Stewart was born at "Tobacco Stick" (now Madison) in Dorchester County, Maryland, and attended the local school. He went on to study law in Baltimore, Maryland, was admitted to the bar in 1829, and commenced practice in Cambridge, Maryland. In addition to law, Stewart also engaged in the building of ships and houses.
Stewart was born at "Tobacco Stick" (now Madison) in Dorchester County, Maryland, and attended the local school. He later studied law in Baltimore, Maryland, received his legal license in 1829, and began practicing law in Cambridge, Maryland. In addition to law, Stewart also engaged in shipbuilding and house construction.