Simon Kenton

April 3, 1755–April 29, 1836

Simon Kenton was a Frontiersman, scout, and soldier who is most famous for helping defend Kentucky settlers from the late Colonial Era to the Early Republic. Kenton is one of the most important figures of the early era of Westward Expansion and Manifest Destiny and was associated with Daniel Boone and George Rogers Clark.

Simon Kenton, Illustration, Dodson

Simon Kenton by Richard W. Dodson, circa 1834–1839. Image Source: Pennsylvania Academy of the Fine Arts.

Simon Kenton Facts

  • Born — Simon Kenton was born on April 3, 1755.
  • Place of Birth — Kenton was born in Fauquier County, Province of Virginia.
  • Parents — Mark Kenton and Mary Miller.
  • Married — Kenton married Martha Dowden in 1787. He married Elizabeth Jarboe in 1796.
  • Children — He had four children with Dowden and five with Jarboe.
  • Death — Kenton died on April 29, 1836, at his cabin near Zanesfield, Ohio.
  • Fun Fact — He is believed to have survived the Native American Indian ritual known as “Running the Gauntlet” 10-13 times.
  • Fun Fact — Known as a fierce Indian Fighter, there was mutual respect between Kenton and the Indians, including prominent leaders like Chief Logan and Tecumseh.
  • Nickname — The Shawnee called him “Cut-ta-ho-tha” meaning “The Condemned Man.”

Simon Kenton Significance

Simon Kenton is important to American History because of his contributions to the settlement and defense of Kentucky, which joined the Union on June 1, 1792, as the 15th State. Widely known as a fierce Indian Fighter, Kenton was known to be an exceptional Frontiersman, scout, and hunter. As a soldier and scout, he fought in the American Revolutionary War (1775–1783), the Northwest Indian War (1785–1795), and the War of 1812 (1812–1815). In his later years, he was often troubled by financial and legal issues. Although he is overshadowed by prominent figures like Daniel Boone (1734–1820) and George Rogers Clark (1752–1818), Kenton’s accomplishments were significant to the early years of Manifest Destiny and Westward Expansion.

Simon Kenton History

Life and Career of the Famous Frontiersman

Simon Kenton was born on April 3, 1755, in Fauquier County, Virginia to Mark Kenton and Mary Miller. Although he had the opportunity to attend school and earn an education, he refused to attend and never learned to read or write — other than writing his signature. He spent his time working on a tobacco farm and exploring the wilderness.

Fight with William Leachman

In 1770, when Simon Kenton was about 16, he was involved in a fight with William Leachman over a girl. Kenton was upset that Leachman asked the girl to marry him and that she agreed. Kenton challenged Leachman to a fight but was soundly beaten. A few months later, Kenton reissued the challenge. This time, he knocked Leachman out. Fearing he had killed him, Kenton ran away. He went west, and took nothing with him, other than the clothes he was wearing. He constantly changed his last name to maintain his anonymity.

Simon Kenton, Fight with Leachman, Illustration
This illustration depicts Kenton’s fight with Leachman. Image Source: Harper’s Monthly, February 1864.

“At the age of sixteen, by an unfortunate adventure, he was launched into life, with no other fortune than a stout heart and a robust set of limbs. It seems that, young as he was, his heart had become entangled in the snares of a young coquette in the neighborhood, who was grievously perplexed by the necessity of choosing one husband out of many lovers. Young Kenton and a robust farmer by the name of Leachman seem to have been the most favored suitors, and the young lady, not being able to decide on their respective merits, they took the matter into their own hands, and in consequence of foul play on the part of Leachman’s friends, young Kenton was beaten with great severity.

He submitted to his fate, for a time, in silence, but internally vowed that as soon as he had obtained his full growth, he would take ample vengeance upon his rival, for the disgrace which he had sustained at his hands. 

He waited patiently until the following spring, when, finding himself six feet high, and full of health and action, he determined to delay the hour of retribution no longer. He, accordingly walked over to Leachman’s house one morning, and, finding him busily engaged in carrying shingles from the woods to his own house, he stopped him and told him his object, and desired him to adjourn to a spot more convenient for the purpose. 

Leachman, confident in his superior age and strength, was not backward in testifying his willingness to indulge him in so amiable a pastime, and having reached a solitary spot in the wood they both stripped and prepared for the encounter. 

