Stories About Daring And Elaborate Escapes Throughout History

List Rules
Vote up the plans that took the most brains and guts to pull off.

Stories about people escaping tough situations can be inspiring, especially when the escapee is innocent and truly deserves freedom. Sometimes, the most interesting getaway stories are about how people escaped from prison, which doesn't make them heroes. But other escapees are more heroic, admired for their courage as they broke free from inhumane conditions.

Real-life escape artists from history had a lot of brains and gumption. Vote up the stories about escapes that required serious guts, even if the escapees weren't inspiring or courageous.


  • 1
    154 VOTES

    Robert Smalls Escaped Enslavement By Taking A Confederate Steamer And Sailing Toward A Union Blockade

    Robert Smalls eventually became a member of the US House of Representatives in the 1880s, but long before then, he was born into enslavement in South Carolina. As a child, Smalls seemed to be favored over other enslaved children by the owner of the city home where he and his mother lived and worked. Smalls's mother worried that because of this treatment, her son might not understand the plight of the other enslaved people around him. So she sent him to observe other enslaved people being whipped, and later, to work in another city.

    Smalls eventually became an accomplished sailor and married a woman who was enslaved as well. He wanted to purchase freedom for his wife and their children from their owner but did not have the money to do so. An opportunity to escape came in 1862 during the Civil War when he and other enslaved people were working aboard the CSS Planter, a Confederate ship based in Charleston. On the night of May 12, 1862, the ship's three white officers - Capt. C.J. Relyea, pilot Samuel H. Smith, and engineer Zerich Pitcher - decided to disembark (possibly to visit family). They trusted the Black crew aboard the Planter so much that they left the ship in their care.

    Smalls, who had been waiting for an opportunity like this, took the helm of the heavily armored ship and moved it out of the dock. After picking up his wife, children, and eight other enslaved people at a nearby wharf, he went down the Charleston River. Smalls knew the proper Navy signals and was able to pass for the real captain in the dark by wearing Relyea's straw hat. He steered the ship toward a Union blockade, and once he was out of Confederate firing range, lowered the Confederate flag and raised a white color of surrender. 

    He went on to serve in the Union Navy, buy his former master's house, and serve as a US congressman.

    154 votes
  • Kazimierz Piechowski Snuck Out Of Auschwitz By Taking A Car And An SS Uniform
    Photo: Unknown / Wikimedia Commons / Public domain
    2
    172 VOTES

    Kazimierz Piechowski Snuck Out Of Auschwitz By Taking A Car And An SS Uniform

    Kazimierz Piechowski had a happy childhood in the town of Tczew in Poland and later joined the Polish Scouts. When the Germans entered Poland in 1939, they began to kill the Scouts on charges of anti-nationalism. Piechowski fled but was detained at the Hungarian border and taken to the Auschwitz concentration camp. 

    Piechowski later recalled that the Germans beat inmates with truncheons to solve the problem of overcrowding, or simply shot them. But soon he and a friend, along with two other prisoners, came up with an escape plan.

    Piechowski's friend was a mechanic at the camp and could arrange for a car, while Piechowski had access to German soldiers' uniforms in a storage area. After first using a rubbish cart to walk to the gate, the four Auschwitz detainees made their way to the storage rooms. There, they dressed in German uniforms and took a Steyr 220 car that belonged to the camp's commander, Rudolph Höss. 

    When the guards saw the car, they were confused, especially when one of the men inside, dressed in the uniform of a second lieutenant, began to yell at them. This was Piechowski, and the guards opened the gates, letting the four men go.

    They drove through the forest to keep out of sight, then walked on foot to freedom.

    After returning to Poland, Piechowski joined the Polish army and fought the Germans during WWII. He lived until age 98

    172 votes
  • 3
    55 VOTES

    Three Men Escaped Alcatraz Using A Boat Made Out Of Raincoats

    In 1962, three inmates escaped from Alcatraz prison. Brothers Clarence and John Anglin, with Frank Morris and another inmate who was left behind, developed a plan to escape the island prison via the water. 

