We do not know exactly when James Bobbitt went to Grayson County. There is no record of a marriage for James before he married Rosanna Bobbitt, his first cousin. The 1820 and 1830 census show that two brothers and a sister of James Bobbitt were living with him and Rosanna. Their father John Bobbitt died in Grayson County in 1816 and is buried in what is today Hills, Virginia in Carroll County. The two brothers were Lacy Bobbitt who died in the Way of 1812 and Vincent Bobbitt who moved to Fleming County, Kentucky. Matilda Bobbitt the sister seems to have married and stayed in Grayson County, Virginia.
Robert Jones, a minister of the Gospel, married James Bobbitt and Rosanna Bobbitt on February 16, 1799 in Grayson County, Virginia and the marriage is recorded. Rosanna Bobbitt was a first cousin to James, an d a daughter of Captain William Bobbitt. She was married with her father's consent. Rosanna was 24 years of age and James was 31 years of age.
James Bobbitt acquired a considerable quantity of land in Grayson County which was located near to Captain William Bobbitt and his family. Much of this land was bounty land which came to his father for his service in the Revolutionary War.
James and Rosanna are first listed in the 1820 census records of Grayson County. The census seems to include the entire family including Vincent Bobbitt brother of James.James Bobbitt: 1 male under 10 (1810-1820) William Bobbitt born in 1810 1 male under 10 (1810-1820) Lacy Bobbitt born 1815 1 male 16 - 26 (1794-1804) John Bobbitt born 1800 1 male 26 - 45 (1775-1794) Vincent Bobbitt (brother) 1 male over 45 (....- 1775) James Bobbitt born 1768 1 female under 10 (1810-1820) Ann Bobbitt born 1812 1 female under 10 (1810-1820) Celestia Bobbitt born 1819 1 female 10 - 16 (1804-1810) Jane Bobbitt born 1805 1 female 10 - 16 (1804-1810) Acenah Bobbitt born 1807 1 female 16 - 26 (1794-1804) Elizabeth Bobbitt born 1801 1 female 16 - 26 (1794-1804) Nancy Bobbitt born 1803 1 female 26 - 45 (1775-1794) Rosanna Bobbitt born 1775
This I feel is the complete family despite two older women who appear in the 1830 census. James was listed as head of household in 1794 but it was probably his fathers household.
Lacy Bobbitt brother of James and a cousin to Rosanna was a favorite with this family. He died in the service of the War of 1812 and James named his son born in 1815 after Lacy Bobbitt his brother.