William Bobbitt was born in Grayson County Virginia in 1816. He was the fifth son of the six sons of John and Nancy (Nuckolls) Bobbitt of Grayson County Virginia. He was three years old when his father died. William was reared by his mother Nancy Nuckolls Bobbitt, who was a strong woman from a family of much character and wealth in Grayson County. Nancy Bobbitt never remarried after the death of her husband. She guided and raised to maturity her six sons on the farm of her husband in Grayson County.
John Bobbitt the father of William was a son of Captain William Bobbitt who served in the war of the Revolution. In the vicinity they lived in were numerous members of the Bobbitt family. One of these members was Randolph Bobbitt a first cousin to William Bobbitt. Randolph Bobbitt married Nancy Phillips of Grayson County. The sons and daughters of Randolph and Nancy Bobbitt were near the ages of the sons of John and Nancy Bobbitt.
During the 1820's the members of the Bobbitt family began to migrate to Pulaski County Kentucky for better soil in which to farm, and to escape the higher taxes imposed on tobacco crops, slaves and property. Among the first of these Bobbitt families to leave Grayson County was Randolph and Nancy (Phillips) Bobbitt. They left Grayson County in 1824 and moved to Pulaski County where they lived near relatives who had moved to Kentucky several years earlier. Randolph and Nancy Bobbitt had a daughter named Nancy who was born in 1816 and was eight years old when she moved with the family to Kentucky.
The family was listed in the 1820 census of Grayson County Virginia as:
Randolph Bobbitt (born 1796)
1 male under 10 (1810-1820) 2 females under 10 (1810-1820)*
1 male 16 - 24 (1784-1796) 1 female 16 - 26 (1794-1804)
*One of the daughters listed here was Nancy Bobbitt, who would later in Pulaski County Kentucky marry William Bobbitt of Grayson County Virginia. Nancy was a first cousin once removed from William Bobbitt. The father of William Bobbitt, and the grandfather of Nancy were brothers.
The family of William Bobbitt who was living with his widowed mother in Grayson County Virginia was counted in the 1820 census as:
Nancy Bobbitt: (born 1790, widow of John Bobbitt)
4 males under 10* (1810-1820) 1 female 26 - 45 (1775-1794)
2 males 10 - 16 (1804-1810)
*One of these four males was William Bobbitt who later married Nancy Bobbitt in Pulaski County Kentucky.