Caleb Bobbitt was a son of Captain William and Nancy (McKenzie) Bobbitt. Caleb was born on January 5, 1770 in Montgomery County Virginia in that section that later became Grayson County Virginia.
Caleb Bobbitt married Nancy Blair, daughter of Thomas Blair, in Grayson County Virginia on April 3, 1795. Nancy (Blair) Bobbitt was born in 1778 and died in 1876 at the age of 98. She was the sister of John Blair who served in the Virginia State Legislature from Grayson County. Nancy Bobbitt was a remarkable woman who tells about herself and her family in the "Greenberry Bobbitt Letters". These were letters that Nancy wrote to her son Greenberry, who remained in Grayson County when the family moved to Pulaski County Kentucky.
The family of Caleb and Nancy Bobbitt was first recorded in the census records of 1820 in Grayson County Virginia. In 1827 Caleb and Nancy moved to Pulaski County Kentucky where Caleb died in 1830 before the census records were made in that year. Nancy is listed in Pulaski County in the census records of 1830 along with her son Thomas and Hannah Gilmore. In 1831 Thomas Bobbitt married Hannah Gilmore.
The children of Caleb and Nancy (Blair) Bobbitt were:Thomas Bobbitt born 1796 Greenberry Bobbitt born 1798 Caleb Bobbitt Junior born 1804 Mary (Polly) Bobbitt born 1805 William Bobbitt born 1810 Alexander Bobbitt born 1812 Nancy Bobbitt born 1815 Rebecca Bobbitt born 1818 Sarah Bobbitt born 1821
Caleb Bobbitt Jr., died when he was 13 years old. Nancy Bobbitt died when she was about 16 years old. The rest of the children all married and reared families of their own.Thomas Bobbitt m. Hannah Gilmore 1831 Pulaski Co. Ky. Greenberry Bobbitt m. Lydia Jennings 1825 Grayson Co. Va. Mary Bobbitt m. Johnson Doolin 1830 Pulaski Co. Ky. William Bobbitt m. Cecelia Jennings 1836 Grayson Co. Va. Alexander Bobbitt m. Saphrona Coffey 1836 Wayne Co. Ky. Rebecca Bobbitt m. Enoch Liggett 1840 Pulaski Co. Ky. Sarah Bobbitt m. Jacob Thomas 1841 Pulaski Co. Ky.
Only William and Cecelia lived out their lives in Kentucky. The other members of the family migrated to Missouri and other parts of the country.