Years before entering Kentucky, Boone had heard about the region’s fertile land and abundant game. In 1767, Boone and his brother Squire first crossed into what would become the state of Kentucky, but they failed to reach the rich hunting grounds. In May 1769, Boone set out again with a party of five others, beginning a two-year hunting expedition in which Boone thoroughly explored Kentucky. His first sighting of the Bluegrass region from atop Pilot Knob became "an icon of American history," and was the frequent subject of paintings.