On June 16, 1774 Harrodsburg became the first permanent Kentucky settlement. Harrodsburg was also the first white settlement west of the Allegheny Mountains. James Harrod founded Harrodsburg and its original name was Harrodstown. Harrodsburg almost floundered when Indians scared most of the whites off in 1774, but it was firmly reestablished in 1775. Harrodsburg’s initial population was 40-50 people and agriculture was the bases for Harrodsburg society. In 1778, Harrodsburg’s population was 198. Harrodsburg was made the county seat of Kentucky (At this time Kentucky was still a county in the state of Virginia). Harrodsburg is the oldest city west of the Allegheny Mountains. It is still located in Mercer County.

Daniel Boone established Boonesbourgh in 1775. Daniel Boone worked for the Transylvania Company, which was owned by Judge Richard Henderson. Boone set out to blaze a trail to the Transylvania Colony. The goal of Boone and Henderson was to become wealthy by accumulating land in the west. At this time Kentucky was known as Transylvania, which means beyond the mountains. Boonesbourgh was to be the capital of the Transylvania Colony. It was located on the banks of the Kentucky River in what is now Madison County. When Boonesbourgh was first settled, Henderson wanted a fort a built. It took three years for the fort to be built, because of laziness (settlers wanted to build their own cabins and grow crops for themselves, instead of worrying about the community as a whole) and since the Indians had withdrawn they felt safe. The first part of the fort that was built was a powder magazine, followed by a rectangular fort with 4 block towers at the corners and a central gate. The Indians returned along with the French Canadians in 1778, and laid siege to Fort Boonesbourgh. Boonesbourgh won out and in 1779 became a chartered town of Kentucky. In 1788 Boonesbourgh became a tobacco inspection station and was prospering. By 1810, there were only 68 people in 8 households left in Boonesbourgh. By 1840 Boonesbourgh had disappeared. There is now a fort and tourist center located close to where the original fort was, but Boonesbourgh never made a come back.