief time, an extra-legal 14th colony? If that blows your mind, you’ll be even more astounded to find out its name … it was called Transylvania.

It was made possible by a famous name, too, a man called Daniel Boone. On this episode of America’s National Parks, The Transylvania Purchase, a land which laid its gateway at a gap in the Allegheny Mountains, now known as Cumberland Gap National Historical Park, where the borders of Kentucky, Virginia, and Tennessee meet.


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Learn More

Links to some of the resources we used and the website links we mentioned in this episode. 

Cumberland Gap National Historical Park – National Park Service Website

The Cumberland Gap Tunnel – Official Website

The Wilderness Road – The History Channel

The Colony of Transylvania – The North Carolina Booklet, Vol. 3 No. 9 (Jan. 1904)


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Everyone knows America’s legendary origins — 13 colonies fighting off the tyranny of the British Empire to form our Union — but did you know there was, if only for a brief time, an extra-legal 14th colony? Actually, there were a few other colonies like Nova Scotia and East and West Florida that didn’t join the revolution and remained loyal to the crown, but I’m talking about something different. This is a colony that was created by a private company that lobbied the Continental Congress to join the union that would become the United States. If that blows your mind, you’ll be even more astounded to find out its name … it was called Transylvania. Yeah, I didn’t hear about that in school either.

In fact, had events turned a bit differently, we could be eating Transylvania Fried Chicken instead of KFC, and horses might be running the Transylvania Derby.

It was made possible by a famous name, too, a man called Daniel Boone. On this episode of America’s National Parks, The Transylvania Purchase, a land which laid its gateway at a gap in the Allegheny Mountains, now known as Cumberland Gap National Historical Park, where the borders of Kentucky, Virginia, and Tennessee meet.

A word before we begin: In this episode, we’re going to discuss treaties with indigenous people, people who already inhabited these lands, and conflicts with the so-called settlers. Clearly, people inhabited these territories long before colonizers arrived. The land wasn’t “purchased” from anybody. It was taken.

Here’s Abigail Trabue.


In the early 1700s, the Allegheny Mountains were the greatest obstacle for settlers aspiring to reach the west. In 1750, Dr. Thomas Walker, an explorer, found a cut between two mountains. A crossing that would, for centuries to come, allow passage for travelers from around the world.

Through this gap was a vast tract of lands utilized and claimed by several tribes, comprising most of modern-day Kentucky and much of Tenessee. In 1774, Richard Henderson, a judge from North Carolina, organized a land speculation company with a number of other prominent people. The company was called the Transylvania Company, and its intent was to establish a new British colony by purchasing the lands from the Cherokee, who were the primary inhabitants of much of the area and claimed hunting rights in other sections of it.

Henderson hired Daniel Boone to blaze a trail through the mountain gap, set up towns, and negotiate with indigenous people in the area. Boone had been in southeast Kentucky long before the founding of any settlements, and he traveled to the Cherokee towns to inform them of the upcoming negotiations.

In March 1775, Henderson and Boone met with more than 1,200 Cherokee at Sycamore Shoals to sign a treaty procuring all the land south of the Ohio River and between the Cumberland River, the Cumberland Mountains, and the Kentucky River — 20 million acres.

One Cherokee chief, named Dragging Canoe, refused to sign at Sycamore Shoals even though his father did. But the majority won out. Dragging Canoe left the treaty grounds taking those who were loyal to him south, eventually landing in the remote area of the Chickamauga Creek (near modern-day Chattanooga). There they established eleven towns which resisted settlers for decades. The location gave the group the name “Chickamauga.”

Henderson believed that a British legal opinion had made his private purchase of the land legal, but the Transylvania Company’s investment was in violation of both Virginia and North Carolina law, as both colonies laid claim to parts of the land. A royal proclamation also prohibited the private purchase of American Indian land and the establishment of any colony not sanctioned by the Crown. But Henderson proceeded anyway.

Daniel Boone was originally from Pennsylvania and migrated south. He was what was known as a Longhunter, someone who hunted and trapped among the western frontiers of Virginia for long periods of time. Boone would sometimes be gone for months, even years, before returning home from his expeditions. The Kentucky area was alluring to Boone because of its large salt brine lakes. Salt was essential for preserving meat on these long hunts.

Along with 35 axemen, Boone cut a 200-mile trail from Kingsport, Tennessee through the forests and mountains across the gap. It was hardly more than a path, rough and muddy.

The Shawnee laid claim to some of the land purchased from the Cherokee, but were not involved in the Sycamore Shoals Treaty. They viewed Boone and his men as invaders. While camped 15 miles from their final destination of the Kentucky River, just before daybreak, a group of Shawnee, slinging tomahawks, attacked the sleeping men. Some of the party were killed and a few were wounded, but most escaped into the woods.

