Simon Kenton: Frontiersman, Soldier, Spy

By late April of 1777, nerves were on edge for the fifteen or so families taking refuge in the stockade at Boonesborough, including a few enslaved people and a handful of rifleman. Since early March, settlers there had been forced to venture out from the safety of the fort in small groups in order to ready their fields for the spring planting. Armed guards accompanied the farmers as they were under constant threat of Indian attack.

Chief Blackfish and roughly 200 Shawnee warriors had crossed south of the Ohio that spring, establishing a base camp near the Licking River from which they could launch sustained attacks on the Kentucky strongholds of Harrodsburg, Logan’s Station, and Boonesborough. Conditions in the American stockades were cramped. A couple of young hunters were scouting for the three settlements, carrying messages back and forth, and providing meat. One was a tall young man from Virginia known as Simon Butler. He had been in Kentucky since serving in Lord Dunmore’s war in 1774 but in April 1777 he was fairly new to Boonesborough. He was hard and tough; a man “with the bark on.” He happened to be at the fort on the morning of Thursday, April 24th.

The cows had inexplicably refused to go out to pasture that morning. The leader of the settlement, Daniel Boone, sent two men out to have a look around. Simon Butler, among others, kept a watch at the gate, long rife in hand. After venturing out several yards and finding nothing amiss, the two men turned back toward the fort. Suddenly shots rang out from the sycamore hollow nearby. The Kentucky men raced for the open gate; one man was shot down. Quickly a small group of Shawnee set upon him, lifting his scalp. As a warrior hoisted the bloody trophy and shook it in triumph toward the fort, Simon Butler moved forward, drew a bead on the man and shot him dead.  The other warriors dispersed.

Butler joined Boone and a few other men who raced out of the fort in pursuit of the fleeing Indians; but it was a trap. Soon another group of Shawnee formed up behind the Kentucky men, blocking their return to the safety of the fort. “Boys, we have to fight.” Boone yelled. “Sell your lives as dear as possible!” The Kentucky men rushed back toward the Indians; shouts were raised, more shots were fired, knives and tomahawks were slashing as the bodies of the contenders slammed into each other. Several men were wounded, Boone among them. He went down when a ball shattered his ankle. It would trouble him for the rest of his life. Quickly a Shawnee warrior straddled Boone’s fallen body with tomahawk raised, ready to cleave in his skull. Simon Butler put a rifle ball through him; the warrior fell. A second Indian came up to finish the job with knife in hand. Not having time to reload, young Butler swung his clubbed rifle like a Louisville Slugger, smashing the man’s skull. With adrenaline running high, he reached down and grabbed Boone, hefting him upon his shoulder. Butler then made for the gate through a hail of bullets, thus saving both their lives. Though some had been bloodied, the Kentucky men managed to reach the fort. The gunfire eventually slackened; the warriors dispersed. The fight was over.

Kenton Saves Boone
Kenton Saves Boone

Later, from his bed, Boone sang out high praise for the young Virginian. “Simon”, he said, “you have behaved like a man today. Indeed, you are a fine fellow.”

In 1777, Simon Butler was a man of the west but he was also a young man on the run; and running under an assumed name. His real name was Simon Kenton and, as far as he was concerned, he was wanted for murder back in Virginia. Born in the Bull Run Mountains in 1755, in what was then part of Prince William County, Kenton remembered his mother always said he had been born “in the April before Braddock’s defeat.” In 1770, when he was 15 years-old, Simon became infatuated with a young girl in the settlement named Ellen Cummins. Unfortunately for him, she was betrothed to a slightly older fellow named William Leachman. Opportunities to meet and socialize with far-flung neighbors were rare for the poor tenant farmers of the settlement so, on the day of the wedding, the meeting house was full. Young Simon showed up as well; he was angry and, according to some, bare-chested. He challenged the older Leachman to step outside and settle the matter.  William Leachman decided to accommodate the boy.

The day didn’t end well for Simon Kenton. Not only did he lose the girl he loved but he was badly beaten in front of the whole settlement to boot. It wasn’t over though; not for Simon Kenton. A year would pass. Now 16, taller, stronger, he had even learned a little about fighting. When one day his father sent him over to the Leachman farm to borrow a saw, Simon grabbed his chance for revenge. Walking along together on a wooded path leading to a small clearing where William Leachman had left the saw, Simon suggested to Leachman that it was a good place for Round 2. As they had a year before, the two young men began to fight. Although he was giving a better account of himself this time around, young Simon quickly learned that he had put too much stock in his own abilities; he was beginning to get the worst of it. But, during the scrap he worked out a plan; maneuvering Leachman to the other side of the clearing and then knocking him down, Kenton proceeded to pounce on his opponent, tangling Leachman’s queued hair in the branches of a small sapling. With Leachman unable to escape for the moment, Simon’s pent-up range unleashed itself in savage blows to the older man’s head and face. When the punches finally ceased, Simon saw blood coming from Leachman’s nose and mouth; he was slumped against the sapling. Calming down, Simon untangled Leachman’s hair from the sapling and tried his best to revive him. But William Leachman was out for the count. In that moment a panic swept over the teenaged Kenton that he couldn’t shake. Indeed, he convinced himself that Leachman was, in fact, dead.

