Richard Callaway

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. Callaway led one of parties in the famous rescue of the girls. His nephew Flanders Callaway later married Jemima Boone. In April 1777, Callaway and John Todd were elected to the Virginia legislature as burgesses from Kentucky County, Virginia. In June 1778, he was appointed a justice of the peace and made colonel of the county’s militia.

Callaway was a defender during the 1778 siege of Boonesborough. He disagreed with some of Boone’s actions and resented the younger man’s popularity with the settlers, and later brought court martial charges against Boone. Callaway was angry when the court acquitted and then promoted him.

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.