The battle was fought with all the fury which natural hate, jealousy, and herculean power on both sides could supply; and after a severe round in which considerable damage was done and received, Kenton was brought to the ground. Leachman (as usual in Virginia) sprung upon him without the least scruple, and added the most bitter taunts to the kicks with which he saluted him from his head to his heels, reminding him of his former defeat, and rubbing salt into the raw wounds of jealousy by triumphant allusions to his own superiority both in love and war. During these active operations on the part of Leachman, Kenton lay perfectly still, eying attentively a small bush which grew near them. It instantly occurred to him, that if he could wind Leitchman’s hair, (which was remarkably long,) around this bush, he would be able to return the kicks which were now bestowed upon him in such profusion. The difficulty was to get his antagonist near enough. This he at length effected in the good old Virginia style, viz.: by biting him en arriere, and compelling him by short springs to approach the bush, much as a bullock is goaded on to approach the fatal ring, where all his struggles are useless. When near enough Kenton suddenly exerted himself violently, and succeeded in wrapping the long hair of his rival around the sapling. He then sprang to his feet and inflicted a terrible revenge for all his past injuries. In a few minutes Leachman was gasping, apparently in the agonies of death. Kenton instantly fled, without returning for an additional supply of clothing, and directed his steps westward

This was on April 6, 1771. During the first day of his journey he traveled in much agitation. He supposed that Leachman was dead, and that the hue and cry would instantly be raised after himself as the murderer. The constant apprehension of the gallows lent wings to his flight, and he scarcely allowed himself a moment for refreshment, until he had reached the neighborhood of Warm Springs, where the settlements were thin and the immediate danger of pursuit was over.”

AHC Note — This description of Kenton’s fight with Leachman comes from an article written by R.W. McFarland and published in 1904.

Journey to Fort Pitt

Kenton worked his way across Virginia and Pennsylvania, trading work for lodging and food. Along the way, he met several people who were traveling west. There was a man named Johnson, who was from the New Jersey Colony. Then there was a small expedition led by John Mahon and Jacob Greathouse. In traveling with these people, Kenton was exposed to the wonders and hardships of life on the frontier.

Simon Butler

Kenton traveled with the expedition to the area around Fort Pitt, at present-day Pittsburgh, where he met two frontiersmen. By then, Kenton was calling himself “Simon Butler,” which he continued to use for many years.

The men were planning to follow the Ohio River into the place called Kentucky, in search of the legendary “Canelands,” which were said to be fertile and full of game. One of the men was Jacob Yaeger, who was known as the “Long Dutchman.” Yaeger had been to Kentucky as a child, after being taken captive by Native American Indians. The other man’s name is only known as “Strader.” They invited Kenton to join them, and he agreed. 

Yeager led the way, believing he would remember the route and landmarks from his childhood. They floated down the Ohio River in a canoe to present-day Maysville, Kentucky, about 60 miles southeast of present-day Cincinnati, Ohio, and 60 miles northeast of present-day Lexington, Kentucky. 

However, Yeager failed to find the landmarks he was looking for, so they turned back. They explored some rivers, including the Great Kanawha River, and made their way to present-day Charleston, West Virginia. They decided it was a good place to camp and hunt, and spent the remainder of 1771 collecting animal pelts. In early 1772, they took the pelts to Fort Pitt and traded them for supplies and ammunition.

Afterward, they returned to their hunting grounds in West Virginia. In March 1773, they were attacked by Indians. Yeager was killed, but Kenton and Strader escaped into the forest, wearing only their shirts. They were saved by settlers living in a cabin, who provided them with food and clothing while they recovered from the incident.

After he recovered, Kenton was determined to make his way to Kentucky. He found a way to secure a rifle and ammunition and continued to hunt through 1773, in the area around the Little Kanawha River in West Virginia. 

Ohio Company

In early 1774, Kenton joined an expedition funded by the Ohio Company of Associates that was surveying the territory. The expedition was led by Hancock Lee who was supposed to join another expedition, led by Captain Thomas Bullitt. Lee’s expedition was attacked by Indians and forced to return to the safety of the settlements in West Virginia. Kenton resumed hunting along the Little Kanawha.

Lord Dunmore’s War

In the spring of 1774, Lord Dunmore’s War started, and Kenton served as a scout for John Murray, who was Lord Dunmore and the Governor of Virginia. 

The war was started by an incident known as the “Yellow Creek Massacre.” On April 30, 1774, a group of Americans led by Daniel Greathouse and Jacob Greathouse attacked a Mingo village and killed the family of Chief Logan, who had been an ally up to that point. Logan responded by declaring war on the settlers.

Kenton traveled to Fort Pitt to volunteer for Lord Dunmore’s army. There, he swore an oath of allegiance to King George III and was introduced to George Rogers Clark and Simon Girty.

John Murray, Earl of Dunmore
John Murray, Lord Dunmore. Image Source: Google Arts & Culture.

“…when war broke out with the Indians, chiefly on account of the murder of Logan’s relations by some evil-disposed white men. Lord Dunmore, Governor of Virginia, raised two large bodies of troops, with a view of conquering a peace. 

One division was commanded by Colonel Andrew Lewis, and marched from the central parts of Virginia to the mouth of the Great Kanawha, where the celebrated battle of Point Pleasant was fought on October 10, 1774. 

Lord Dunmore’s division went down the river from Pittsburg to the mouth of the Hocking, built a fort, and then advanced towards the Pickaway plains on the Scioto. Kenton and Simon Girty were two of Dunmore’s scouts, and their weeks of service together laid a foundation for friendship which on a later occasion resulted in rescuing Kenton from the stake. These men carried dispatches from Dunmore to Lewis before the battle, but neither of the scouts was in the fight, having set out on the return journey.

