Although many of Harlan County's settlers were too young to have served in the Revolutionary War, several of the early arrivals had served. One of these was Henry Shackleford. Henry Shackleford was born Aug. 30, 1764, in King William Co., Va. He was the son of Henry and Mary Shackleford and had at least one brother, John, for whom he substituted for three weeks during the war, serving under Lafayette.

Henry served three tours of duty in the war in addition to those three weeks substituting for his brother. During his first tour of duty, he participated in the taking of a British brig at Lady Point on the James River. During his second tour of duty, his unit joined Lafayette's Army near Richmond and marched to Culpepper County, Va., where they met General Wayne and his forces. Shackleford believed that Cornwallis was in pursuit of them during this march. After joining with Wayne's forces, they turned on Cornwallis and forced him back across the James River and Jamestown.

Following this second tour he substituted for his brother. His pension application makes mention of no particular incidents during this period. Apparently it was spent marching and camping in the King William area of Virginia. After his brother resumed his place in the unit, Henry was drafted for another two month tour when orders were received in King William County for all the militia captains to collect as many men as possible to go against Cornwallis at Yorktown. According to his pension papers, Shackleford's unit fought a battle near Gloucester, driving the enemy into Gloucester and defeating them there while the army on the other side took Cornwallis.

On Jan. 28, 1785, in Pittsylvania County, Va., Henry married Mary Shields. They appear to have had at least two children before Mary's death, probably in the part of Pittslvania County and later became Henry County. One of these children is believe to be the Joicy Shackleford, born about 1800, who married Stephen Lee.

Henry moved to southeastern Kentucky about 1800. Shortly after his arrival, on Apr 1, 1801, he married Nancy Crump. They settled on Catrons Creek in the part of Knox County that became Harlan in 1819. Henry died in Harlan on May 17, 1842, at the age of 77. After his death, Nancy moved to Bell County where she died.

According to one witness in Henry's pension papers, Henry had prayed and exhorted in public for many years. He was probably of the Methodist faith as he named one of his children after one of the better known circuit riding preachers of his day, Lorenzo Dow. Rev. Dow followed the Methodist doctrine although he was not officially recognized by that church. Henry's son was one of many named after this popular exhorter of the gospel.

Nancy Crump Shackleford applied for a widow's pension after her husband's death and although she states that they raised six children, she names only four of them: Ann Miracle; Elizabeth, wife of William Miracle; Lorenzo Dow, who married Ann Ritta Spurlock; and Nancy Hoskins. A fifth child, Robert L. who married Rachel Lee, is identified from a deed in which he and his sister Nancy Hoskins sell their interest in the land on Martins Fork where their father died. The sixth child is probably the Catherine Shackleford who married William Lee as Henry's widow Nancy is living with them in the 1850 census.