Shakespeare’s works are famous for portraying cross-dressing, particularly for the purpose of dealing dastardly and playing tricks on people. However, his fictions are nothing compared to the realities during slavery in America, where several enslaved people completed incredible escapes by disguising themselves as white.

The most famous perhaps is that of Ellen and William Craft, an enslaved married couple from Macon, Georgia, who decided to take a chance on Ellen’s half-white and very fair skin to dress her up as an affluent young white man and make a five-day journey to the North. William would come along, pretending to be Ellen’s slave.

Recounted in breath-holding detail in their memoir, Running a Thousand Miles for Freedom, it’s a story worthy of remembering as Black History Month draws to a close.

After deciding to escape, William, who had some considerable talent as a cabinet maker, began to buy men’s clothes for Ellen including a top hat, green spectacles, and a long jacket. Neither spouse could read, and considering the need to sign agreements for payments, hotel guestbooks, and passenger logs, they decided to feign illness in her right arm by bandaging it, hanging it in a sling, and claiming they were visiting a specialist in Philadelphia.

The great escape

As the pair possessed unique skillsets among enslaved peoples, their circumstances allowed them to obtain written permission to leave their enslavers’ property for the purpose of errands.

A series of close encounters followed in the days after their December 21, 1848 escape, including on their first train ride to Savannah, Georgia when the passenger Ellen was seated next to, to her horror, was a dear friend of her previous enslaver. Already bandaged, Ellen pretended to be deaf the whole way.

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Despite enduring some unsavory language at the hand of a steamboat worker and by an army captain, by the time they reached Charleston, South Carolina, they were able to stay at the finest hotel and restaurant, where the staff were all too eager to care for the “invalid” young man.

They then took a steamboat to Wilmington, North Carolina, a train to Richmond, Virginia, and another steamboat to Maryland. With one last voyage by train, the two discovered they weren’t allowing enslaved people traveling on trains to the North, for fear they could be escaping.

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Ellen was pressed hard for proper documentation to prove that William belonged to her, when a sympathetic conductor, once again falling for the bandaged arm, skirted them around the restrictions and boarded them to Philadelphia.

On Christmas Day, the Crafts stepped off the train into Philadelphia. Ellen cried out: “Thank God, William, we’re safe!”

Keeping a high profile

They quickly settled among abolitionist communities in Boston, found work, learned to read and write, and became outspoken critics of slavery. Abolitionists such as William Lloyd Garrison and William Wells Brown encouraged them to recount their escape in public lectures to the abolitionist circles of New England.

After Congress passed the Fugitive Slave Act of 1850, the pair decided it was no longer safe for them in Boston, as two bounty hunters had been alerted of their whereabouts. The two left American shores for England, where they raised five children in Hammersmith, and continued their ample campaigning on behalf of the enslaved back home, including through the publishing of William’s book.

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The proslavery press in the U.S. had suggested the Crafts regretted their flight to England, and in 1852 Ellen Craft published the following, which was widely circulated in the abolitionist press in both the United Kingdom and the U.S:

“So I write these few lines merely to say that the statement is entirely unfounded, for I have never had the slightest inclination whatever of returning to bondage; and God forbid that I should ever be so false to liberty as to prefer slavery in its stead. In fact, since my escape from slavery, I have gotten much better in every respect than I could have possibly anticipated. Though, had it been to the contrary, my feelings in regard to this would have been just the same, for I had much rather starve in England, a free woman, than be a slave for the best man that ever breathed upon the American continent.”

The Crafts returned to Georgia after the American Civil War in 1868, and began the Woodville Co-operative Farm School for freemen’s children.

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