Adapted from the Wikipedia article about Daniel Boone
After the American Revolution, Daniel Boone resettled in what was then known as Limestone, which was later renamed to Maysville Kentucky (1786). Limestone at the time was a booming Ohio River port. He was elected to the Virginia state assembly as a representative from Bourbon County (a vast region that included in part the present day Mason 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, which was dominated by small farms rather than large plantations. Boone became something of a celebrity while living in Maysville: in 1784, on Boone's 50th birthday, historian John Filson published The Discovery, Settlement And present State of Kentucke, a book which included a chronicle of Boone's adventures.
Although the Revolutionary War had ended, the border war with American Indians north of the Ohio River soon resumed. 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 Northwest Indian 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. These ventures ultimately failed because of the chaotic nature of land speculation in frontier Kentucky, as well as Boone's faulty investment strategy and his lack of ruthless business instincts.
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, and so he closed his store and returned to hunting and trapping.
In 1795, he and Rebecca (Boone's wife) 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 governor did not respond and 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 Kentucky named Boone County in his honor.