Boone first reached Kentucky in the fall of 1767 while on a long hunt with his brother Squire Boone, Jr. Boone's first steps in Kentucky were near present-day Elkhorn City. While on the Braddock expedition years earlier, Boone had heard about the fertile land and abundant game of Kentucky from fellow wagoner John Findley, who had visited Kentucky to trade with American Indians. Boone and Findley happened to meet again, and Findley encouraged Boone with more tales of Kentucky. At the same time, news had arrived about the Treaty of Fort Stanwix, in which the Iroquois had ceded their claim to Kentucky to the British. This, as well as the unrest in North Carolina due to the Regulator Movement, likely prompted Boone to extend his exploration.
On May 11, 1769, Boone began a two-year hunting expedition in Kentucky. On December 22, 1769, a fellow hunter and he were captured by a party of Shawnees, who confiscated all of their skins and told them to leave and never return. The Shawnees had not signed the Stanwix treaty, and since they regarded Kentucky as their hunting ground, they considered white hunters there to be poachers. Boone, however, continued hunting and exploring Kentucky until his return to North Carolina in 1771, and returned to hunt there again in the autumn of 1772.
On July 5, 1773, Boone packed up his family and, with a group of about 50 immigrants, began the first attempt by British colonists to establish a settlement in Kentucky. Boone was still an obscure hunter and trapper at the time; the most prominent member of the expedition was William Russell, a well-known Virginian and future brother-in-law of Patrick Henry. On October 9, Boone's eldest son James and a small group of men and boys who had left the main party to retrieve supplies were attacked by a band of Delawares, Shawnees, and Cherokees. Following the Treaty of Fort Stanwix, American Indians in the region had been debating what to do about the influx of settlers. This group had decided, in the words of historian John Mack Faragher, "to send a message of their opposition to settlement". James Boone and William Russell's son Henry were captured and gruesomely tortured to death. The brutality of the killings sent shock waves along the frontier, and Boone's party abandoned its expedition.
The massacre was one of the first events in what became known as Dunmore's War, a struggle between Virginia and, primarily, Shawnees of the Ohio Country for control of what is now West Virginia and Kentucky. In the summer of 1774, Boone volunteered to travel with a companion to Kentucky to notify surveyors there about the outbreak of war. The two men journeyed more than 800 miles (1,300 km) in two months to warn those who had not already fled the region. Upon his return to Virginia, Boone helped defend colonial settlements along the Clinch River, earning a promotion to captain in the militia, as well as acclaim from fellow citizens. After the brief war, which ended soon after Virginia's victory in the Battle of Point Pleasant in October 1774, the Shawnees relinquished their claims to Kentucky.
Following Dunmore's War, Richard Henderson, a prominent judge from North Carolina, hired Boone to travel to the Cherokee towns in present North Carolina and Tennessee and inform them of an upcoming meeting. In the 1775 treaty, Henderson purchased the Cherokee claim to Kentucky to establish a colony called Transylvania. Afterwards, Henderson hired Boone to blaze what became known as the Wilderness Road, which went through the Cumberland Gap and into central Kentucky. Along with a party of about 30 workers, Boone marked a path to the Kentucky River, where he founded Boonesborough. Other settlements, notably Harrodsburg, were also established at this time. Despite occasional Indian attacks, Boone returned to the Clinch Valley and brought his family and other settlers to Boonesborough on September 8, 1775.
Violence in Kentucky increased with the outbreak of the American Revolutionary War (1775–1783). Native Americans who were unhappy about the loss of Kentucky in treaties saw the war as a chance to drive out the colonists. Isolated settlers and hunters became the frequent target of attacks, convincing many to abandon Kentucky. By late spring of 1776, fewer than 200 colonists remained in Kentucky, primarily at the fortified settlements of Boonesborough, Harrodsburg, and Logan's Station.
On July 5, 1776, Boone's daughter Jemima and two other teenaged girls were captured outside Boonesborough by an Indian war party, who carried the girls north towards the Shawnee towns in the Ohio country. Boone and a group of men from Boonesborough followed in pursuit, finally catching up with them two days later. Boone and his men ambushed the Indians while they were stopped for a meal, rescuing the girls and driving off their captors. The incident became the most celebrated event of Boone's life. James Fenimore Cooper created a fictionalized version of the episode in his classic novel The Last of the Mohicans (1826).