In the year 1775 Girty left the whites and took up his abode with the Indians, and became one of them. Two or three of Girty’s brothers had been captured in boyhood and were living with different tribes. Shortly after the battle of Point Pleasant, the remainder of Lewis’s forces joined Dunmore on the Scioto, and a treaty was made with the Shawnees, after which the troops returned to Virginia.”

AHC Note — This description of Lord Dunmore’s War is from R.W. McFarland’s 1904 article.


At the beginning of Lord Dunmore’s War, Kenton and Jacob Drennan were assigned to the command of Colonel Angus McDonald, serving as scouts. 

It was their job to guide McDonald and his men to Indian villages along the Muskingum River in present-day Ohio, including the Shawnee village of Wapatomica. The journey covered 400 miles on water and then a 90-mile march through the wilderness.

Near Wapatomica, the Shawnee ambushed them and then tried to set up peace negotiations. However, the scouts discovered the meeting was another trap and warned McDonald. The Virginia forces used it to their advantage. They surprised the Shawnee, routed them, and then destroyed Wapatomica and four more Indian villages along the river.

Battle of Point Pleasant

Afterward, Lord Dunmore planned to attack the Shawnee villages along the Scioto River in Ohio, however, he needed to combine with Colonel Andrew Lewis and his command to have enough men for the expedition. Dunmore wrote his orders and gave them to Kenton and two other men to deliver to Lewis. 

During the journey to find Lewis, the three messengers were attacked by Indians, but survived. Kenton was the only one who continued the mission to reach Lewis. The other two abandoned him.

On October 10, 1774, Indian forces led by Chief Cornstalk of the Shawnee attacked Colonel Lewis and his command at Point Pleasant, in present-day West Virginia. It was a long, brutal battle, and the Americans won.

Lewis went on to attack and destroy more Shawnee villages in the area, forcing their leaders to negotiate with Dunmore. The war ended with the Indians agreeing to cede land south and east of the Ohio River to Dunmore, and promising not to harass Americans traveling on the river.

Logan’s Lament

Chief Logan refused to attend the negotiations with Lord Dunmore. Instead, he dictated a message to Simon Kenton, Simon Girty, and John Gibson, who was Logan’s brother-in-law. The message was written down by Gibson and the three of them delivered it to the negotiations. 

Known as Logan’s Lament, the message said:

“I appeal to any white man to say, if ever he entered Logan’s cabin hungry, and he gave him not meat; if ever he came cold and naked, and he clothed him not. During the course of the last long and bloody war, Logan remained idle in his cabin, an advocate for peace. Such was my love for the whites, that my countrymen pointed as they passed, and said, Logan is the friend of the white men. I have even thought to live with you but for the injuries of one man. Colonel Cresap, the last spring, in cold blood, and unprovoked, murdered all the relations of Logan, not sparing even my women and children. There runs not a drop of my blood in the veins of any living creature. This has called on me for revenge. I have sought it; I have killed many; I have fully glutted my vengeance. For my country, I rejoice at the beams of peace. But do not harbor a thought that mine is the joy of fear. Logan never felt fear. He will not turn on his heel to save his life. — Who is there to mourn for Logan? Not one.”

Yellow Creek Massacre, Historical Marker
This historical marker identifies the location of the “Yellow Creek Massacre,” also known as the “Logan Massacre.” Image Source: Waymarking.

The Canelands and Kenton’s Station

When the war ended, Kenton was only 19 years old and still dreaming of finding his way to Kentucky. In the spring of 1775, he traveled by canoe and made his way back to Maysville, at Limestone Creek, accompanied by Thomas Williams. According to R.W. McFarland, they left the river and moved deeper into the thick wilderness:

“A few miles back from the river they were greatly pleased with the beauty of the land, and the evidences of great fertility of the soil. At length, they fell in with a great buffalo trace which in a few hours brought them to the Lower Blue Lick. 

The flats on both sides of the river being crowded with great herds of buffalo, which had come to the salt licks; a number of deer appeared on the ridges near by, and the great object of their search was attained. 

And so pleased were they that the exploration was continued towards the south, until they had traversed, in great part, the land now constituting the counties of Scott, Woodford, Fayette, Montgomery, and one or two others. 

Finding another buffalo trace they followed it to the Upper Blue Lick, on their return route. This expedition had brought to their view a country superior to any that Yeager had led them to expect, and they determined at once to establish more permanent quarters. In all this long tramp they did not find any indications of white men.”

It was here they found the canebrake and the place came to be known as “Kenton’s Station.”

First Crop of Corn

Kenton and his Williams cleared about an acre of canebrake near Maysville, built a cabin, and planted a field of corn. It is believed this was the first crop of corn raised in the area. Kenton’s descendant, Edna Kenton, said Kenton “raised the first crop of corn ever cultivated by white men north of the Kentucky River.” Today, Kenton’s farm is located in present-day Mason County, Kentucky.

