On March 10, 1775, Boone and around 30 other ax-wielding road cutters (including his brother and son-in-law) set off from the Long Island of Holston River, a sacred Cherokee treaty site located in present-day Kingsport, Tennessee. From there they traveled north along a portion of the Great Warrior’s Path, heading through Moccasin Gap in the Clinch Mountains. Avoiding Troublesome Creek, which had plagued previous travelers along the route, Boone’s group crossed the Clinch River (near what is now Speers Ferry, Virginia) and followed Stock Creek, crossed Powell Mountain through Kane’s Gap and headed into the Powell River Valley.
About 20 miles from the Cumberland Gap, Boone and his party rested at Martin’s Station, a settlement near what is now Rose Hill, Virginia that had been founded by Joseph Martin in 1769. After a Native American attack, Martin and his fellow settlers had abandoned the region, but they had returned in early 1775 to build a more permanent settlement. Just before reaching their intended settlement site on the Kentucky River in late March, Boone’s group was attacked by some of the Shawnee, who unlike the Cherokee had not ceded their right to Kentucky’s land. Most of Boone’s men were able to escape, though a few were killed or injured. In April, the group arrived on the south side of the Kentucky River, in what is now Madison County, Kentucky.