    The men first loosened the air vents in their cells by drilling small holes around them so they could eventually remove an entire section of the wall. Behind their rooms was an unguarded utility corridor they used to go up to the roof of their cell block. They set up a workshop, and painstakingly turned 50 raincoats and other materials (pilfered or donated) into a raft and life preservers. 

    On the day of their escape, June 11, 1962, they climbed up the roof, shimmied down, and set the raft in the water. In the morning, jail authorities discovered they had placed plaster dummies in their beds, fooling the guards who checked their cells.

    When the escape was discovered, the FBI was called in. FBI authorities said they don't know if the trio made it out alive or not, and closed the case in 1979. 

    55 votes
  • Ellen And William Craft Dressed In Disguises And Bumped Elbows With White Elites On Their Journey North
    Photo: Unknown / Wikimedia Commons / Public domain
    4
    88 VOTES

    Ellen And William Craft Dressed In Disguises And Bumped Elbows With White Elites On Their Journey North

    Ellen Craft, an enslaved woman in Georgia, was the child of her master and was so light-skinned, she could pass for white. When she met William Craft, an enslaved man, the two fell in love and eventually married. But anxiety set in because both had been separated during their lives from family members, and didn't want the same to happen to them.

    So in 1848, the couple planned a daring escape North. Ellen would dress as William's white master, with her arm in a sling and bandage wrapped around her face, and wearing pants she sewed herself. William would travel as his master's loyal servant. With a little money, the two set off, facing some narrow escapes. They boarded a train in Georgia from Macon to Savannah, then a steamer from Charleston, SC, to North Carolina. From there they boarded another steamer to Philadelphia. 

    Two years later, when hunters came looking for them, the couple fled to England, returning 20 years later to start a school in Georgia for newly freed Black people.

    88 votes
  • Frederick Douglass Fled On A Train With Papers Of A Man Who Looked Nothing Like Him
    Photo: Unknown / Wikimedia Commons / Public domain

    Frederick Douglass, born around 1818 into enslavement in Maryland, learned how to read and write and longed to be free. In 1838, after many attempts at escaping to the North, he finally succeeded.     

    Douglass planned to escape by train, posing as a free Black man with the proper documentation. At the time, enslaved people trying to escape would often borrow the papers of another free Black person and travel via rail. Douglass learned that Black sailors traveling on trains were not scrutinized as deeply as other Black men, so he decided to pose as a sailor, which wasn't difficult because he had previously worked at shipyards.

    He didn't look anything like the sailor friend whose papers he borrowed but figured that dressing and talking like a sailor would work to his advantage. Douglass later wrote in his autobiography:

    My knowledge of ships and sailor’s talk came much to my assistance, for I knew a ship from stem to stern, and from keelson to cross-trees, and could talk sailor like an "old salt."

    He boarded the train from Baltimore to Philadelphia and arrived in New York despite a few close calls. He went on to become one of the biggest leaders in the abolitionist movement.

    103 votes
  • 6
    79 VOTES

    Ed Ray And 26 Kids Had To Dig Their Way Out After Being Buried In A Truck

    In July 1976, in the small farming town of Chowchilla, CA, bus driver Ed Ray and 26 children, ages 5 to 14, were kidnapped by three masked, armed men.

    The men abandoned the bus, then transported their captives in vans to a quarry 100 miles away in Livermore, CA. They forced the prisoners into a trailer truck buried in the ground along with a few mattresses, snacks, water, and holes for toilets.

    A ransom demand was made for $5 million. Meanwhile, Ray and two of the older students, 14-year-old Mike Marshall and 10-year-old Robert Gonzales, tried to break their way out.

    It was stiflingly hot, and Ray kept dousing them with water to keep cool. They pushed on the ceiling of the truck until they saw starlight. Ray and the students climbed out and made their way toward help.

    The three kidnappers turned out to be local rich kids who wanted the ransom money to buy themselves Ferraris. They were caught and prosecuted. Ray, declared a hero, lived a simple life as a bus driver and farmer until he passed in 2012 at age 91.

    79 votes