Henry was the son of Polly Jackson Freeman but his father is unknown. His 2nd wife was Olive Prutt. They married ca. Feb. 28, 1856. In 1840, when Henry was 23 years old, he was involved in the abduction of Angeline Palmer of Belchertown, MA. The Wood Museum of Springfield (MA) History has a drawing of Henry, done in his later years. He is described as being a "truckman" from Amherst, MA.