Oregon Bobbitt was the sixth son, and the tenth child of John and Permelia (Hill) Bobbitt. Oregon Bobbitt was born in Amherst County, Virginia, on October 5, 1817. He was the last child to be born in Amherst County. Soon after his birth, the family moved to Rockbridge County. They lived near the village of Brownsville until 1827. In 1827 the family moved to Monroe County and lived near James Hill Junior, a brother of Permelia Bobbitt.
Oregon Bobbitt married Lucy Ann Hill, his first cousin once removed. She was the daughter of Francis and Emoline Hill. Francis Hill was a son of James Hill Junior, who was a brother of Permelia Hill, the mother of Oregon Bobbitt. Oregon and Lucy Ann were married in Monroe County on December 22, 1842. William Ellis was the bondsman, and Reverend James Reniley performed the marriage. The marriage is recorded in the county records.
Oregon Bobbitt and Lucy Ann (Hill) Bobbitt had five children:
James Hill Bobbitt born October 8, 1843
George Washington Bobbitt born September 9, 1845
Francis Napoleon Bobbitt born May 21, 1848
Emily Jane Bobbitt born February 21, 1851
Lewis Samuel Miller Bobbitt born July 22, 1853
Emily Jane and Lewis Samuel Bobbitt both died young. The family was listed in the 1850 census records of Greenbrier County. They were counted as family # 408, on November 2, 1850.
Oregon Bobbitt 33 (1817) Virginia
Lucy Ann (Hill) Bobbitt 32 (1818) Virginia
James H. Bobbitt 6 (1844) Virginia
George W. Bobbitt 4 (1846) Virginia
Napoleon Bobbitt 2 (1848) Virginia
Lucy Ann Bobbitt, wife of Oregon, died in 1853, during or shortly after the birth of their son, Samuel Bobbitt.
Early in 1854, Oregon Bobbitt married Malinda Jane Burdette, his sister-in-law, the daughter of Isham and Nancy Burdette of Monroe County. Malinda was a sister of Elizabeth Burdette, the wife of Gibson Bobbitt. Gibson Bobbitt was an older brother of Oregon Bobbitt.
Tilman Bobbitt, a brother of Oregon, married Jane Hill, a daughter of James Hill Junior and Elizabeth (Lively) Bobbitt. Lucy Ann Hill was a granddaughter of James Hill Junior.