On April 21, 1775 Floyd began preparing to re-enter Kentucky through Cumberland Gap. Floyd took a party of 32 men to Dix River in 1775 to set up a camp. Only twenty miles from Boonesborough, Kentucky which was founded by Daniel Boone on the Kentucky River. On May 23, 1775 Floyd was sent as a delegate from the settlement of St. Asaph to Boonesborough to meet to agree on laws and regulations for requirements to establish a colony called Transylvania. This marked the earliest form of any government west of the Allegheny Mountains. During the summer of 1776 he was living in Boonesborough and accepted the surveyor of Transylvania by Richard Henderson the leader of the colony attempt.