In 1777, Henry Hamilton, a 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. Boone was shot in the ankle while outside the fort, but he was carried back inside amid a flurry of bullets by Simon Kenton, a recent arrival at Boonesborough. Kenton became Boone's close friend, as well as a legendary frontiersman in his own right.
While Boone recovered, Shawnees kept up their attacks outside Boonesborough, destroying the surrounding cattle and crops. With the food supply running low, the settlers needed salt to preserve what meat they had, so in January 1778, Boone led a party of 30 men to the salt springs on the Licking River. On February 7, 1778, when Boone was hunting meat for the expedition, he was surprised and captured by warriors led by Blackfish. Because Boone's party was greatly outnumbered, Boone returned the next day with Blackfish and persuaded his men to surrender rather than put up a fight.
Blackfish wanted to continue to Boonesborough and capture it, since it was now poorly defended, but Boone convinced him that the women and children were not hardy enough to survive a winter trek. Instead, Boone promised that Boonesborough would surrender willingly to the Shawnees the following spring. Boone did not have an opportunity to tell his men that he was bluffing to prevent an immediate attack on Boonesborough, however. Boone pursued this strategy so convincingly that many of his men concluded that he had switched his loyalty to the British.
Boone and his men were taken to Blackfish's town of Chillicothe, where they were made to run the gauntlet. As was their custom, the Shawnees adopted some of the prisoners into the tribe to replace fallen warriors; the remainder were taken to Hamilton in Detroit. Boone was adopted into a Shawnee family at Chillicothe, perhaps into the family of Chief Blackfish himself, and given the name Sheltowee (Big Turtle). On June 16, 1778, when he learned Blackfish was about to return to Boonesborough with a large force, Boone eluded his captors and raced home, covering the 160 miles (260 km) to Boonesborough in five days on horseback and, after his horse gave out, on foot.
During Boone's absence, his wife and children (except for Jemima) had returned to North Carolina, assuming he was dead. Upon his return to Boonesborough, some of the men expressed doubts about Boone's loyalty, since after surrendering the salt-making party, he had apparently lived quite happily among the Shawnees for months. Boone responded by leading a preemptive raid against the Shawnees across the Ohio River, and then by helping to successfully defend Boonesborough against a 10-day siege led by Blackfish, which began on September 7, 1778.
After the siege, Captain Benjamin Logan and Colonel Richard Callaway—both of whom had nephews who were still captives surrendered by Boone—brought charges against Boone for his recent activities. In the court martial that followed, Boone was found "not guilty", and was even promoted after the court heard his testimony. Despite this vindication, Boone was humiliated by the court martial, and he rarely spoke of it.
After the trial, Boone returned to North Carolina to bring his family back to Kentucky. In the autumn of 1779, a large party of emigrants came with him, including (according to tradition) the family of Abraham Lincoln's grandfather. Rather than remain in Boonesborough, Boone founded the nearby settlement of Boone's Station. He began earning money at this time by locating good land for other settlers. Transylvania land claims had been invalidated after Virginia created Kentucky County, so settlers needed to file new land claims with Virginia. In 1780, Boone collected about $20,000 in cash from various settlers and traveled to Williamsburg to purchase their land warrants. While he was sleeping in a tavern during the trip, the cash was stolen from his room. Some of the settlers forgave Boone the loss; others insisted he repay the stolen money, which took him several years to do.
A popular image of Boone which emerged in later years is that of the backwoodsman who had little affinity for "civilized" society, moving away from places like Boonesborough when they became "too crowded". In reality, however, Boone was a leading citizen of Kentucky at this time. When Kentucky was divided into three Virginia counties in November 1780, Boone was promoted to lieutenant colonel in the Fayette County militia. In April 1781, he was elected as a representative to the Virginia General Assembly, which was held in Richmond. In 1782, he was elected sheriff of Fayette County.
Meanwhile, the American Revolutionary War continued. Boone joined General George Rogers Clark's invasion of the Ohio country in 1780, fighting in the Battle of Piqua on August 7. In October, when Boone was hunting with his brother Ned, Shawnees shot and killed Ned. Apparently thinking that they had killed Daniel Boone, the Shawnees beheaded Ned and took the head home as a trophy. In 1781, Boone traveled to Richmond to take his seat in the legislature, but British dragoons under Banastre Tarleton captured Boone and several other legislators near Charlottesville. The British released Boone on parole several days later. During Boone's term, Cornwallis surrendered at Yorktown in October 1781, but the fighting continued in Kentucky unabated. Boone returned to Kentucky and in August 1782 fought in the Battle of Blue Licks, in which his son Israel was killed. In November 1782, Boone took part in another Clark expedition into Ohio, the last major campaign of the war.
