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Ingenious Stories of Daring Slave Escapes That Will Make You Proud to Be Black

As we inch toward Juneteenth, the holiday commemorating the end of slavery in the United States, it is important to remember that long before African Americans were granted their freedom in law, extremely brave and intelligent enslaved people were leading their own revolutions and freeing themselves from the shackles placed around their feet.

Their stories are not just moments in history, but important reminders of the horrific struggles African Americans had to endure for the liberty we enjoy today. From leading the way through treacherous swamps to disguising themselves as White people, these are 13 heroes of history we are remembering this Juneteenth.

Harriet Tubman

Portrait of activist and abolitionist Harriet Tubman, half length, 1895. Note: Image has been digitally colorized using a modern process. Colors may not be period-accurate. From the Gado Modern Color series. (Photo by Smith Collection/Gado/Getty Images)

Harriet Tubman pulled off what seemed like an impossible feat: She escaped slavery near the end of 1849 after her slave master died. Fearing she would be sold to a new master and separated from her family, Tubman fled Maryland through swampy marshlands until she reached Philadelphia, Pennsylvania, where she became a free woman, according to the National Park Service.

While in flight, the abolitionist adopted many ingenious disguises. According to the American Battlefield Trust, she would dress as a man and carry two chickens under her arms, pretending to be a local farmhand at work and passing right under the noses of slave catchers. Known to be illiterate, she would read newspapers so anyone looking for her would not suspect the short gentleman reading in the corner. She also helped 70 people escape slavery through the Underground Railroad once she had established her freedom.

William and Ellen Craft

William and Ellen Craft, 1872. Creator: Unknown. (Photo by Heritage Art/Heritage Images via Getty Images)

William and Ellen Craft not only freed themselves from slavery, but they also left America entirely and sailed across the Atlantic to the United Kingdom. According to the British historical site English Heritage, in 1848, Ellen Craft, a biracial woman pale enough to pass as White, disguised herself as a disabled White man heading north from Georgia to Pennsylvania for medical care. Besides Ellen, her husband William played the role of her slave.

However, they only lived in Pennsylvania for two years before the Fugitive Slave Act was passed, which gave their former slave master the right to put a bounty on the Crafts’ heads for capture. With the help of abolitionists, the couple fled north to Nova Scotia before taking a final ship to Liverpool, England, according to Historic UK. They settled down in London until 1865, when they returned to the States.

Robert Smalls

Screenshot: TikTok

A highly intelligent sailor, Robert Smalls escaped thanks to his knowledge of boats and the arrogance of the White ship officers, who left him alone on board the Planter steamship while they took a night off. According to PBS, Smalls kept his plan to himself until the perfect moment to escape arrived. Then he confided in the other slaves on the deck of his mission to set sail to freedom.

Guiding his crew, Smalls ordered them to wave Confederate flags to disguise the ship while he flashed navy signals that would help them slip past other boats and docks without raising attention. It would only be when the Planter had made it past enemy lines that an alarm was raised, but by then it was too late. Smalls successfully sailed his family and his crew to safety and freedom, per PBS.

Henry “Box” Brown

Henry ‘Box’ Brown emerges from a three-foot box after mailing himself to the Anti-Slavery office in Philadelphia to escape from slavery in Richmond, Virginia, 24th March 1849. After his wife’s owner sold her and their children, Brown, with the help of two allies, sent himself on the 27-hour, 350-mile journey using the Adams’ Express, a private firm in Richmond. Witnessing his arrival are prominent abolitionists (left to right) Lewis Thompson (1807 – 1866), James Miller McKim (1810 – 1874), William Still (1821 – 1902) and Charles Dexter Cleveland (1802 – 1869). Lithograph, ‘The Resurrection of Henry Box Brown at Philadelphia’, by Peter Kramer, circa 1851. Printed by Thomas Sinclair, Philadelphia. (Photo by MPI/Getty Images)

Henry Brown had an extremely uncomfortable journey to free himself from slavery. He was fleeing from his plantation in Richmond, Virginia, and asked James Caesar Anthony Smith, a free Black man, to help him. Smith got in contact with Samuel Alexander Smith, a White man willing to help slaves escape for a price, according to Encyclopedia Virginia.

Together, they devised a plan for Brown to be shipped in a box to Pennsylvania. Per Encyclopedia Virginia, the pair created a three-foot-long, two-and-a-half-foot-deep box for Brown to be packaged in and delivered to James Miller McKim, a leader of the abolitionist movement in Philadelphia. It was a rough, 26-hour journey for Brown, who almost died, but thankfully made it to Pennsylvania alive and, most importantly, free.

Anna Maria Weems

Screenshot: TikTok

Anna Maria Weems was only 15 years old when she made the journey from the United States to Canada in 1855. Separated from her family, Weems ran away from her slave master’s home in Rockville, Maryland, to Washington. She found refuge with abolitionist Jacob Bigelow, who hid her for six weeks until Dr. Ellwood Harvey, another abolitionist, would help Weems and Bigelow on their journey to Canada, according to the publication World History.

To remain undetected, Weems acted as a male carriage driver under the alias “Joe Wright” and managed to slither under the nose of bounty hunters searching for her. She secured her freedom in Pennsylvania, but continued up north to New York and eventually crossed the border into Ontario, Canada, reuniting with her family in December 1855, per World History.

Lear Green

Screenshot: TikTok

Similar to Henry “Box” Brown’s escape, Lear Green had to survive hours in an old sailor’s chest to become a freewoman. According to the African news publication Face2Face Africa, the plan was devised by Green’s fiancé and her mother-in-law, both free Black people. The chest was secured with rope and placed on a steamship from Baltimore, Maryland, to Philadelphia, Pennsylvania.

