From 1767 to 1771, he went on several
long hunts, with his brother, Daniel, into the
Kentucky wilderness. In 1775,
Richard Henderson, a prominent judge from North Carolina, hired Daniel Boone to blaze what became known as the
Wilderness Road, which went through the
Cumberland Gap and into central Kentucky. Squire Boone accompanied his brother and 30 others, assisting in the settlement of
Boone's Station (present-day Boonesborough). In Spring 1779, after the
siege of Boonesborough, where Squire had a rifle ball cut out of his shoulder, he moved his family to the settlement at the
Falls of the Ohio that would become
Louisville. In 1780, he brought 13 families to "Painted Stone", a tract of land in Shelby County, and established
Squire Boone's Station there, the first permanent settlement in the county. He was wounded in April 1781 when Indians attacked the fort; complications of the gunshot injury would result in his right arm being an inch and a half shorter than his left. On September 13, 1781, the settlers abandoned the undermanned station and headed for nearby
Linn's Station. Since Squire Boone was still too weak from his injury to make the trip, he stayed behind at the station with his family and one other. The fleeing settlers were attacked in what became known as the
Long Run Massacre. In 1782, he began acting as a land locator for wealthy land speculators who did not want to personally risk living on the frontier. However, due to financial losses in this line of work, he lost his own property, including the station, in 1786 and was forced to settle elsewhere in the county. He served two terms in the
Virginia legislature in 1789 and 1790 and was the primary sponsor of a bill to charter the town of Louisville. ==Life in Indiana==