Pathways to Freedom: Maryland and the Underground Railroad
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Did enslaved people ever wear disguises?

Enslaved people sometimes wore disguises to avoid being recognized and returned to slavery. The story of Ann Maria Weems is an interesting one. She belonged to a trader who lived in Montgomery County. Three of her brothers had been sold south. Her mother and one of her sisters had been purchased for freedom. Ann's owner had been offered $700 for her freedom, but he had refused. It was clear that her only way to obtain freedom was the Underground Railroad.

Henry Box Brown
Henry “Box” Brown “mailed” himself to freedom, traveling to Philadelphia in a wooden crate
disguised as “cargo.”

A white doctor, who was a conductor for the Underground Railroad, picked her up in his carriage. Ann was disguised as a young boy and given the name "Joe Wright." She was to act as a coachman who assisted with the carriage and horses. The doctor and "Joe" had to travel all the way through Maryland. In those days, that meant that they had to spend at least one night, because of the length of the journey. The doctor decided to stop at the house of some old acquaintances of his. They were slave owners. He pretended that "Joe" was his slave. He also pretended that he had dizzy spells and therefore needed "Joe" to sleep in his own bedroom with him. The dangerous trick worked, and the next day the pair proceeded on to Philadelphia. After two or three days there, Ann Maria Weems went on to New York and then, eventually, to the Buxton settlement in Canada.

What happened if an enslaved people was caught while he or she was trying to escape?

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