Breaking Chains and Chasing Freedom: Stories of Defiance
Life as a slave in the American South was a nightmare—every move controlled, every dream crushed, and the constant fear of losing your family hanging over your head. But even in the darkest times, the hope for freedom never died. Some people found ways to fight back in little ways, slowing down work or sneaking in small acts of rebellion. Others went all in, risking everything to escape. The Underground Railroad, a secret network of safe houses and brave helpers, became a lifeline for thousands. But escaping slavery wasn’t just about the Railroad—it was about people finding the courage to take a chance on freedom, no matter how dangerous the odds.
Whether it was following the North Star, disguising themselves as someone else, or outsmarting patrols, enslaved people used every ounce of their ingenuity to make a break for it. Heroes like Harriet Tubman and the Crafts showed that bravery came in all forms, inspiring others to take their shot at freedom. These stories aren’t just about escaping—they’re about refusing to accept a life in chains and proving that even in the face of cruelty, the human spirit can’t be crushed.
Escape from Slavery
An untold number of slaves tried to escape to freedom. Only a fraction made it past a few miles from their plantation. The chances of escaping to freedom for any slave was a risky business and the punishments of being recaptured were severe. A recaptured slave could most certainly count on a beating. Sometimes they might be punished with a collar fixed to bells. The worst punishment was to be sold “down south” forever separated from friends and family. No wonder that many slaves chose not to run away. Instead, they used other ways to defy their masters.
Despite the lies the plantation owners told to justify their system, no slave actually enjoyed living a life of bondage. More than being physically cruel, slavery was psychological terrorism. Slaves were taught that they were property, not human beings.
Even the masters became victims of their own abuse, after all, slavery trained them to become emotionally crippled individuals. The whole system corrupted anyone who came in contact with it.
Slaves dealt with their situation the best way they could. Mostly they would find ways of slowing down their work without risking a lashing by the overseer. Other slaves – like resistance fighters in occupied territory – engaged in sabotage. They set "accidental" fires to outbuildings or damaged tools. Some became so desperate that they murdered their own children rather than let them become the property of the master.
For a slave, this was the ultimate act of sabotage.
One common method of defying their master was to abscond. A slave would run away and hide–usually in the nearby woods–for a few days. A hunting party would be sent out and, if the slave could hold out long enough, the master would believe them to have run away. A runaway slave was big money lost but, the chances of actually reaching freedom were slim. An absconding slave didn’t intend to run away forever but scare their master just enough that they gave into some small demand (like better food or keeping the family together). In this way, a slave could take control of a bad situation.
Slaves making their way to freedom often left in the night. In pitch darkness, they had only a few hours to get as far away as possible. Once they were found missing, bounty hunters would be hired to bring them back where punishment was certain.
On the Run
Slavery was big business–one field slave costs ten to fifteen times as much as the average farmer could make in a year– and slave owners were not going to simply let their property walk off to freedom. An entire economy developed around keeping slaves on the plantation. Each state set the distance is considered a slave to be a runaway. In Mississippi, a slave was a runaway if they were caught more than eight miles from their plantation without the proper papers. Each state hired patrols armed with rifles and bloodhounds to patrol the main road and waterways that a slave might escape from. The ten percent reward for returning an escaped slave was good money and many poor whites from the north and south took up the calling of the Patroller.
A slave attempting to escape north to freedom had the cards stacked against him. Most of the slaves who escaped were young men. Even before he stepped foot off the plantation he had to worry about his plan being given away by a slave looking to gain some favor with the master. Once he decided to leave, he often took off at night. The night was the safest way to travel to avoid the patrollers.
There was no map pointing the way to freedom – most slaves probably couldn’t have read it anyway. Therefore, slaves used geography to make their way north. Slaves looked for common landmarks, they felt the trees for the thickest patch of moss –because that’s the side that pointed north. The most reliable landmark was in the sky. In the northern hemisphere, the handle of the Little Dipper always points to the North Star, no matter what season.
