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.In 1776, two of Callaway's daughters, along with Boone's Jemima, were kidnapped outside Boonesborough by Native Americans.