Chester Crafts was born on March 6, 1812, in West Springfield, Massachusetts. He married Martha Graves Morgan in Brattleboro, Vermont, on November 25, 1834, and their son Homer was born around 1837. His wife died in the late 1830s, and Crafts married Sarah W. Knight in West Springfield on August 12, 1840. Their daughter Sarah was born around 1842. His wife died in the early 1840s, and he married Olive Day on May 30, 1843. 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.
As a young man, Crafts worked as a hostler in West Springfield, Then, in 1837, he purchased a tavern and inn in Holyoke, Massachusetts. His inn served as the “social center of this section” of the county. It also “served as a political meeting place and [location] for red hot debates between the Whigs, Know-Nothings and representatives of other political parties.”
By 1850, Crafts owned $9,204 of real estate. A decade later, he owned $10,000 of real estate and $10,000 of personal property, and by 1870, his wealth had grown to $32,000 of real estate and $12,000 of personal property. He died of consumption in Holyoke on June 10, 1871.