Legends of the Old West - FRONTIERSMEN Ep. 2 | Daniel Boone: “Battle For Boonesborough”

Episode Date: October 1, 2025

During the American Revolutionary War, Daniel Boone helps blaze a trail to Kentucky called the Wilderness Road. He establishes settlements and leads a daring rescue mission to recover three girls who are kidnapped by the Shawnee. Then, he defends his settlement of Boonesborough against waves of Shawnee attacks. Join Black Barrel+ for ad-free episodes and bingeable seasons: blackbarrel.supportingcast.fm/join Apple users join Black Barrel+ for ad-free episodes, bingeable seasons and bonus episodes. Click the Black Barrel+ banner on Apple to get started with a 3-day free trial. For more details, visit our website www.blackbarrelmedia.com and check out our social media pages. We’re @OldWestPodcast on Facebook, Instagram and Twitter. On YouTube, subscribe to LEGENDS+ for ad-free episodes and bingeable seasons: hit “Join” on the Legends YouTube homepage. Learn more about your ad choices. Visit megaphone.fm/adchoices

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Life's the trip. Make the most of it at Best Western. Book direct and save at bestwestern.com. 40-year-old Daniel Boone was no stranger to frontier violence. But in early 1774, reports swirled throughout the British colonies that startled even the most intrepid frontiersmen. Ambushes, massacres, and mutilations by Shawnee warriors and their allies occurred up and down the Appalachian mountain range. Boone was well aware of the tenacity of frontier warfare.

He was born into a Quaker family in Pennsylvania, but most of his life was spent traversing the forests of North Carolina and Virginia colonies. His passion for the woods earned him a reputation as a skilled marksman and ferocious hunter. Even when he married and started a family, Boone always itched for new adventures. During the French and Indian War, in which he served as a militiamen, Boone learned tales of an uncharted region called Kentucky, which was supposed to be a hunter's paradise.

For years, Boone dreamed of seeing Kentucky, and when he finally did, he had visions of leading settlers to create a new community. Unfortunately, events throughout the colonies constantly delayed his plans, which was what was happening again in 1774. Tensions between settlers and the indigenous people in the Ohio River Valley had simmered for years. The river itself would eventually help form the boundaries of five American states, and the River Valley as a whole was enormous. It encompassed half of Pennsylvania, most of Ohio and Indiana, parts of Illinois and Virginia,

and all of West Virginia and Kentucky. In Kentucky, Boone had already had dangerous and deadly dealings with the Shawnee. In 1767, during a long hunting expedition, he was captured and held captive by the Shawnee before he escaped to reunite with his group. Five years later, in 1773, while Boone led prospective settlers from North Carolina to Kentucky, his eldest son, James, died during a Shawnee attack. That attack essentially ended Boone's first attempt to establish a permanent settlement in Kentucky. He sent his family and many of the 50 potential settlers back home to North Carolina. Now, in early 1774, Boone heard of renewed troubles between colonists and Native Americans

in the borderlands between Ohio, Pennsylvania, and Virginia, at a time when the current states of West Virginia and Virginia were one big colony. In the area around what is now the panhandle of West Virginia, the narrow strip of land that is sandwiched between Ohio and Pennsylvania, the previously sporadic back-and-forth killings became more concentrated. In mid-April, groups of Cherokee stole horses and killed colonists in at least two separate attacks. In response, colonial men launched raids against any Native Americans they could find. On April 27th and 28th, The colonists attacked two separate groups of peaceful Native Americans, one of which had recently arrived at a fort to trade for goods.