Slaves escaped whenever and wherever they found a good opportunity. A slave escaping from Kentucky would logically make her way north to the Ohio River. This is the most heavily patrolled area but also the place where the abolitionists operating the Underground Railroad would be most active.
A Mississippi slave would try to escape west to Indian Territory. Many Native Americans welcomed escape slaves into their tribes where African-Americans and Native Americans married and had children.
A slave from Texas would logically head to Mexico where slavery was illegal. Patrollers would be hired to guard the Rio Grande River - which marked the border with Mexico. Texas had its own natural patroller. The harsh desert climate, venomous snakes, and scorpions killed more than a handful of escaped slaves.
Henry "Box" Brown: The Man Who Mailed Himself to Freedom
Henry "Box" Brown pulled off one of the wildest escapes from slavery you’ll ever hear about. Born in Virginia, he had already endured more than anyone should, including the heartbreaking sale of his wife and kids to another plantation. Determined to break free, Henry came up with a plan so crazy it just might work—he decided to mail himself to freedom.
With help from some friends, Henry climbed into a wooden crate barely big enough to hold him. The box was labeled “Dry Goods” and shipped to Philadelphia. Inside, he packed a little water, a few biscuits, and a whole lot of hope. The journey took 27 hours, and it was anything but smooth. He was tossed around, dropped, and even left upside down for so long that the blood rushed to his head, making his eyes feel like they were going to pop out. But Henry didn’t make a sound—he knew that being caught could mean death.
When the box finally arrived, Henry’s friends carefully opened it, and out he climbed, bruised and battered but free. His first words? “How do you do, gentlemen?” Cool as a cucumber, even after such an insane journey.
Henry didn’t stop there. He turned his story into a rallying cry against slavery, traveling and speaking out about his escape and the horrors of bondage. His boldness and creativity made him a hero, showing just how far someone would go to claim their freedom.
Runaways in Disguise
Our favorite freedom story is of Ellen and William Craft, a married couple who lived on nearby plantations in Macon, Georgia. Ellen was a light-skinned house slave, the daughter of a slave and a white planter. In 1848, Ellen disguised herself as a white male planter traveling with his black “manservant”. To disguise the fact that neither could read nor write, Ellen wore a sling on her writing arm.
Ellen had a trusting master who allowed her to take trips into town. For months the co-conspirators found a way to obtain the papers and tickets necessary to make their escape. On December 21, they boarded a train to Savannah and from there a steamship to Philadelphia.
It was William’s idea to hide in plain sight. Unlike most slaves who hid in swamps or in the blazing hot holds of a ship, the Crafts made their way to freedom in style. First class tickets and hotels the whole way. With their disguises in place, they traveled with the rich and powerful. The whole time they traveled in constant fear of being discovered. At one point Ellen was forced to sit next to the neighbor of her master; an influential judge who dined often at her master’s home.
Once they arrived in Philadelphia they became celebrities of the abolitionist circles. Like Frederick Douglass, they did speaking tours talking about the evils of slavery. Like Douglass, they also lived with a huge bounty on their heads and finally escaped to England where they raised their five children in freedom.
William and Ellen Craft
Fugitive Slave Act
One of the biggest complaints that southern plantation owners had was that the Fugitive Slave Act of 1793 wasn't working because northern states refused to enforce it. The law was supposed to require runaway slaves to be returned to their masters. The police often looked the other way and sometimes anti-slavery mobs prevented slave catchers from doing their jobs.
Slave catching was big business and the loss of runaway slaves was costing the South millions of dollars. Almost 1,000 slaves ran away each year- many on the Underground Railroad that spirited slaves to freedom using a series of safe houses and clever disguises. Southerners demanded a tougher fugitive slave act and they got it. The Fugitive Slave Act of 1850 made it a crime for anyone, even police, to help a runaway slave.
