Winfield S. Libby was born around 1838 in Maine to Hiram and Naomi Libby. His father was a farmer who owned $1,000 of real estate and $500 of personal property by 1860. The family lived in Carthage, Maine, until the 1850s, when they moved to Dixfield, Maine. By 1860, he was working as a farm laborer. He married Sarah Frost, and their son Lester was born around 1870. They lived in Weld, Maine, and he earned a living as a farmer. By 1870, he owned $1,200 of real estate and $575 of personal property. He died in Weld on March 31, 1876.