On April 30th, many of the same colonial men assembled at a spot on Yellow Creek in what is now the northernmost tip of the West Virginia Panhandle. There are numerous versions of the story of the events that followed, but the most common is that the men gathered to defend the family of a man named Baker. Baker ran a tavern on Yellow Creek, and he had heard that a party of Mingo were coming to kill him and his family. The Mingo were sometimes identified as a singular tribe and sometimes as a collection of people who came from other tribes in the Iroquois Confederation. And the name Mingo is common in West Virginia today. That day in April 1774, the story says that a group of Mingo arrived at Baker's Tavern and started

drinking heavily, without knowing that more than 20 colonial men were hiding in a back room. The colonial men attacked the mingo and killed nearly all in the group. Then the attackers rushed outside and saw more mingo crossing Yellow Creek in two canoes. The attackers shot and killed most of the mingo in the first canoe, which caused the people in the second canoe to frantically turn around and paddle back across the creek. There's no reliable, figure for the number of dead, but it was likely in the double digits. And in the most gory versions of the story, at least one of the colonial men subjected some of the Native American victims to gruesome and horrifying mutilations. Regardless of the details, the attack

became known as the Yellow Creek Massacre. When word spread, the Mingo and their formidable allies, the Shawnee, responded by attacking colonial settlers. Before long, the conflict known as Lord Dunmore's war was underway, and Daniel Boone would once again answer the call to arms. I'm your host, Chris Wimmer, and this season we're telling the stories of two of America's most famous frontiersmen, Daniel Boone and Davy Crockett. This is episode 2, Daniel Boone Part 2, Battle for Boonesboro. In the days following the Yellow Creek Massacre, the Mingo and their Shawnee allies were hell-bent on vengeance, and they began attacking settlers with impunity. The violence got so bad that the Virginia House of Burgesses declared war on the Shon.

and the Mingo. The conflict was called Lord Dunmore's War, named after Lord Dunmore, John Murray, the governor of Virginia, and it had wider implications than back and forth reprisals by both sides. For Governor Dunmore, the war was a chance to finally establish a firm and protected border for his colony. For many settlers, the war was an opportunity to acquire more land. And for some, the war gave settlers a reason to avenge those who died at the hands of the Shawnee. In the opening stages of the war, Governor Dunmore knew that there were numerous land surveyors along the Virginia-Kentucky border who were examining land for future settlements. Realizing the men had no clue that war had broken out, Dunmore called on his militia leaders

to find two of the best woodsmen who could quickly venture out and warn the surveyors. The leaders put forth Daniel Boone's name right away. The second woodsman was a German-American hunter named Michael Stoner. The militia leaders found Boone in western Virginia while he was on a trip to visit the grave of his son James. Boone and Stoner set out on June 26th. As they began their journey, they realized that most of the surveyors had moved deep in eastern Kentucky. Instead of being on the Virginia border, the men were in the heart of Shawnee territory. For 61 grueling days, Boone and Stoner traversed more than 800 miles. They managed

to find multiple surveyor parties, and they relayed the news about the war. But the woodsmen also discovered the dead and mutilated bodies of surveyors who had been unlucky to run into the Shawnee. Boone and Stoner instructed the lucky ones to return to Virginia as quickly as possible. Finally, in August, the two woodsmen headed home. By some miracle, they themselves did not come into conflict with the Shawnee. And when they returned to Virginia, they were heralded as heroes. And after reporting to his superiors, Daniel Boone became a lieutenant in the militia and was given command of Fort Blackmore and Fort Cowan, located in Southern Virginia near the North Carolina border. In the months that followed, Boone and his militiamen kept Shawnee

incursions at bay. Brief but ferocious attacks took place, and the militia repulsed the warriors. Unfortunately, few details of the skirmishes survive, but for his leadership in combat, Boone was promoted to captain. He had learned how to defend important strategic locations without any formal military training. It quickly became obvious that Daniel Boone was a natural leader. While Boone kept Fort Blackmore and Fort Cowan on alert, the Virginia militia scored a major victory at the Battle of Point Pleasant, located in modern-day West Virginia on October 10, 1774. While the first Continental Congress met in Philadelphia to discuss the future of the American colonies, 375 miles to the west, the militiamen forced the Shawnee to concede that continuing the war was pointless.

While some allied tribes refused to negotiate, Chief Cornstalk of the Shawnee, as he was known to white settlers, agreed to terms with Virginia. The Shawnee gave up some land in Kentucky and agreed to stop harassing settlers. Lord Dunmore's war was officially over, and Daniel Boone believed he had a new opportunity to settle Kentucky. At the start of 1775, he began recruiting settlers who were willing to take the risk. Okay, flights on Air Canada.

