Dolly Dolly was the enslaved servant of Richard Callaway whom he brought to Kentucky in the party that Daniel Boone led through the Cumberland Gap to settle Boonesborough in April 1775. She and Susannah Hays, Boone’s daughter, were the first women at the fort. Susannah and Dolly cooked and tended camp for the woodcutters during the epic journey. Richard Callaway was killed by Indians in 1780. Dolly was one of three slaves listed in his will, wri…