Still hampered by waves of panic, Simon knew he couldn’t go home as he was fully aware of what his fate would be were he to be caught and convicted of murder. Not wishing to go to the gallows, he fled into the forest where he hid out all night. By the next morning a plan had formed in his mind: he would leave home; he would head west. Simon Kenton had an uncle, Thomas Kenton, who worked as an Ohio River Indian trader, out of Fort Pitt. He had told stories of the Indians with whom he traded, like the Shawnee, who lived north of the Ohio. South of the river, he told of a land known as the Middle Ground. No one lived there, as far as he knew; it was more or less an Indian hunting preserve for the various tribes, including the Cherokee to the south. But Thomas Kenton told of the vast herds of game in the Middle Ground and of the cane fields he had seen. His nephew Simon had always wanted to see this land so, as a result of his current state of affairs, he made up his mind then and there to travel to Fort Pitt and then down the Ohio River to see the Middle Ground and those cane fields for himself. The next day, hatless and shoeless, with only “a shirt and a pair of course tow linen pantaloons all stained with blood which he washed off with leaves and water” he began his journey west.

He stopped at farms along the way, asking for food and, more often, performing work, like chopping wood for the winter fire to earn a meal. When he reached the settlement of Warm Springs, VA, having traveled well over 100 miles, every step of the way by foot, he met a kind miller named Jacob Butler. The miller gladly took the boy in and gave him work, believing he was, perhaps, a distant relative. Simon stayed in Warm Springs for nearly two months. Before he set out again for Fort Pitt, Jacob Butler had seen to it that the boy had what he needed to survive in the west; namely, a long rifle, powder horn and shot pouch. Simon took with him something else, as well; a new name. For the next eight years he would be known as Simon Butler.

Gear2Simon Kenton made it to Fort Pitt. He learned to hunt, trap, read sign, and shoot straight. He made a name for himself as a woodsman. Because of this, he served in Lord Dunmore’s war as a scout and during that time met and befriended such notable young men as Simon Girty, who would change sides and serve with the British and Indians during the Revolution and George Rogers Clark. In 1778, during his bid to conquer the Old Northwest, Clark used Kenton to scout and spy out the Wabash town of Vincennes. That same year, Simon was captured by the Shawnee on the north side of the Ohio and spent over a month in captivity, being forced to run what was known as “the Gauntlet” as many as nine times. Condemned to die, the Shawnee named him Cut-ta-ho-tha, meaning condemned man. Expecting death at any moment, he suffered severe beatings and broken bones, was adopted by an old Shawnee woman and, ultimately, after being taken to Detroit, was able to make his escape back to Kentucky.

Indian raids continued. In 1780, leading a company of militia, Kenton once again ventured north of the Ohio River as he served under Gen. George Rogers Clark in his campaign against the Shawnee towns of Chillicothe and Pickaway Town.

It is believed that in 1779, after meeting some new arrivals to Kentucky from his old home county in Virginia, Simon was surprised to learn that his old enemy, William Leachman, was actually still alive! In fact, due to Simon’s sudden disappearance from the area, Leachman himself had undergone suspicion of murder.  With the news that Leachman was alive and well, Simon was able to reclaim his true identity. In 1783, after not seeing his family for 12 years, Simon Kenton returned to Virginia. He was able to persuade several members of his family, including his parents, to return to Kentucky with him, providing land for all. Sadly, his father, Mark Kenton, Sr., aged and in ill health, died along the way.

After the Revolution, Simon Kenton built a blockhouse on Limestone Creek, near present-day Maysville, KY, and established Kenton’s Station. Over the years, he made a practice of meeting new settlers coming down the Ohio and safely guiding them inland to his station and other established settlements. He surveyed and helped locate lands for various warrant holders, taking as his payment a portion of the claims. He was also able to make claims himself, thus acquiring thousands of acres of Kentucky lands, some of which he deeded over to new arrivals.

In 1794, Simon Kenton served under General “Mad” Anthony Wayne in his successful campaign against the Shawnee and Miami tribes but, because of illness, he missed the climactic Battle of Fallen Timbers. He married twice, fathering 8 children. At the dawn of the 19th century, once the Indian threat was over, he moved his family north to the Ohio territory. He would later be promoted to Brigadier General of State Militia. By 1810, the Kenton’s were settled in the town of Urbana.