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Daniel Boone believed his new venture would be different from his first journey two years earlier. This time, he thought the Shawnee were committed to peace. Thanks to Chief Cornstalk, there was now an agreement between colonists and at least some of the Shawnee. While still a dangerous expedition, Boone assumed the territory was no longer hostile. In addition, Boone had a wealthy sponsor. Richard Henderson was a prosperous former judge in North Carolina, and he wanted to help establish a colony in eastern Kentucky called Transylvania. Henderson and Boone met with Cherokee leaders to purchase 20 million acres of land

that overlapped with Shawnee claims. Before Boone dared to bring any women and children to Kentucky, he decided to clear a road through the Cumberland gap to make it easy for future pioneers. On the morning of March 10, 1775, Boone and more than 30 men shouldered axes and began cutting a trail through the hilly terrain. Unfortunately, the promised peace between settlers and the Shawnee didn't hold. And as the so-called Wilderness Road crossed into Kentucky, Boone's company was ambushed by Shawnee Warriors. During the melee, two of Boone's company, an enslaved man named Sam, and Sam's owner,

were killed before the rest of the company were able to drive their attackers off. When the fight was done, Boone gave both dead men proper burials. Mercifully for the company, the attack was an isolated incident. After three grueling weeks of work, Boone's company completed the wilderness' road into eastern Kentucky along the Kentucky River. The Wilderness Road, or Boone's Trace as it was also known, became the first major route for Americans to venture westward into Kentucky. In April, Boone established a fort to serve as the first attempt to create a permanent settlement.

Unsurprisingly, the stockade was named after the man who was responsible for blazing the trail. The fort and the subsequent town constructed at the site was called Boonesboro. Today, it's a small community about 15 miles southeast of Lexington. In 1775, it was a compound which featured a giant rectangular perimeter fence with four blockhouses guarding the corners. When Boonesboro was finished, Boone sent for his family to join him in Kentucky. By the time Rebecca Boone arrived with their seven children in May 1775, Boonesboro had been joined by two neighboring settlements,

Logan's Station, and Herodzburg. Together, the settlements became a triumvirate of fortified locations to welcome settlers. Now that Boone was settled with his family, he was starting to see his dream in Kentucky realized. And while Daniel Boone was, at last, enjoying the fruits of his labor in Kentucky, much was changing in the North American colonies. Many of his fellow settlers in the colonies were exasperated with the British government over laws, taxes, and perceived mistreatment. In the years after the French and Indian War, colonists had increasingly become tired of being treated like second-class citizens. During the years, while Boone was fixated on settling Kentucky, there was growing sentiment throughout the colonies toward the prospect of seeking independence. In the spring of 1775, around the time Boonesboro was established,

the simmering tension between the colonists and the crown boiled over. The first shots of war were fired at Lexington and Concord on April 19th. Two months later, colonial troops fought valiantly at Bunker Hill. As American militiamen clashed with British soldiers, several Native American nations on the frontier saw the brewing war as an opportunity. If they threw in their lot with the British, they could reclaim lands surrendered in treaties with colonial governors. Two of the nations looking to reclaim their lost land were the Shawnee and the Cherokee, and they had their sights set on Kentucky. The Shawnee and Cherokee sought to stamp out any and all incursions into their territory by colonial settlers.

settlers. When war broke out between the British and the American colonists, the Shawnee and Cherokee allied with the British. Soon, warriors from both tribes began to attack American settlers whenever they could. The biggest challenge was Boonesboro. Daniel Boone's longtime dream of a settled Kentucky, and the immediate urgency of the safety of his family were under threat. Over the course of a year of sporadic fighting from the spring of 1775 to the spring of 1776, Boone became increasingly worried. The settlers hunkered down in the fortified compound of Boonesboro, but as Daniel Boone would painfully experience, kids will be kids. They don't always listen to their parents, even in times of danger and crisis. On July 14, 1776, Boone's 13-year-old daughter,

Jemima and two friends, Elizabeth and Francis Calloway, decided to take a canoe out onto the Kentucky River. As the girls paddled away from Boonesboro, they were unaware they were being watched. Hidden in the trees, five warriors, three Shawnee and two Cherokee, spied the canoe. When the canoe neared the riverbank, one of the warriors jumped out of the brush and grabbed the boat. The girls started to scream, but one of the warriors grabbed a girl and made a gesture of scalping, which silenced all of them. Jemima told a warrior that she was Daniel Boone's daughter, and claimed that the Callaway sisters were also Boone's children. Jemima assumed that if the warrior knew she was related to Boone, it might save them from mistreatment. The warrior believed Jemima, but that did nothing to stop the abduction.