Transylvania Colony

By this time, more Americans were planning to establish a presence on the frontier. Judge Richard Henderson of North Carolina and Daniel Boone worked out the Treaty of Sycamore Shoals with the Cherokee Tribe. Henderson bought approximately 20 million acres of land from the Cherokee for £10,000 in silver. Today, Henderson’s purchase makes up most of present-day Kentucky, along with portions of Tennessee and West Virginia. Henderson intended to use the land for a new colony, called Transylvania.

AHC Note — Some accounts indicate Henderson traded goods, not silver, in exchange for the land.

Boone and the Wilderness Road

Although Henderson’s plan ultimately failed, Boone and a group of about 30 men blazed a road from Virginia into the heart of Kentucky. This path became known as the Wilderness Road. At the end of the road, Boone and his men established a settlement called Boonesborough, which was about 20 miles southeast of present-day Lexington, Kentucky.

Trouble with Indians Begins Again

Later in 1775, Kenton and Williams were exploring when they came across two men named “Fitzpatrick” and “Hendricks” who were lost. Kenton told them about his settlement and invited them to return with him. Hendricks agreed, but Fitzpatrick wanted to make his way to Pittsburgh. 

They left Hendricks near where they had found him and took Fitzpatrick to the river. When they returned to the campsite, they found Hendricks had been attacked and killed by Indians. With this, Kenton and Williams realized they were in more danger than they had believed. However, they remained at the settlement and were not harassed by the Indians. 

In September, an American happened to find them and told them about Boonesborough and other settlements, which were known as “stations.” Kenton and Williams visited the stations, which were typically small homes built inside of a larger fort, with fields outside the walls. Alongside Boonesborough, some of the prominent settlements were:

  • Harrod’s Town (or Harrodsburg)
  • Hinkston’s Station
  • Huston’s Station
  • Lexington Station
  • Logan’s Station
  • McClellan’s Station

While the American Revolutionary War was escalating on the East Coast, Indians resumed their attacks on American settlements on the frontier. Dragging Canoe, a Chickamauga chief, created an alliance between the Cherokee and various Shawnee tribes and carried out raids on American settlements, including the Siege of Fort Watauga (July 1776). 

By this time, Kenton was spending more time at Boonesborough, where he developed close ties with men like Daniel Boone and Robert Patterson.

Boonesborough was attacked at least three times and Major George Rogers Clark hired six men to serve as scouts. These men were tasked with keeping track of Indian movements and warning the settlements of pending attacks. Daniel Boone appointed Kenton and Thomas Brooks to keep watch over Boonesborough.

Rescue of Daniel Boone

In the spring of 1777, Chief Black Fish led Shawnee forces in an attack on Boonesborough. They laid siege to the fort for roughly a month. During the siege, Kenton was often sent out to hunt for food, but one day he also saved Daniel Boone’s life.

Simon Kenton, Saving Daniel Boone, Illustration
This illustration depicts Kenton saving Daniel Boone. Image Source: Harper’s Monthly, February 1864.

R.W. McFarland describes the incident:

“On one occasion, Kenton and two others early in the morning, having loaded their guns for a hunt, were standing in the gate of Boonesborough, when two men in the fields were fired on by the Indians. 

They immediately fled, not being hurt. The Indians pursued them, and a warrior overtook and tomahawked one of the men within seventy yards of the fort, and proceeded leisurely to scalp him. Kenton shot the daring savage dead, and immediately, with his hunting companions, gave chase to the others. 

Boone, hearing the noise, with ten men hastened out to the assistance of the spies. Kenton turned and observed an Indian taking aim at the party of Boone; quick as thought he brought his rifle to his shoulder, pulled the trigger first, and the red man bit the dust. 

Boone having advanced some distance, now discovered that his small party, consisting of fourteen men, were cut off from the fort by a large body of the foe, which had got between him and the gate.

There was no time to be lost: Boone gave the word, “Right about – fire – charge,” and the intrepid hunters dashed in among their adversaries, in a desperate endeavor to reach the fort. 

At the first fire from the Indians, seven of the fourteen whites were wounded, among the number, the gallant Boone, whose leg was broken, which stretched him on the ground. An Indian sprang on him with uplifted tomahawk, but before the blow descended, Kenton, everywhere present, rushed upon the warrior, discharged his gun into his heart, and bore his leader into the fort. When the gate was closed and all things secure, Boone sent for Kenton. ‘Well, Simon,’ said the pioneer, ‘You have behaved yourself like a man to-day; indeed you are a fine fellow.’

This was great praise from Boone, who was a silent man, little given to compliment.”

AHC Note — This account of Simon Kenton saving Daniel Boone is from Collins’ Historical Sketches of Kentucky, written by Lewis and Richard Collins and published in 1874.

