Frederick Douglass escaped slavery on September 3, 1838, by traveling from Baltimore to the North disguised as a sailor and using borrowed free papers to pass as a free Black seaman. The journey took about 24 hours and ended with his arrival in New York City, where he declared himself free.

Quick Scoop

  • Douglass was enslaved in Maryland and had been working in Baltimoreā€™s shipyards, where he learned seafaring language, dress, and mannerisms that later helped his disguise as a sailor.
  • A free Black woman he loved, Anna Murray, helped fund and plan his escape, including buying his train ticket and supporting him with money and clothing.
  • On the morning of September 3, 1838, he put on a sailorā€™s outfit (red shirt, tarpaulin hat, black neckerchief) and boarded a northbound train out of Baltimore using travel papers borrowed from a free Black sailor.
  • When a conductor demanded his documents, he briefly showed the borrowed seamanā€™s papers, which were not a perfect match to his appearance, but the conductor accepted them without close inspection.
  • Douglass then transferred between trains and boats through slave-catching territory, passing through Havre de Grace, Delaware, and Pennsylvania, constantly at risk of being recognized and seized.
  • After reaching Philadelphia, a free city, he continued on to New York, arriving the next day and later describing that moment as when he first felt truly free on ā€œfree soil.ā€
  • Soon after, Anna Murray joined him, and the two settled in New Bedford, Massachusetts, where he took the surname ā€œDouglassā€ and began his public work as an abolitionist and writer.

In his later autobiographies, Douglass emphasized that he kept some details vague for years to avoid endangering the people and methods that had helped him escape, a reminder of how dangerous such flights from slavery remained even in the North.

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