When Boone reached the Kentucky River, he established the settlement of Boonesborough (near present-day Lexington, Kentucky), which was intended to be the capital of Transylvania.

The trail was difficult and dangerous. Wagons could not travel it, and still, many settlers began making the journey into the west. Entire communities would often move together over the Wilderness Road to new settlements. Many came on their own accord, refusing to recognize Transylvania’s authority. Along with regular attacks from the Shawnee and Chickamauga tribes, robbers frequented the edges of the route, seeking to pilage weaker pioneers. Defensive log structures called “stations” were built alongside the road with portholes in the walls for firing at attackers. Venomous copperheads and rattlesnakes blended into the undergrowth endangering the people and their livestock.

When Henderson was ready to enter the territory, he led another expedition of 30 horsemen following Boone’s path, widening the road so travelers could bring through wagons. Around 150 pioneers joined them along the way, including some who had been traveling ahead of them, but were retreating from Shawnee attacks further down the road. Some of the streams were flooded, and the pioneers had to swim with their horses.

When Henderson arrived at Boonesborough, just under a hundred people resided there. The settlers were living in a precarious situation. They lacked supplies and shelter, and faced significant hostilities from the Shawnee, and now the Cherokee, too, who had joined with the Shawnee and other tribes in the Cherokee-American war, which would last another 20 years. Still, Henderson urged settlers in the area to establish the colony and hold a constitutional convention.

His plan was for the various settlements throughout Transylvania to send delegates to Boonesborough. In May 1775, under a huge elm tree, a three-day convention assembled. They passed nine measures, drafting a document that built a framework of government, known as the Transylvania Compact, including executive, legislative, and judicial branches.

With that business complete, Henderson returned to North Carolina to petition the Continental Congress to make Transylvania a legally recognized colony. Virginia and North Carolina, who both claimed jurisdiction over the region, did not consent, and the Continental Congress declined to get involved.

Still, the colony existed, if not legally, until just one month before the signing of the Declaration of Independence, when the Virginia General Assembly prohibited the Transylvania Land Company from making any demands on settlers in the region.

Over 200,000 pioneers came over the Wilderness Road during this time. Many Scottish, Irish, and German. As the eastern lands were all taken, new immigrants had to push west, enduring severe hardships. Many families would walk hundreds of miles immediately after landing in America, crossing the icy creeks and rivers without shoes or stockings. One year, the weather was so cold that the Kentucky River froze to a depth of two feet. Many of the cattle and hogs froze to death. The settlers had to eat frozen livestock to survive. Often Dragging Canoe’s Chickamauga would ambush the Gap area for weeks at a time.

On July 5, 1776, Boone’s daughter and two other teenaged girls were captured outside Boonesborough by a Shawnee war party, who carried the girls north towards the Ohio lands. Boone led a group of men in pursuit, catching up with them two days later. They ambushed the Shawnee while they were stopped for a meal, rescuing the girls and driving off their captors.

Henry Hamilton, British Lieutenant Governor of Canada, began to recruit American Indian war parties to raid the Kentucky settlements. On April 24, Shawnee Indians, led by Chief Blackfish, attacked Boonesborough, and Daniel Boone was shot in the ankle while outside the fort.

While Boone recovered, Shawnees destroyed the surrounding cattle and crops. With the food supply running low, the settlers needed salt to preserve what meat they had, so in January of 1778, Boone led a party to the salt springs on the Licking River. While out hunting during the expedition, Boone was captured by Blackfish and his warriors. Boon’s party was greatly outnumbered, so he convinced them to surrender to the Shawnee.

Blackfish wanted to continue to Boonesborough and capture it, since it was now defenseless, but Boone convinced him to leave the Women and Children alone for the winter, promising that Boonesborough would surrender willingly in the spring. It was a bluff. So convincing, that many of his men thought he had turned his loyalty toward the British.

On June 16, 1778, Blackfish planned his return with a large force to Boonesborough. Boone learned of the plan and escaped, covering the 160 miles home over just five days on horseback and then by foot after his horse gave out.

During Boone’s absence, his wife and children had returned to North Carolina. Upon his return, some of the men questioned Boone’s loyalty, since after surrendering the salt-making party, he had lived quite happily among the Shawnees for months. He was even taken into one of their families and given the name Big Turtle.

To prove his loyalty, Boone led a raid against the Shawnees across the Ohio River, and then helped defend Boonesborough against a 10-day raid when Blackfish arrived in September.

After the siege, Boon was court-martialed by his fellow townspeople, some of whom still had family members held captive by the Shawnee. After Boone’s testimony, he was found not guilty, but it left him humiliated. He returned to North Carolina to get his family.

Three years after Boone blazed the Wilderness Road, In December 1778, Virginia’s Assembly declared the Transylvania claim void and took possession of the land. Henderson and his partners were given 12 square miles on the Ohio River below the mouth of the Green River as consolation – an area now known as Henderson.

