The mountains of Rockcastle County were the last challenge pioneers faced before reaching the level land of the bluegrass area. In the 1700's, three routes in the county were traveled by thousands of pioneers by 1790. The first was Skaggs Trace, a rugged hunting trail traveled and named for the legendary Long Hunter Henry Skaggs, initially beginning at present day Flat Lick, Kentucky, to Crab Orchard and passing through Old Hazel Patch near present day Oakley, Kentucky. It followed the ridge lines and also Skaggs Creek south of Mount Vernon. Boone Trace was marked by Daniel Boone and a crew of thirty men in 1775. It brought travelers on foot or horseback through the Cumberland Gap and ended at Fort Boonesborough. It followed Skaggs Trace from Flat Lick to Old Hazel Patch, where Boone left the old road to proceed north. The Wilderness Road was commissioned by Isaac Shelby, Kentucky's first Governor, and the contract was given to James Knox and Colonel Joseph Crockett to construct a road thirty feet wide that could accommodate a two-ton wagon load. Construction was to begin in Crab Orchard and end at the top of the Cumberland Mountain in the Gap. Knox and Crockett and surveyors held a meeting at Stephen Langford's Station in Mount Vernon and decided to incorporate the road Langford built from Mount Vernon to Livingston as part of the Wilderness Road, currently approximating the route of U.S. 25. Segments of Boone Trace were rebuilt and became part of the new wagon road, the Wilderness Road. Although construction of the Wilderness Road is often attributed to Boone, he was not involved with that endeavor.