Purchase Print Old Fort Harrod State Park and the Gunpowder magazine (in front) in Harrodsburg, Kentucky. Founded in 1774, Harrodsburg is the oldest, and first permanent settlement in Kentucky. It was founded by James Harrod, a pioneer, soldier, and hunter who helped explore and settle the area west of the Allegheny Mountains. Its residents included Squire Boone, the younger brother of Daniel Boone