Daniel Boon never returned to Boonesborough. He founded the settlement of Boone’s Station and went into business finding land for new settlers. Settlers now needed to file land claims with Virginia, and Boon would travel to Williamsburg to purchase their land warrants.

He became a leading citizen of Kentucky. When Kentucky was divided into three Virginia counties in 1780, he was promoted to lieutenant colonel in the Fayette County militia, fighting in several revolutionary war battles.

In 1781, he was elected as a representative to the Virginia General Assembly. He traveled to Richmond to take his seat in the legislature, but British captured him and several other legislators near Charlottesville. The British released Boone on parole several days later. After a term in office, he returned to fight in the war, including the Battle of Blue Licks, in which his son Israel was killed. In November 1782, Boone took part in an expedition into Ohio, the last major campaign of the war.


The word Transylvania has little to with Dracula or Eastern Europe. it merely translates to “beyond a pleasant, wooded area.”

That break in the mountains became known as the Cumberland Gap, and it is of global importance. Settlers from around the world chose to pass through it to settle the lands west of the Appalachian Mountains, along with a whole lot of slaves who didn’t have a choice. Nearly 300,000 pioneers journeyed through the nation’s first doorway to the west.

Cumberland Gap National Historical Park was dedicated in 1959. Even then, the area’s importance as a route through the mountains hadn’t changed. 50 years prior, the Bureau of Public Roads built a 2 and a half mile ribbon of crushed, compacted, and rolled limestone highway through Cumberland Mountain to link the towns of Middlesboro, Kentucky, and Cumberland Gap, Tennessee, and the wilderness road later disappeared under U.S. Highway 25E. As the highway became heavily trafficked, accidents became more and more frequent on the winding mountain road, earning it the nickname “Massacre Mountain.”

In an unlikely alliance, conservationists, historians, the park, and highway engineers joined forces to push for a major construction project that would reroute the highway through a tunnel beneath the historic Cumberland Gap.

In 1973, legislation was passed allowing the National Park Service to construct tunnels through Cumberland Mountain in order to remove traffic from the historic corridor and restore the image of the Gap and Wilderness Road.

The project cost $265 million and required rerouting two U.S. highways, the construction of twin 4,600-foot tunnels, five miles of new 4-lane approaches to the tunnels, two highway interchanges, and 10 bridges, including a 200-foot railroad bridge and two pedestrian bridges on hiking trails.

In 1985, Construction began on a pilot tunnel that was 10 feet wide and 10 feet high, drilled from both sides of the mountain. It took two years to drill, and revealed springs that produced 450 gallons of water every minute varying rock and clay, massive caverns, and a 30′ deep underground lake.

It took another 10 years to build the actual tunnels, which were are lined with a waterproof PVC membrane. A massive water management and drainage system was designed and installed, and water quality was constantly monitored during the construction process.

The tunnels opened to traffic in October 1996, and the section of U.S. Highway 25E was closed, and the asphalt removed. Now, there’s just a six-foot-wide trail—not too different from the one carved by Daniel Boone.18,000 vehicles passed through the park on an average day before the tunnels were built, now double the amount passes through the tunnels.

Today, you can discover the rich history of the area while experiencing the stunning nature, from spectacular overlooks to cascading waterfalls, along an extensive trail system that traverses Cumberland Gap National Historical Park’s 24,000 acres.

A guided tour takes visitors a mile down the Wilderness Road to the majestic Gap Cave. Another takes you to the historic Hensley Settlement, where the stories of early pioneers and settlers come alive in the numerous historic buildings and structures.

Wildlife is abundant in the park, including deer, beaver, fox, bobcat, bear, and over 150 species of birds. Rock formations abound and mountain streams flow over them to create beautiful waterfalls.

The 160-site Wilderness Road Campground is located 3 miles from the park visitor center off of Highway 58 in Virginia. Electrical hookups are available at 41 of the sites, and the campground provides hot showers and potable water. Campsites are available on a first-come, first-served basis. Backcountry camping is available in some of the more remote, wilderness areas.

This episode of America’s National Parks was written by me, Jason Epperson, and narrated by Abigail Trabue. If you enjoyed the show, we’d love a 5-star review wherever you listen to podcasts. Don’t forget to subscribe, and follow us on Facebook, Twitter, and Instagram. Just search “National Park Podcast.” You can also join our new America’s National Parks Facebook group. We’ll link to all of our social media, as well as National Park Service resources, music credits, and more in the show notes at National Park Podcast dot com.

If you are interested in RV travel, give us a listen over at the RV Miles Podcast. You can also follow Abigail and I as we travel the country in our converted school bus with our three boys at Our Wandering Family dot com.

Today’s show was sponsored by L.L.Bean, follow the hashtag #beanoutsider, and visit LLBean.com to find great gear for exploring the National Parks.


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