Clark’s Kaskaskia Expedition

In 1778, General George Rogers Clark carried out an expedition against Kaskaskia and other towns in the Illinois Country. Simon Kenton served as a scout for General Ckar. When the expedition was over, Clark sent Kenton back to Kentucky, with letters he was to deliver to government officials. Along the way, Kenton and his companions stole some horses from an Indian village. The Indians pursued them and recaptured the horses, but Kenton and the others were able to escape.

George Rogers Clark, Portrait, Longacre
George Rogers Clark. Image Source: National Portrait Gallery.

Attack at Paint Creek

Simon Kenton returned to Kentucky where he and Daniel Boone devised a plan to attack a village on Paint Creek, near present-day Chillicothe, Ohio. Kenton acted as a spy for the expedition.

As he approached the town, he happened to come across two Indians in the wilderness. They did not see him, so he hid and waited for them to approach. When he saw them, he fired on them, killing one and wounding the other.

Kenton went to warn Boone and the others but was quickly attacked by two more Indians. He fought them off and killed them, then hid in the woods, fearing there were more in the area. As he suspected, about a dozen more warriors appeared. They found the bodies of the men Kenton killed and started looking for him.

However, Boone and the others arrived and fired on the Indians, who scattered. Having lost the element of surprise, the attack was called off. Boone and most of the men went back to Kentucky.

Stealing Horses from the Shawnee

After the failed expedition, Kenton and a man known as “Montgomery” remained in the area and managed to steal four horses from the village. They quickly rode back to the Ohio River, crossed back into Kentucky, and made their way to Logan’s Station.

Captured by the Shawnee

Colonel Joseph Bowman sent Kenton, Montgomery, and a man named Clark to scout a Shawnee village on the Little Maumee River in Ohio. While they were there, they saw the Shawnee had some horses that had been stolen from the Kentucky settlements, and decided to steal them back.

They successfully rounded up the horses and headed back to the Ohio River. However, they were discovered and a war party chased after them. Kenton and the others were determined to escape but refused to cut the horses loose.

The chase continued for nearly three days when the men came to the north bank of the Ohio River, at the mouth of White Oak Creek, near present-day Higginsport, Ohio. Kenton and the others camped overnight and tried to cross the river in the morning. However, the river was rough and the horses were unable to cross. They decided to wait another night, in hopes the river would calm down.

The next morning, the river was calm, but the horses refused to swim to the south bank. The men decided to divide the horses between them and ride along the river, southwest to Louisville. As they prepared to leave their campsite, the Shawnee war party caught up to them and attacked. Kenton was taken as a prisoner, Montgomery was killed, and Clark escaped.

Kenton was tied to one of the horses for the journey back to the village, but the Indians decided to use it to torture him. They struck it with a whip and it ran off into the wilderness where Kenton was scratched and bruised by tree limbs. Kenton was able to survive the ordeal but was badly wounded.

Running the Gauntlet

When the group arrived at the village, they were met by Chief Black Fish, who questioned Kenton and then beat him with a hickory switch for stealing the horses. Kenton was tied to a stake while the Indians proceeded to taunt and torture him for most of the night. Eventually, they untied him and put him in one of the buildings for the rest of the night.

The next morning, they woke him up and took him outside, where the villagers were lined up in two rows. Kenton was expected to run between the lines — known as “Running the Gauntlet” — while everyone threw rocks at him or beat him with sticks. If he fell to the ground, he would be attacked and likely killed. If he made it to the end, he would survive and likely be kept as a slave.

Accounts of Kenton’s ordeal with the gauntlet vary. Some say he tried to escape by running away from it, others say he was knocked to the ground several times but was able to survive. He may have even been made to run through a second time. Regardless, when the ordeal ended, the Indians decided to keep him alive.

By this time, Kenton was well-known among the Indians for his prowess in battle with Indians. The villagers decided to take him to the village of Pickaway, near present-day Springfield, Ohio, where he was tortured some more.

From Pickaway, they traveled another 50 miles to Waughcotomoco, in present-day Logan County, Ohio. He was forced to run the gauntlet again and severely beaten, however, he survived and was taken to Wapatomica, where the Shawnee chief Black Hoof lived.

Kenton ran another gauntlet and survived. Afterward, the Shawnee decided to burn him at the stake, however, their plans were ruined by rain.

Saved by Simon Girty

Kenton was held in the village council house. While he was there, his old friend Simon Girty arrived in the village. Girty was allied with the Indians and was also a Loyalist. He had developed a reputation among Americans as a traitor, but also a skilled Frontiersman and fighter. Girty was just as hated by Americans as Kenton was by the Shawnee, and was known as the “White Savage.”

Simon Kenton, Simon Girty, Illustration
This illustration depicts Kenton (left) and Simon Girty (right, with musket). Image Source: Harper’s Monthly, February 1864.

At first, Girty questioned Kenton about the American defenses in Kentucky but did not recognize who he was speaking with. Finally, Girty asked his name, and he replied, “Simon Butler.” Shocked, Girty embraced Kenton and then told the Indians they were close friends and begged them to spare his old friend.