With their captives in tow, the warriors dragged the girls into the woods. As fate would have it, the girls' screams had reverberated across the creek and reached the ears of a few Boonesboro residents who were working outside of the settlement's walls. Realizing people were in danger, nine men grabbed their rifles, mounted horses, and rode off to investigate. Daniel Boone decided he should go too, having no idea his daughter had been taken. Boone led a small party across a nearby stream, and they instantly saw the abandoned canoe and signs of the abduction. Boone and his men raced into the woods and easily picked up the warrior's trail.

Part of it was Boone's experience as an expert woodsman and tracker, but the girls also helped. The warriors had horses, but they forced the girls to walk, so the girls dragged their feet to leave marks on the ground. They snapped branches. and dropped small bits of cloth from their clothes. Jemima Boone made life especially difficult for the warriors. Like the Callaway sisters, when the warriors made Jemima walk, she dragged her feet.

When they put her on a horse, she harassed the animal to the point that it refused to carry her. Boone's search party followed the trail throughout the night. At dawn the next day, Boone made a calculated decision. He feared that if they all followed the trail, the warriors might hear them approach. If the warriors saw the settlers coming, they might kill the captives immediately. Boone proposed they abandoned the trail and head to a nearby river crossing which he believed the warriors planned to use. It was a risk to leave the trail, but it was a risk worth taking if it meant saving the girls. As night fell on the third day of pursuit, Daniel Boone and

his company approached the river crossing and he discovered his prediction was right. Near the Eight people huddled around an open flame as meat from a dead buffalo calf cooked over the fire. Boone and his men could see the five warriors and the three young girls. As quietly as possible, Boone's group circled around the camp and waited to strike. Through the leaves, Boone saw and heard the Callaway girls crying. turned and saw one of the warriors standing right beside the fire. After surveying the scene, Boone realized the warrior by the fire would be the easiest target. Boone leveled his rifle, and the other men with him did the same. Francis Calloway was kneeling near her sister when she looked

up at the warrior standing by the fire. As she did, she heard a loud bang and saw blood spurt from the warrior's chest. Boone's opening shot had hit its mark. Jamima shouted, quote, That's Daddy, and the rest of Boone's company opened fire. Jemima and Francis dropped down to avoid the musket balls which tore through the camp. Elizabeth Calloway didn't hit the ground, most likely because she was in shock. One of the warriors swung a club at her head. One of the rescuers, Daniel Boone, according to his autobiography, fired a shot before the Warriors' club hit its mark.

The warrior fell, and Boone and his men burst out of the trees. The frontiersmen blitzed the camp from multiple angles. Taken aback, the three surviving warriors ran away and left behind almost everything they had. In the confusion, gun smoke, and dim lighting, one of the rescuers nearly shot Elizabeth Calloway. She rushed toward one of the men, and all he could see was a dark shape hurrying toward him. The man aimed his weapon at Elizabeth, but Boone shouted, quote, for God's sake, don't kill her when we've traveled so far to save her. With the girls now safe, the party returned to Boonesboro.

When they got back, Boone learned that another band of warriors had burned outlying cabins and crops. Thankfully, no one had died. But the people of Boonesboro and the neighboring communities would need to be extra vigilant because there seemed to be no sign that the fighting would end anytime soon. As war began to grip the colonies in the north and slowly extended south, the story of Daniel Boone's rescue mission to save the three girls grew into legend.

