Madison Hemings worked as a carpenter and farmer after obtaining freedom from slavery at Monticello. As a teenager he had been apprenticed to his uncle John Hemmings, a skilled joiner who trained members of the extended Hemings family. Thomas Jefferson's will freed Madison in 1826. Special legislative permission allowed him to remain in Virginia despite the state's law requiring most newly freed people to leave.

He and his brother Eston purchased a lot in Charlottesville and built a house where their mother, Sally Hemings, also lived. Madison supported himself through carpentry during the following decade. He married Mary Hughes McCoy in 1831. After his mother's death, he moved with his family to southern Ohio in 1836. There he worked at his trade, farmed, and raised his children, remaining identified with the area's African American community. He established a free household in a state that still imposed legal and social barriers on Black residents.

In 1873 the Pike County Republican published his recollections, recorded by editor Samuel Wetmore. Hemings described his training, emancipation, marriage, and migration, and identified Jefferson as his father and the father of his siblings. The account preserves his own understanding of his family's experience and has become important evidence in studying Monticello's enslaved community. It should not obscure his decades of independent adult work: he was a tradesman and parent, with a life beyond his connection to Jefferson.