The Shawnee agreed and praised Kenton for his bravery and determination in surviving the gauntlets. 

Kenton spent the next three weeks with Girty, resting and recuperating.

He was also adopted by an old woman, to replace her son, who had been killed. This was according to a traditional Indian custom where slaves and captives were often “adopted” to replace family members who died or were taken away.

Kenton’s Life Threatened Again

Despite Girty’s effort, Kenton was sentenced to die by the Shawnee for a second time. This time, it was for revenge. A Shawnee war party was badly beaten in battle and when they returned to the village they demanded retribution, and decided to take it from Kenton. The Shawnee decided to execute him in Sandusky, which was 50 miles north. The Shawnee escorted him and stopped at many villages along the way to show off their prize. He was beaten at least twice, suffering a broken arm and collarbone. 

Chief Logan Tries to Save Kenton

At one of the villages along the way, Kenton met Chief Logan. Logan and Kenton knew each other and Logan tried to help save Kenton. He sent two messengers to Sandusky with a message, asking for Kenton’s life to be spared. However, when the messengers returned, they told Logan that Kenton was going to Sandusky.

Simon Kenton, Chief Logan, Illustration
This illustration depicts Kenton and Chief Logan. Image Source: Harper’s Monthly, February 1864.

Pierre Drouillard Saves Kenton

Kenton was taken to Sandusky, where he was to be executed. However, around the time he arrived, so did British agent, Pierre Drouillard. He was a trader and interpreter responsible for dealing with the Indians on behalf of British forces at Fort Detroit. Drouillard had received the message from Chief Logan and worked out a deal with the Indians to take Kenton to Fort Detroit, promising to return him when the British were done with him. Drouillard wanted Kenton to provide information on American defenses in Kentucky to his commanding officer, Lieutenant Governor Henry Hamilton.

Fort Detroit

Kenton was at Fort Detroit from October 1777 to July 1779. During this time, he healed and planned his escape. Although his movement in the fort and the surrounding area was restricted, he was involved in some meetings, where he witnessed Lieutenant Governor Hamilton encouraging the Indians to attack American settlements on the frontier. Kenton was also careful to gather intelligence on British plans and defenses. Ultimately, the British failed to keep their agreement with the Indians, and never returned Kenton to Sandusky.

Escape from Detroit and Return to Kenton’s Station

In the spring of 1779, American prisoners were delivered to Fort Detroit. Among them were Kentuckians Captain Nathan Bullitt and Jesse Coffer, whom Kenton knew. Together, they devised a plan to escape from Detroit and go to Louisville — roughly 400 miles south.

By this time, Kenton had created friendships with many people in Detroit. Among them was the wife of a merchant who provided him with guns, ammunition, and supplies. Kenton hid everything in a tree outside the fort. One night in July, Kenton, Bullitt, and Coffer left the fort, retrieved the supplies, and started their dangerous journey to Louisville, Kentucky.

30 days later, they arrived at the Falls of the Ohio, on the Ohio River at Louisville. They successfully avoided the British and Indians for the entire journey. Upon his arrival at Louisville, Kenton sent the information he gathered about the British to George Rogers Clark and then returned to his homestead at Kenton’s Station on Limestone Creek.

Return of Simon Kenton

After returning to Kenton’s Station, he found that some of the new settlers in the area were from the same area in Virginia he originally came from. Although he was still using the name “Simon Butler,” some people recognized him and he admitted he was the Simon Kenton they knew from Fauquier County, Virginia.

From these people, he found out that William Leachman — the man he thought he had killed — was alive. Further, after Kenton disappeared, people accused Leachman of killing Kenton and hiding his body. Knowing he was not wanted for murder, he resumed using his true name.

Clark’s 1780 Expedition

In June 1780, Captain Henry Bird led a combined force of British troops and Indians into Kentucky, where he raided at least three settlements. The settlers appealed to Governor Thomas Jefferson for help and Jefferson responded by ordering George Rogers Clark to organize an expedition to deal with Bird and the Ohio Tribes.

Thomas Jefferson, Painting, Rembrandt Peale
Thomas Jefferson. Image Source: Google Arts & Culture.

Using the information Kenton gathered when he was a prisoner, Clark planned the expedition into the Ohio Country to attack Indian villages along the Mad River and reduce the British presence. 

Kenton served as a scout for this expedition, which included Clark’s victory at the Battle of Piqua (August 8, 1780). This was the largest battle of the American Revolutionary War that took place west of the Allegheny Mountains. 

Afterward, Kenton led Clark and his men to more villages that were destroyed by the Americans, along with the cornfields. Many of the villages were the same ones where Kenton had been tortured or forced to run the gauntlet when he was a prisoner of the Shawnee.

Clark’s 1782 Expedition

In July 1782, Indian leaders and British officials met at the Shawnee villages near the headwaters of the Mad River in the Ohio Country. Various tribes were in attendance, including the Shawnee, Mingo, Wyandot, Miami, Odawa, Ojibwe, and Potawatomi. Officials representing the British Indian Department included Alexander McKee, Simon Girty, and Matthew Elliott. 

