It is estimated up to 300,000 people traveled down the Wilderness Road from 1775-1810. Many were on their way to settle north into Kentucky and other lands west of the Cumberland Gap. What made folks stop where they did? “Just off the Wilderness Road” asks this question.
In 1750, Dr. Thomas Walker partnered with Peter Jefferson (father of Thomas Jefferson) and started the Loyal Land Company. Walker journaled details of over 800,000 acres in southwest Virginia. He and his group traveled through the Cumberland Gap into Kentucky and even built a small cabin.
In 1769, Joseph Martin built Martin Station where Rose Hill, Virginia is today. On March 17, 1775, Richard Henderson’s Transylvania Company purchased much of the land (32 million acres) that is now Kentucky and Tennessee from the Cherokee through a treaty signed at Sycamore Shoals on the Watauga River. They paid in supplies and trade goods, equal to approximately 10,000 British Pounds (value of only $1.5 million U.S. in 2016). Soon after, Henderson hired Daniel Boone to blaze a trail through southwest Virginia into Kentucky.
Many settlers that followed would have purchased land from agents of the Transylvania Company or other similar organizations. Due to limited mapping, disputes and confusion of property ownership were common. Undoubtedly, there were instances of people stopping where it was necessary and finding a suitable place to settle. This was the case for the fictitious William Davis mentioned in this song.