Green’s mother-in-law was also on the boat, checking on Green every once in a while and loosening the chest so Green could breathe. It was 18 hours before Green made it to Philadelphia, where she met with abolitionist William Still, who took her to Canada, per Face2Face Africa.

Frederick Douglass

circa 1855: American abolitionist, Frederick Douglass, agent of the Massachusetts Anti-Slavery Society and US Minister to Haiti in 1889, (Frederick Augustus Washington Bailey) (1817 – 1895). Formerly enslaved he became the first Black man to be received at the White House, by President Abraham Lincoln. (Photo by Library Of Congress/Getty Images)

Having been awarded the privilege of earning wages and living independently by his slave master, Douglass decided to make his dash for freedom when his master warned him that the small freedom he had would be taken from him. According to the Gilder Lehrman Institute of American History, Douglass secured the papers of a free Black sailor through a free woman, Anna Murray, who would go on to become his wife.

With these papers, Douglass boarded a train from Baltimore to New York and finally became a free man. Once he arrived in the Big Apple, Douglass, whose name at the time was Frederick Bailey, changed his last name to conceal his identity and hidefrom potential fugitive slave hunters.

John Andrew Jackson

Screenshot: YouTube/Saint Louis In Tune

According to Smithsonian Magazine, John Andrew Jackson was the real-life slave who inspired the novel “Uncle Tom’s Cabin.” On Christmas Day of 1846, Jackson ran away from his South Carolina plantation on horseback and settled on the docks of Charleston, hiding between bales of cotton before boarding a ship headed to Boston, Massachusetts.

However, Boston wasn’t Jackson’s final stop. Like many at the time, Jackson continued to Canada, and on his journey to the country, he stayed with abolitionists. One of them was Harriet Beecher Stowe, the author of “Uncle Tom’s Cabin,” who took inspiration from his journey for her novel. After Jackson arrived in New Brunswick, Canada, he set sail to Liverpool, England, where he lived until 1865, per Smithsonian Magazine.

Osman

Screenshot: TikTok

Though there are no records of how Osman escaped, what’s understood is that Osman, along with other runaways, made their own civilizations and islands in the Great Dismal Swamps of Virginia and North Carolina. While some of these slaves would move on from the swamps, many stayed, protecting the swamp protected the swamp from slave catchers.

According to Encyclopedia Virginia, David Hunter Strother, a writer for Harper’s New Monthly magazine in 1856, had an eyewitness account of Osman and sketched him as a man with an overgrown beard and hair with a shotgun in hand, ready to fight against anyone who attempted to disrupt his swamp community.

Jane Johnson

Screenshot: TikTok

Jane Johnson emancipated herself and her children from slavery while she journeyed with her slave master, John H. Wheeler, through Philadelphia to South America. According to the historical site Quakers and Slavery, it was while they made a pit stop in Pennsylvania that Johnson was able to get in contact with free Black men and women, who sent a message on her behalf to the Pennsylvania Anti-Slavery Society to free Johnson.

However, even though Johnson was declared a freewoman under Philadelphia law, Wheeler protested this, and she had to testify in court that she had left Wheeler of her own volition. This meant risking the court putting her back in the hands of her former master, but Johnson won her case and remained a free woman, per Quakers and Slavery.

Clarissa Davis

The Runaway. Wooden engraving used on handbills offering rewards to those who found fugitive slaves, 1837, United States, Washington. Library of Congress, . (Photo by: Photo12/Universal Images Group via Getty Images)

Clarissa Davis had been on the run with her brothers when she tried to make her escape, but fell behind and had to seek refuge in a secluded coop, waiting until she could make another attempt. That moment came when she heard of a ship leaving Virginia and heading towards Pennsylvania, according to the New Bedford Historical Society. It was two-and-a-half months before she would get that moment.

Clad in male clothing, Davis dashed onto the steamship and was hidden in a box by William Bagnal, a steward on the ship, who was for the abolitionist movement. In Philadelphia, Davis changed her name to Mary D. Armstead and helped Davis reunite with her brothers in New Bedford, Massachusetts, per the New Bedford Historical Society.

Shepard Mallory, Frank Baker and James Townsend

Color illustration showing Fort Monroe, Old Point Comfort and the Hygeia Hotel, in Virginia, 1861. Illustration by E. Sachse & Company. (Photo by Buyenlarge/Getty Images)

In 1861, Virginia seceded from the United States to join the Confederacy and considered itself a sovereign nation, foreign to the United States. This would backfire against them when slaves Shepard Mallory, Frank Baker and James Townsend, belonging to Confederate Colonel Charles K. Mallory, fled from inland Virginia to Fort Monroe, an island military base in Hampton, owned by the United States.

According to the National Park Service, the three men rowed a boat to the U.S. territory and asked for asylum from U.S. Major General Benjamin F. Butler, who granted the slaves their request. When the Confederate Army demanded that the men be returned on the grounds of the Fugitive Slave Act, their request was refused because American laws cannot be used against foreign countries, as Virginia considered itself to be.

Wesley Harris

Slaves revolt against their slavers aboard a slave ship. (Photo by © CORBIS/Corbis via Getty Images)

Wesley Harris made a bid for his escape when he learned he was to be sold by his owner at Christmas. According to the National Park Service, Harris, along with two more slaves, ran from Virginia up north to Maryland, where they hid in the woods before they were found, arrested and shot .

Harris had a wound in his left arm and was hemorrhaging. But using a rope secure the wound, he managed to escape from prison and meet up with a friend who would bring Harris to Gettysburg, Pennsylvania. There, he was given medical attention, clothes and a one-way ticket to Canada, per the National Park Service.

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