 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.