The earliest Webb ancestor on the family tree is William Crittenden Webb, born in 1732. William married Jane Vivian, born in 1740. This generation of the family lived their entire lives in Virginia. It was the next generation, some of William and Jane's sons who brought the family into Kentucky. John Vivian Webb, born on July 11, 1765 in Orange County, Virginia. John Vivian married Lucy Woodward, born in 1764 in Orange County, Virginia. He and his brothers moved to Scott County, Kentucky in the late 1700s and quickly gathered up a large amount of land in the county. John stayed in Scott County were he raised his family and grew to be a prominent landholder. Two of his brothers did not stay though. Francis "Frank" Webb moved to St. Charles Parrish, Louisiana where he owned a plantation outside of New Orleans orginially known as Killone. Another of the brothers, Garland, moved to Mississippi where he also maintained a plantation.
The Webb line continues with Mitchum Boswell Webb, born in Scott County, Kentucky on September 5, 1802 to John and Lucy Webb. Mitchum married Susan Holmes on February 6, 1826 in Scott County, Kentucky. The couple had two daughters, Mary Boswell and Bettie Chinn. When Susan's father Robert passed away from cholera in 1833, Mitchum and Susan inherited Robert's estate, known as Elmwood; they moved into the house, even though they had just recently built a house of their own. It seems that Mitchum made a good living for himself, and when older daughter Mary married Reuben Flournoy Ford in 1843, their wedding present was a house built for them by her parents. Mary would later inherit Elmwood, and become the third generation to live in the home.
Younger daughter Bettie married John Allen Higgins, of a prominent Lexington family. John was a planter and owned lands in Arkansas and Lexington. He, Bettie, and their children split time between their homes in Arkansas and those in Lexington. It is through Bettie and John that the direct line continues as they were the parents of Alline Higgins Headley Rogers, the grandparents of Elisabeth Headley Garr and Frances Headley Carruth, and the great-grandparents of Elisabeth Garr Lawrence, Charlotte Garr Schubert, Frances Carruth Kerr, and Allen Higgins Carruth.