Freeman was about 24 when he left Virginia to live in Monroe, Ga. He stayed there for more than ten years before moving to Indianapolis in 1844. For five years he worked as a janitor in the church of Congregationalist preacher Henry Ward Beecher, brother of Harriet Beecher Stowe and a leader in the antislavery movement. By 1850, according to a census, Freeman was the wealthiest African American in Marion County, with a restaurant in Indianapolis and four acres of land on which he grew crops for his restaurant.
In that same year, the U.S. Congress passed the second Fugitive Slave Act, which strengthened the already existing laws regarding the return of runaway slaves who fled across state lines. In 1853 Freeman was arrested under this Act, after a Missouri man, Pleasant Ellington, claimed that Freeman was his slave and had run away in 1836, when he (Ellington) was living in Kentucky. To prove that he was free and not a slave, Freeman had to pay to have witnesses come from Georgia, Alabama, and Kentucky. Eventually he was released, but he was nearly ruined financially. With contributions from the community, which had rallied to support him, he was able to pay his debts and save some of his property.
Freeman was married to Letitia Draper; the couple had five children, Henry, John Jr., Elijah, Martha, and Harriet. At the outbreak of the Civil War, Freeman moved his family to Canada out of fear for their safety if the South won. In 1870 they returned to the United States, settling in Topeka, Kans.Died: ?