Richard Callaway (June 14, 1717 – March 8, 1780) was an early settler of Kentucky. Born in Caroline County, Virginia, Callaway joined Daniel Boone in 1775 in marking the Wilderness Road into central Kentucky, becoming one of the founders of Boonesborough, Kentucky. He took part in organizing the short-lived colony of Transylvania. On March 8, 1780, Colonel Richard Callaway was ambushed about a mile outside of Boonesborough by a Shawnee war party. He was killed and scalped, and his body was mutilated. Despite being spelled differently, Calloway County, Kentucky, was named after Callaway.