Fifty years later, it inspired author James Fenimore Cooper's famous novel, The Last of the Mohicans. At one point in the story, the daughters of a British officer were kidnapped by a Huron war chief, and the protagonist, a frontiersman, set out to rescue them. 166 years after the novel was published, that sequence of a frontiersman leading a small group to rescue an officer's daughter became one of the greatest sequences in cinematic history in the 1992 film adaptation of The Last of the Mohicans, starring Daniel Day Lewis.

In July of 1776, Daniel Boone's leadership inspired confidence in those around Boonesboro. His bravery was infectious, which was important because the war for American independence was about to expand beyond the epicenter of Boston and New York. While British forces planned to press General George Washington in New York, they were debating how to handle colonists on the frontier. Lieutenant Governor Henry Hamilton, the British Superintendent of Indian Affairs stationed at Fort Detroit in modern-day Michigan,

was responsible for crafting frontier war policy. Initially, Hamilton was encouraged to keep Native American tribes neutral, but as the war progressed, the policy changed. Instead of keeping Native American nations away from the war, Hamilton received orders to make them a central part of it. The objective was to convince tribes that the best way to retain their territory was to defeat the American rebels. The Shawnee and Cherokee were two nations of many who supported the British, while others, like Boone's friends in the Kataba Nation, mostly sided with the American colonists.

After the British instituted a new policy of enlisting help from Native American nations, there followed a period on the frontier called the Bloody Sevens, named after the year the raids began 1777. Henry Hamilton sanctioned Shawnee and Cherokee raids across the frontier. Hundreds of men, women, and children on the western boundaries of Pennsylvania, Virginia, and North Carolina were killed and scalped. One of the colonial leaders on the frontier in Kentucky wrote to the governor of Virginia in February 1777 and told him, quote, We are surrounded with enemies on every side, and our fort is filled with widows and orphans. At the same time, Hamilton's biggest fear with the plan came true.

Warriors also attacked colonists who were loyal to Britain. Whether on purpose or because it was likely hard for warriors to tell the difference between colonists who were loyal to Britain and those who were loyal to the new American nation, the raids which killed loyalists ended up pushing other loyalists to switch sides. But even though sentiment on the colonial frontier was slowly shifting in favor of the American colonists, that didn't mean settlements like Boonesboro were safe. In fact, Daniel Boone knew it wasn't, at least in terms of a large-scale attack. If a large force of Shawnee concentrated an attack on Boone'sboro,

Boone feared the settlement would fall. Major George Rogers Clark, an American officer in the Virginia militia, realized the importance of Boone's Kentucky settlements. Clark successfully navigated Boone's Wilderness Road in order to help resupply Kentucky outposts with gunpowder and to recruit men to fight. When Clark arrived, he conferred with Boone. Boone was ready and willing to help defend Kentucky

and Clark made Boone a militia captain. To Boone's dismay, he and the militia were never on the offensive. They defended settlements, which meant they were forced to deal with ambushes. On March 5th, 1777, Shawnee leader, Chief Blackfish, and 70 warriors attacked settlers who were crafting maple syrup. The Shawnee mutilated their bodies and drank the syrup before racing away through the woods. On April 24th, a larger attack erupted. The day started with two men leaving Boonesboro to drive some horses which were grazing near the fort.

Before rounding up the horses, the two men were shot by Sean. Shawnee Warriors. One of the two was overtaken and scalped. A nearby settler, Simon Kenton, just so happened to be hunting in the area. Kenton saw the Shawnee attack and hurled himself into the fray. He shot the warrior who was hoisting the scalp. Inside Boonesboro, Daniel Boone heard the shots. Expecting a small ambush, Boone gathered some men and raced outside the fort to investigate, which was when Boone realized they had fallen into a trap. More than 100 Shawnee warriors emerged from the woods around the compound, including Boone and Simon Kenton, who had just killed a Shawnee warrior, the settlers numbered 14 men who now faced more than a hundred warriors. Almost immediately, both sides began to fire. In roughly a minute, Simon Kenton had killed a pair of warriors, but the two kills and the shots from other frontiersmen did little to hold back the flood as the bulk of the Shawnee Warriors rushed toward the fort's entrance. The warriors blocked the only route for Boone and his men

to make it back inside, but the warriors did not try to enter the compound. They were intent on destroying the defenders first, then they could raid the helpless community. As Boone reloaded his long rifle, he said to the other men, quote, boys, we are gone, but let us sell our lives as dearly as we can. If the defenders couldn't survive the fight, they would take as many Shawnee warriors with them as possible. The frontiersmen charged the Shawnee, and the real battle for Boonesboro began. Daniel Boone and the other 13 defenders of Boonesboro fired a volley from their muskets as they ran toward the Shawnee Warriors who blocked the entrance to the compound.

