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).