Together, they organized an expedition that marched into Kentucky and laid siege to Bryan Station, led by Captain William Caldwell. Caldwell lifted the siege after two days when the Kentucky Militia, led by Colonel John Todd, mobilized and headed to Bryan Station. One of Todd’s officers was Lieutenant Colonel Daniel Boone.

Ultimately, the two forces collided at the Battle of Blue Licks (August 19, 1782). The Americans were ambushed and routed. In the aftermath, George Rogers Clark was criticized for allowing British forces to invade Kentucky. 

Clark responded by organizing an expedition to retaliate for the attacks, and once again he brought in Simon Kenton to help lead his men into Ohio. This expedition, which was the last significant military expedition of the American Revolutionary War, led to the destruction of more villages in Ohio, along the Great Miami River, including Upper Piqua and Loramie’s Store.

Return to Kentucky and Visit to Virginia

Following the expedition, Kenton returned to Kenton’s Station. By then, it was a small village with roughly 20 families living around it and had a grist mill.

In 1783, Kenton returned to his childhood home in Virginia and reunited with his family. While he was there, he recruited people to return with him to Kentucky, including William Leachman. Many accepted the offer and returned to Kentucky with him in 1784. When they arrived, he helped them establish a new settlement on the Salt River.

That same year, he built a blockhouse at Kenton Station to help protect the settlement from attacks by Indians, or British forces that remained on the frontier in the wake of the signing of the Treaty of Paris (1783) that ended the American Revolutionary War and ceded the territory to the United States. He also raised and led a militia company, which was known as “Kenton’s Boys.”

Kenton became involved in land speculation, buying and selling land in Kentucky. He sold his property at Kenton’s Station, which became present-day Old Washington, Kentucky, a part of Maysville. He continued to serve as a guide and scout for settlers and help deal with ongoing attacks and harassment from the Indians.

Northwest Indian War

After Virginia and other states ceded their “Westen Lands” to the Confederation Congress, the United States sent commissioners to negotiate with the Indian tribes living in the Northwest Territory. They successfully negotiated two treaties that gave the United States control of a significant amount of land:

  1. Treaty of Fort McIntosh (1785) — The United States gained most of the lands north of the Ohio River.
  2. Treaty of Fort Finney (1786) — The Shawnee agreed to recognize U.S. control over all lands ceded by Great Britain.

Meanwhile, the Indians continued to raid settlements in Kentucky, despite the treaties. This was the Northwest Indian War, a battle between a confederation of Indian tribes and the United States for control of the Northwest Territory.

The Indians prepared to stop American encroachment into the region. However, Congress passed the Northwest Ordinance of 1787, which organized the territory for settlement. Arthur St. Clair was appointed Governor of the territory and moved to Marietta, Ohio.

From 1785 to 1795, the war carried on. It was finally resolved when American forces under the command of General Anthony Wayne won the Battle of Fallen Timbers (August 20, 1794). The Northwest Indians signed the Treaty of Greenville (August 3, 1795), ending the war.

During the war, Kenton joined Colonel Benjamin Logan in attacks on Indian towns along the Mad River and then served as a Major under General Wayne. Under Wayne, Kenton primarily served as a scout but was not present at Fallen Timbers.

General Benjamin Logan, Portrait
Benjamin Logan. Image Source: Google Arts & Culture.

Marriage to Martha Dowden

Simon Kenton married 17-year-old Martha Dowden in February or March of 1787. Martha’s family was one of those who emigrated from Virginia to Kentucky with Kenton in 1784.

Simon and Martha lived in a brick house on a 1,000-acre farm in present-day Mason County, Kentucky, and had four children. It is believed the brick house was the first built in the county.

Like many Frontiersmen, Kenton lost a significant portion of his land to speculators who took advantage of his inability to read or write.

Death of Matha Kenton and Marriage to Elizabeth Jarboe

Tragedy struck Simon Kenton’s family on December 13, 1796, when the house caught fire. Martha, who was pregnant, died, leaving Simon with the four children.

Kenton still needed to work as a guide, which often kept him away from home. He left the children under the care of a neighbor, Stephen Jarboe. 

Two years later, in 1798, Kenton married Elizabeth Jarboe, Stephen’s 19-year-old daughter. Together, they had five children.

Debtor’s Prison in Kentucky

Kenton loaned money to a man who had been arrested and needed money to pay bail. However, the man disappeared and took the money with him. Under Kentucky law, this made Kenton responsible for the bail. However, he did not have the money to cover the bail, and the court placed him in Debtor’s Prison until it was paid.

Springfield and Urbana

Soon after, Simon Kenton and his family moved to the Mad River Country, a few miles north of Springfield, Ohio. 

