James Bobbitt was born on April 27, 1772. He was the second son of Captain William and Nancy (McKenzie) Bobbitt. James was born in what was at that time Montgomery County Virginia. Part of Montgomery County was taken to form Grayson County Virginia. James was named for his grandfather, James Bobbitt of Pittsylvania County Virginia.
James Bobbitt married Rebecca Day in Grayson County Virginia on October 14, 1796. Rebecca Day was a daughter of Joseph and Rebecca Day of Bute County North Carolina.
James Bobbitt was listed in the tax lists of Grayson County from 1796 until 1803. In 1803 James and Rebecca moved to Pulaski County Kentucky. The first record of James Bobbitt in Kentucky was recorded in Deed Book 2, pages 336 - 337 in Pulaski County.
"I James Reese of the county of Pulaski and State of Kentucky, hath sold a tract of land on the waters of Flat Lick, containing 170 acres, for 1500 dollars, to be paid within the space of five years. in -the presence of David Hardesty, and Peter Lee. December 4, 1804."
The next record of interest was an indenture recorded in Deed Book 3, pages 367-368 of Pulaski County.
"Know ye, that we James Bobbitt and Janney Richardson, of the county of Pulaski .... have appointed our trusty friend, and 1 awful attorney, William Morgan, of the same county and state, to represent us in the singular legacy that is bequeathed to us by our father, William Bobbitt, deceased, of Grayson County Virginia."
August 24, 1818 James Bobbitt
Jane (Bobbitt) Richardson
The deed proves that James Bobbitt was the son of William Bobbitt of Grayson County. His sister, Jane Bobbitt, married a Richardson and moved to Pulaski County.
When James Bobbitt and his family arrived in Pulaski County Kentucky, his uncle, James Bobbitt was living there. Uncle James Bobbitt had received a land grant for his service in the war of the American Revolution. It was undoubtedly the influence of Uncle James Bobbitt that caused many of the Bobbitt families of Grayson County to migrate to Pulaski County Kentucky. The land was supposed to be more fertile for farming. James and Rebecca made their home with the family of Uncle James Bobbitt.