Randolph Bobbitt was born in 1796 in Grayson County Virginia. He was a son of William Bobbitt Junior and Nancy (Clifton) Bobbitt. He was a grandson of Captain William and Nancy (McKenzie) Bobbitt.
Randolph Bobbitt served in the war of 1812. He was a private in the company of Captain Trimble, in the Seventh Regiment of the Virginia Militia, commanded by Colonel David Saunders. Randolph volunteered as a substitute for Lewis M. McClain who was drafted to serve in that war. When Randolph was 18 years of age, he entered the army service on August 4, 1814, and was discharged on March 4, 1815, at Fort Baber, near Norfolk, Virginia.
Captain William Bobbitt, grandfather of Randolph Bobbitt, died in 1817. Before the death of his grandfather, Randolph Bobbitt married Rachel Phillips, a distant cousin, and the marriage was recorded in Grayson County Virginia. The marriage bond was dated March 28, 1815, and William Bobbitt was the surety for the marriage. On April 24, 1820, William Bobbitt Junior, the father of Randolph, deeded property to Randolph which was recorded in Grayson County in Deed Book 4, pages 160-161.
"This indenture between William Bobbitt of Grayson County, and Randolph Bobbitt of Grayson County, for 40 dollars, a parcel of land containing 40 acres of land in Grayson County, on Big Reed Island Creek."
Witnesses: James Bobbitt WILLIAM BOBBITT
John Bobbitt Junior, Robert Bobbitt
A comparison of the costs of land at the time indicates that this land deed was a gift from William Bobbitt to his son Randolph and the money transaction was to have the deed legally recorded.
Randolph Bobbitt was the first son of William Bobbitt Junior. He had a second son who was not born until 1821 named William Bobbitt. On March 20, 1824, Randolph Bobbitt sold this same 40 acres of land to his brother-in-law, George Hill of Grayson County, for three hundred dollars. The land was sold through William Bobbitt Junior, father of Randolph, who had been given power of attorney to act on his behalf. Randolph Bobbitt at the time was living in Pulaski County Kentucky. Randolph and his family were counted in the 1820 census of Grayson County, but moved to Pulaski County Kentucky in 1823, where he lived until 1845.
Randolph was for his time, an educated man. He could read and write. He had knowledge of the workings of the law and in Kentucky served as Justice Of The Peace for many years. He also wrote letters between the pioneers of Kentucky and Virginia. Apparently he received his education in the log cabin schools of Grayson County Virginia.