Due to lose land laws and, in some cases, non-payment, his land claims in both Kentucky and Ohio began to fail. In 1811, a Kentucky claimant sent lawyers to Ohio to collect on a debt against Kenton. Kenton refused to pay, as he thought it was not a legal claim. He was arrested under the old Debtor’s Law & remanded to the Urbana jail until the debt was paid.

In a demonstration of how well respected he was, the people of Urbana, OH elected Simon as town jailor, thus making him his own keeper. He had free reign of the town. Carrying a walking stick instead of his rifle, he walked wherever he wished in the town limits of Urbana. He served 1 year before being released. The record doesn’t indicate if the debt was ever paid.


During the War of 1812, at the age of 58, Simon Kenton began organizing scouting parties again. When the governor of Kentucky and old Revolutionary War comrade, Isaac Shelby, marched through Urbana on his way to join William Henry Harrison on the frontier, Kenton joined up. He had no official military function he said, but went along “on his own hook”. He fought in the Battle of the Thames, in 1813. This battle saw the death of the great Shawnee leader, Tecumseh. Having met Tecumseh on a few occasions, Kenton was asked to identify the body. The body of Tecumseh was located but, knowing how the American soldiers would defile it, Kenton purposely misidentified another fallen chief as Tecumseh.

Simon Kenton was one of the founding settlers of Kentucky and Ohio and was well known on the frontier. Like his friend Daniel Boone, he would acquire and later lose thousands of acres of Kentucky lands. Also like Boone, he would come to form warm friendships with some of the aging Shawnee warriors who had kept him in captivity during the Revolution. He died in Ohio in 1836 at the age of 81; he is buried in Urbana. Though well-known during his lifetime, he faded into obscurity as the years passed, being overshadowed by the likes of Boone, Davy Crockett and later heroes like Kit Carson. By the early 20th century, Kenton’s exploits were hardly known. Were it not for a handful of individuals, however, including 4 of his children, Kenton’s story may well have been forgotten with the passage of time.

Lyman Draper
Lyman C. Draper

In 1838, professing a keen interest in the history of the Revolution and the western frontier, historian and librarian Lyman C. Draper began traveling what he called the Trans-Allegheny West, interviewing aging pioneers in order to capture and preserve the oral histories of the frontier before they faded from living memories. Interviews Draper conducted with Kenton’s friends, children, and various other relatives were preserved in a collection of manuscripts that are now housed in the Wisconsin Historical Society. Though his research on the early frontier was extensive, Draper never got around to publishing a definitive work. Likewise, a biography planned, but never published, by one Judge John H. James  of Urbana, OH, yields a great many facts on Kenton based on copious notes the judge took down when meeting with old Kenton himself in Ohio in 1832. Other than being able to write his own name, Simon Kenton was illiterate throughout his life. These interviews, therefore, are perhaps the closest we can come to Kenton’s own voice. Indeed, Judge James admitted that he enjoyed Kenton’s “racy dialect”.

In 1930, using the primary sources from Judge James and the Draper manuscripts, one of Kenton’s descendants, famed writer and literary critic Edna Draper, published a biography of her ancestor: Simon Kenton His Life and Period 1755 – 1836.

The frontier had its share of folklore but, through the efforts of Lyman Draper, Judge James, children and relatives, we cannot deny that Simon Kenton, Virginian, Kentuckian, Ohioan, soldier, scout, and spy………..passed this way.

Old Simon Kenton
Simon Kenton

6 thoughts on “Simon Kenton: Frontiersman, Soldier, Spy

  1. BillF

    Thank you for this article. I first discovered Kenton in Allan Eckert’s book “The Frontiersman.” It was a fascinating time in American history that few people know about, and he certainly hasn’t gotten the recognition he deserves,

    Liked by 1 person

    1. Thank you for leaving your comment. I, too first learned of Simon Kenton from Echert’s “The Frontiersman”. I was excited many years ago to learn he was born only about an hour from my home in Richmond!


    2. Rusty Spiars

      BillF, years ago I read a great book about Kenton. Is the book you mentioned a biography of Kenton, or are there various sections about various frontiersmen. The one I read was about Kenton only. Thanks


  2. Jim Bolton Hodges

    I went to Simon Kenton High School and it’s good to see this great pioneer remembered. Well done, a fine read.


  3. Linda Knight

    Simon Kenton is my 5th great grandfather, and I have begun research on this amazing man. Thank you for your excellent article. Wonderful Information.


  4. M. Scott

    My Hero! Have read the Frontiersmen! Also A Sorrowinour Heart. Both books by Allen W. Eckert. I live 45 miles from Harrodsburg, Ky.


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