After the Revolution, Boone resettled in Limestone (renamed Maysville, Kentucky in 1786), then a booming Ohio River port. In 1787, he was elected to the Virginia state assembly as a representative from Bourbon County. In Maysville, he kept a tavern and worked as a surveyor, horse trader, and land speculator. He was initially prosperous, owning seven slaves by 1787, a relatively large number for Kentucky at the time. Boone became a celebrity while living in Maysville. In 1784, on his 50th birthday, historian John Filson published The Discovery, Settlement And present State of Kentucke, a book which included a chronicle of Boone's adventures.
The Revolutionary War had ended, but the border war with American Indians north of the Ohio River resumed with the Northwest Indian War. In September 1786, Boone took part in a military expedition into the Ohio Country led by Benjamin Logan. Back in Limestone, Boone housed and fed Shawnees who were captured during the raid, and helped to negotiate a truce and prisoner exchange. Although the war escalated and would not end until the American victory at the Battle of Fallen Timbers in 1794, the 1786 expedition was the last time Boone saw military action.
Boone began to have financial troubles while living in Maysville. According to the later folk image, Boone the trailblazer was too unsophisticated for the civilization which followed him and which eventually defrauded him of his land. Boone was not the simple frontiersman of legend, however: he engaged in land speculation on a large scale, buying and selling claims to tens of thousands of acres. The land market in frontier Kentucky was chaotic, and Boone's ventures ultimately failed because his investment strategy was faulty and because his sense of honor made him reluctant to profit at someone else's expense. According to Faragher, "Boone lacked the ruthless instincts that speculation demanded."
Frustrated with the legal hassles that went with land speculation, in 1788, Boone moved upriver to Point Pleasant, Virginia (now West Virginia). There he operated a trading post and occasionally worked as a surveyor's assistant. When Virginia created Kanawha County in 1789, Boone was appointed lieutenant colonel of the county militia. In 1791, he was elected to the Virginia legislature for the third time. He contracted to provide supplies for the Kanawha militia, but his debts prevented him from buying goods on credit, so he closed his store and returned to hunting and trapping.
In 1795, Rebecca and he moved back to Kentucky, living in present Nicholas County on land owned by their son Daniel Morgan Boone. The next year, Boone applied to Isaac Shelby, the first governor of the new state of Kentucky, for a contract to widen the Wilderness Road into a wagon route, but the contract was awarded to someone else. Meanwhile, lawsuits over conflicting land claims continued to make their way through the Kentucky courts. Boone's remaining land claims were sold off to pay legal fees and taxes, but he no longer paid attention to the process. In 1798, a warrant was issued for Boone's arrest after he ignored a summons to testify in a court case, although the sheriff never found him. That same year, the Kentucky assembly named Boone County in his honor.
Daniel Boone died of natural causes, other sources, from acute indigestion on September 26, 1820, at Nathan Boone's home on Femme Osage Creek, 2-1/2 months short of his 86th birthday. His last words were, "I'm going now. My time has come." He was buried next to Rebecca, who had died on March 18, 1813. The graves, which were unmarked until the mid-1830s, were near Jemima (Boone) Callaway's home on Tuque Creek, about two miles (3 km) from the present-day Marthasville, Missouri.
In 1845, the Boones' remains were supposedly disinterred and reburied in a new cemetery Frankfort Cemetery in Frankfort, Kentucky. Resentment in Missouri about the disinterment grew over the years, and a legend arose that Boone's remains never left Missouri. According to this story, Boone's tombstone in Missouri had been inadvertently placed over the wrong grave, but no one had ever corrected the error. Boone's relatives in Missouri, displeased with the Kentuckians who came to exhume Boone, kept quiet about the mistake, and they allowed the Kentuckians to dig up the wrong remains.
No contemporary evidence indicates this actually happened, but in 1983, a forensic anthropologist examined a crude plaster cast of Boone's skull made before the Kentucky reburial and announced it might be the skull of an African American. Black slaves had also been buried at Tuque Creek, so it is possible the wrong remains were mistakenly removed from the crowded graveyard. Both the Frankfort Cemetery in Kentucky and the Old Bryan Farm graveyard in Missouri claim to have Boone's remains.