This chapter examines Douglass’s time in Baltimore between 1826 and 1838. “The nineteenth century’s black capital,” Baltimore was then home to the largest concentration of free black people in any U.S. city. Eight-year-old Frederick Bailey arrived in Baltimore in March 1826, staying with the Auld family in Fell’s Point. Five years later, he joined the Strawberry Alley black Methodist church, the oldest permanent Methodist place of worship in the city. The Methodist Church, with its important traditions of literacy and abolition, had two huge black congregations in Baltimore – Sharp Street and Bethel AME – which served as foci for literacy, oratory, and reasoning against bondage. Douglass entered black religious and educational circles fully as a teenager and, with the addition of the important neighborhood networks of Fell’s Point’s black caulkers and seamen, these associations were key ideational and material supports to his escape from slavery in 1838.