Ira Sayles was born in Burriville, Rhode Island in 1817, and moved with his parents, Christopher and Sarah (King) Sayles to Tioga County, Pennsylvania around 1825. He was a self-educated man when enrolling in Alfred Academy, Alfred, New York, in the fall of 1839; he met while there Serena Crandall White, the daughter of prominent Allegany County citizens Samuel S. and Nancy (Teater) White. They married in 1845.
Three of their four children survived to adulthood, but only one married and had children:
In the 1870′s Clifton Duvall Sayles was denied the first love of his life, Rebecca Eulalia “Lilly” Dodson, because he was a Yankee living in Mecklenburg County, Virginia. Lilly had lost brother Green and uncle Benjamin Franklin Dodson during the Seige of Petersburg in 1864. Feelings ran high among the family. Clifton eventually married Anna McCullough, daughter of other northern colonists. They had several children before Anna died in 1899.
In January of 1901, Lilly and Clifton finally married. Miraculously a daughter was born to this middle-aged couple December of that very year: Anna Florette Sayles.