John Calhoun, that staunch pro-slavery Senator from South Carolina, even proposed that the United States have two presidents- one from the North and one from the South. This idea was turned down.
The real victory of the Compromise of 1850 was that the Missouri Compromise was declared dead. New territories would now be allowed to choose for themselves whether slavery would be allowed and whether they would eventually join the Union as a free or slave state.
Some wagons used to carry escaping slaves had hidden compartments built in
Attics, hidden rooms, and cellars were used to hide runaway slaves if the police showed up asking questions
Harriet Tubman: Heroine of the UR
You simply can’t have a discussion about the Underground Railroad without talking about Harriet Tubman, or “Moses” as she was often called. She was one of the escaped slaves from Maryland in the 1840's and she became one of the major “conductors” in the underground network. She was so courageous that she even returned to Maryland two years after escaping so she could help the rest of her family get to freedom. But that wasn't the only return trip she had. She made more than a dozen trips back to the South via the Underground Railroad to help free slaves. In all, she is reported to have helped at least 150 slaves escape from their brutal slaveholders despite the fact that she would have surely been killed if she ever showed her face in the South after her initial escape.
The Underground Railroad:
Many people picture the Underground Railroad as a path or road northward to freedom. In reality, it's better to think of the Underground Railroad as a scattered collection of safe houses that spread across the country. These safe houses could be a cabin in the woods, a church, or a barn. Each location was a beacon of hope for those escaping the horrors of slavery, offering a temporary haven where they could rest, eat, and regroup before continuing their dangerous journey.
The people who ran these safe houses, known as "conductors," risked everything to help freedom seekers. Some were free Black individuals who knew firsthand the importance of liberty; others were abolitionist allies of various backgrounds who believed deeply in the cause of freedom. They communicated through whispers, secret signs, and coded messages, using quilts, lanterns, or even specific songs to indicate whether it was safe to approach.
Far from being a single, linear route, the Underground Railroad was a network as diverse as the people who used it. Routes twisted and turned, adapting to the dangers of the moment. The journey could take weeks, months, or even years, with enslaved individuals traveling by foot, wagon, or boat under the cover of darkness.
The final destination for many was Canada, where slavery had been abolished, but freedom seekers often found relative safety in northern states. Along the way, they relied on their own resilience and the courage of strangers who believed in a shared humanity. The Underground Railroad wasn't just a road to freedom; it was a testament to the power of solidarity and resistance in the face of oppression.
The final stop on the Underground Railroad wasn't always Canada. Mexico outlawed slavery in 1810; and many slaves headed south of the border or integrated with Indian tribes.
"... Buffalo (New York) being a place through which many fugitives passed while on their way to Canada. Mr. Brown spent much time in assisting those who sought his aid. His house might literally have been called the 'fugitive's house.' As Niagara Falls were only twenty miles from Buffalo, slaveholders not unfrequently passed through the latter place attended by one or more slave servants. Mr. Brown was always on the look-out for such, to inform them that they were free by the laws of New York, and to give them necessary aid. The case of every colored servant who was seen accompanying a white person was strictly inquired into, Mr. Brown's residence also became the home of Anti-Slavery agents, and lecturers on all reformatory movements."
Daughter of William Wells Brown, abolitionist and conductor.
Why It Matters
The stories of enslaved people who risked everything to escape, whether through the Underground Railroad or other daring acts, are a powerful reminder of the human spirit’s resilience. They highlight how individuals can challenge even the most entrenched systems of oppression, inspiring movements for justice and equality that continue to this day. These acts of defiance also reveal the lengths to which people will go to reclaim their freedom, showing us that the fight for liberty and dignity is universal and timeless.
Understanding these stories not only honors the courage of those who fought against slavery but also helps us recognize the roots of systemic injustice. By learning about this history, we can better appreciate the struggles of marginalized communities and the ongoing need to stand up against inequality in all its forms. These narratives aren’t just history—they’re a call to action, urging us to work toward a fairer and more just world.
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