When the rifles were empty, the defenders raised the weapons to use as clubs. Both sides screamed as they engaged. in brutal hand-to-hand combat. The gates of Boonesboro were a swarm of sickening thuds, anguished cries, and sprays of blood. Early in the battle, Boone felt a horrific pain in his lower leg. He looked down and saw blood pouring from his ankle. He had been shot, and the round broke the bone. Boone crashed to the ground, and as he looked up, he saw a Shawnee warrior rush toward him with a tomahawk. Boone braced for the blow, which would crush his head. but it never came.

Before the warrior reached Boone, the warrior's chest exploded. Boone looked around and saw smoke billowing from Simon Kenton's rifle. When a second Shawnee warrior raced toward Boone, Kenton swung his rifle and clubbed the man. That made at least four warriors Simon Kenton had killed during the day's work.

He was a one-man wrecking crew, and now he was a one-man rescue party. Kenton grabbed Boone and used every ounce of his strength, to hoist the injured man. Kenton carried Boone into the fort, where Rebecca Boone and her daughters rushed to Boone's aid. Outside Boone's walls, the battles still raged, but not for long. Three more defenders were wounded, but none were killed. Miraculously, the 14 frontiersmen managed to survive and retreat into the fort. The Shawnee lost 22 men in the fort. The Shawnee lost 22 men in the fight. They never breached the gates, and then they faded back into the forest where they decided

the price for admittance was too high. In the days that followed, Boone powered through his broken leg. Although he needed to rest, he refused to stay in bed. He hobbled around Boonesboro to prepare the fort for future attacks. He also helped establish an intelligence network between the scattered settlements in Kentucky. From Boonesboro to Herodzburg, Boone sent scouts scouts to spy on Shawnee movements in a 50-mile radius. The situation was precarious. None of the settlements could spare men to assist the others, and each settlement essentially became imprisoned in its own stockade.

In late May 1777, as General George Washington and the Continental Army prepared to break their winter camp at Morristown, New Jersey, Daniel Boone organized the men of Boonesboro into two groups. One would tend crops and the other would guard the workers. Boone instructed the guards to watch for the glint of sunlight off of gun barrels. That would be the telltale sign of Shawnee attackers lurking in the trees. Boone didn't want the men to fire at every twitch of a bush or snap of a twig. The Shawnee were too smooth to give themselves away by moving recklessly,

and the wasted ammunition could be a costly mistake. But that didn't mean the Shawnee weren't out there. They were, and everyone knew it. It was only a matter of time before they massed for another attack. And if roughly 100 warriors couldn't get the job done the first time, they would surely bring more the second time. On May 23, 1777, that was exactly what happened. More than 200 Shawnee warriors crept through the brush toward the compound,

and the people of Boonesboro were about to find themselves under siege. Next time on Legends of the Old West, somehow Daniel Boone's life becomes even more crazy. He helps defend Boonesboro against numerous attacks. He gets captured and nearly killed by the Shawnee. He faces a shocking court-martial for treason. And, as a frontiersman to the end, he continues his adventures to the expanding western frontier

of the new American nation. That's next week on the end of the Daniel Boone story here on Legends of the Old West. Members of our Black Barrel Plus program receive each new season to binge all at once with no commercials, as well as exclusive bonus episodes. Sign up now through the link in the show notes or on our website Blackbarrelmedia.com. or subscribe directly on Apple Podcasts through the podcast show page. This series was written and researched by Michael Meglish. It was produced by Joe Garrow, original music by Rob Valier. I'm Chris Wimmer. Thanks for listening.