Frederick Douglass Escapes to Freedom (1838) On September 3, 1838, Frederick Douglass, who would become one of America’s greatest orators and abolitionists, executed a dramatic escape from slavery. Disguised in a sailor’s uniform, he traveled from Maryland to New York City—utilizing train, ferry, steamboat, and foot—to secure his freedom. This bold move set the stage for his influential work as an author, human rights leader, and the first African American to serve as U.S. Minister-Resident and