Olive Crafts (maiden name: Day) was born on August 28, 1821, in West Springfield, Massachusetts, to Alexander and Phebe Day. She married Chester Crafts in West Springfield on May 30, 1843, and they had at least five children: Edward, born around 1844; Alexander, born around 1846; Howard, born around 1849; Judson, born around 1850; and Linus, born around 1852. They settled in Holyoke, Massachusetts, and her husband worked as an “inn holder.”
By 1850, they owned $9,204 of real estate. A decade later, he owned $10,000 of real estate and $10,000 of personal property. By 1870, their wealth had grown to $32,000 of real estate and $12,000 of personal property. Her husband died of consumption in Holyoke on June 10, 1871. She remained in Holyoke for the rest of her life, and by the early 1900s, residents referred to her as “Holyoke’s Grand Old Lady.” She died there in February 1914 after fracturing her leg in a fall.