During his time living near Springfield, Kenton gained a reputation for being a generous host. He was known for openly welcoming travelers, including Indians who had once captured and tortured him. Today, Kenton’s home outside of Springfield is preserved as the “Historic Simon Kenton Inn.”

Simon Kenton,Springfield Home, Historical Marker, HMDB
This historical marker is in front of the Simon Kenton Inn. It says, “SIMON KENTON. Famed Indian fighter, associate of Daniel Boone and George Rogers Clark, soldier of the Revolution and the War of 1812 — Leading settler of the Mad River Valley, built his first home in Ohio a few hundred feet east of this spot.” Image Source: Waymarking.

Unfortunately, Kenton lost his land outside of Springfield due to a foreclosure. This led him to a meeting in 1803 with a Shawnee chief known as Tecumseh. They agreed to a treaty that granted Kenton large tracts of land in Ohio and Indiana. However, 1803 was the same year Ohio entered the Union and the agreement was voided by the new state government.

Soon after, Kenton settled near Urbana, Ohio, and the Ohio legislature appointed him as a Brigadier General in the Ohio Militia. From that point on, he was often called “General Kenton.”

While living in Urbana, he spent at least two years in prison, due to accusations of failing to pay debts.

War of 1812 and Battle of the Thames

Simon Kenton returned to military service during the War of 1812. At Urbana, Kenton joined an expedition led by General Isaac Shelby and then fought in the Battle of the Thames (October 5, 1813). 

During the battle, Chief Tecumseh of the Shawnee was killed. The Americans knew he had been killed, but were not sure which body was his, so they asked Kenton to identify it. Kenton had great respect for the fallen chief and knew the body would be desecrated, so he pointed to the body of another warrior, whom he knew as Roundhead.

Today, the location of Tecumseh’s body is unknown.

Tecumseh, Illustration, Portrait
Chief Tecumseh. Image Source: Toronto Public Library.

Legal Issues and Kentucky Debtor’s Prison

After the War of 1812, Simon Kenton was plagued by financial issues, primarily for failing to pay his debts. By 1820, he had moved his family near Bellefontaine, Ohio, but he took a trip back to Washington, Kentucky, where he was accused of failing to pay debts, and spent some time in debtor’s prison. He was treated well and released on December 17, 1821, after the Kentucky legislature made changes to the Debtor’s Law. The changes were driven by Kenton’s friends and supporters, who wanted to see him freed from his debts.

Later Years

In 1824, the United States Government granted Simon Kenton a monthly pension. He received $20 a month for the rest of his life, in recognition of his role in helping to open the frontier for America’s Westward Expansion.

Kenton spent the rest of his life living with Elizabeth in a small log cabin on property owned by one of his children.

Attempts to document his life in a biography failed. Had any of them been successful, Kenton might have been catapulted to the same legendary status as Daniel Boone, Davy Crockett, and the famous Mountain Men of the Western Fur Trade.

Death of Simon Kenton

Sinon Kenton died at his cabin on April 29, 1836. He was 81 years old. His body was buried near the cabin, at a spot he had chosen. Kenton’s remains were removed and relocated to Oak Dale Cemetery in Urbana in 1865. 

A monument was eventually built over his grave but was not completed until 1979. The inscription reads:


Who was born April 3, 1755 in Culpepper Co., Va., 
and died April 29, 1836, aged 81 years and 26 days. 
His fellow citizens of the West, will long remember 
him as the skilful pioneer of early times, the brave 
soldier, and the honest man.

Physical Description and Personality

This description of Simon Kenton is from Collins’ History of Kentucky:

“General Kenton was of fair complexion, six feet one inch in height. He stood and walked very erect; and in the prime of life, weighed about one hundred and ninety pounds. He never was inclined to be corpulent, although of sufficient fullness to form a graceful person. He had a soft, tremulous voice, very pleasing to the hearer. He had laughing gray eyes which appeared to fascinate the beholder, and dark auburn hair. He was a pleasant, good humored, and obliging companion. When excited, or provoked to anger, (which was seldom the case,) the fiery glance of his eye would almost curdle the blood of those with whom he came in contact. His rage, when roused was a tornado. In his dealing he was perfectly honest; his confidence in man, and his credulity were such that the same man might cheat him twenty times, and if he professed friendship, might cheat him still.”

Suggested Reading and Resources

  • Simon Kenton, Robert E. Coleman, 1864, from Harper’s Weekly.
  • Collins’ Historical Sketches of Kentucky, Vol 1, Lewis Collins and Richard Collins, 1874.
  • Collins’ Historical Sketches of Kentucky, Vol 2, Lewis Collins and Richard Collins, 1874.
  • Simon Kenton, R.W. McFarland, 1904, from Ohio Archaeological and Historical Publications.
  • Simon Kenton: His Life and Period, 1755–1836, Edna Kenton, 1930.
  • Simon Kenton, Kentucky Scout, Thomas D. Clark, 1993.
  • Simon Kenton, the Pluckiest Woodsman Upon the Ohio Frontier, Charles H.L. Johnston, 1955.