Tudor prison escapes weren’t just the stuff of legend—they were real, daring, and often shockingly inventive. While the Tower of London tends to dominate popular imagination, the truth is that escape attempts happened across a wide range of Tudor-era prisons, from drafty manor houses to crumbling castles and even coastal inns.
Let’s dive deep into the wildest and most creative Tudor prison escapes that didn’t happen at the Tower. You’ll meet reformers who faked their deaths, noblemen who rappelled down castle walls, and priests who slipped away disguised as servants. These true stories reveal the cracks in Tudor England’s justice system—and the courage, cunning, and audacity of those who dared to break free.
Transcript of Great Escapes: Wild Tudor Prison Breaks (That Weren’t at the Tower)
This week, we’re going to talk about great escapes—Tudor prison breaks. A couple of years ago—gosh, maybe five years ago, must have been five or six—I did an episode on the top escapes from the Tower of London. It was based on a talk I gave at the Intelligence Speech Conference about the most daring escapes from the Tower.
I’ve also been talking about prisons recently. We did that episode on Tudor justice and the law, so I thought it would be fun to go back and revisit some of that—expand it, actually—so we’re not just talking about prison breaks from the Tower of London anymore, but the most daring prison escapes of Tudor England as a whole.
Of course, when most of us think about prison in Tudor England, we think of the Tower of London. It’s the most iconic and famous prison—but there were others. So today, we’re going to break out of the Tower—literally—because while the Tower of London saw its fair share of escape attempts (some successful, some… let’s just say, headless), there were other Tudor prisons as well.
Some were formal castles used to detain high-status prisoners. Some were city jails or even private homes repurposed as detention centers. Others were improvised—on ships, in monasteries, in the back rooms of inns. And it turns out that outside the shadow of the Tower, the escapes could be just as wild.
From clever disguises and bribed jailers to secret codes and fake suicides, Tudor prisoners came up with some very creative schemes to win their freedom. So today, I’ve pulled together some of the best non-Tower Tudor jailbreaks.
We’ll hear about the Protestant reformer who faked his own death to escape across the sea. We’ll scale the castle walls with an Irish lord who wasn’t done causing trouble. And we’ll hide among Catholic priests sneaking out through secret passageways. Okay, I’m going to cheat just a little and include one final Tower escape—because it’s just too good not to.
Let’s kick it off with one of my favorites: a dramatic escape involving a set of clothes, a staged drowning, and a swift exit to Germany. Robert Barnes was not your average prisoner. He was once a respected prior of the Augustinian Monastery in Cambridge.
A scholar with a sharp tongue and an inconvenient enthusiasm for Martin Luther.
He had traveled to Germany and met the man himself. He believed in reform. He believed the scriptures should be available to the people—and most dangerously of all, he believed that Henry VIII might one day be persuaded to believe it too.
By the late 1520s, Barnes had already gotten himself into trouble. He preached a fiery sermon on Christmas Eve in 1525, calling out church corruption and quoting Luther right there in the pulpit. That landed him in a heresy trial and a spell in prison, but he wriggled out of that one—likely with some influential help behind the scenes.
Fast forward to 1528. He’s back in England, and once again, he finds himself under suspicion. The exact details are a little murky. He may have returned quietly, or perhaps he was arrested while trying to get back in. What we do know is that he was in danger. Heretics didn’t get many second chances under Henry, and the reformers were increasingly being used as pawns in the political games of Thomas Wolsey and Thomas More.
So, Barnes decided to disappear. According to multiple accounts, he staged his own death. He left a pile of clothes near a riverbank, making it look as though he had thrown himself into the water and drowned. No body was found, of course—but that only added to the plausibility. Maybe he’d been swept downstream. Maybe the fish got to him. Maybe the judgment of God had intervened.
But in reality, he was alive—and already halfway to Germany. He managed to reach Wittenberg, where he reconnected with his old Protestant contacts and lived under the protection of German reformers. He worked closely with Martin Luther, translating texts, writing tracts, and staying one step ahead of Henry’s agents.
Barnes’s suicide was so convincing that for a while, the authorities truly believed he was dead. It wasn’t until much later—when his name popped up again in reformist circles—that they realized they’d been duped. By then, Barnes had become a kind of Protestant celebrity: the Englishman who outfoxed the Tudor state with nothing more than a discarded cloak and a river.
He eventually returned to England under Cromwell’s protection, a sign of how much the tide had temporarily turned. He even acted as a sort of go-between in diplomatic missions with the Germans. But, as we all know, Cromwell’s downfall in 1540 brought his friends down with him.
Barnes was arrested again, tried as a heretic, and this time, there was no escape. He was actually burned at the stake on July 30th, 1540—the same day that Cromwell was executed. Still, that riverbank trick? Absolute legend.
All right, now let’s move on to Irish rope tricks: the Earl of Desmond escaping Dublin Castle. So we’re going to head over to Ireland. Dublin Castle wasn’t just a symbol of English authority in Ireland—it also doubled as a prison, especially for those noblemen the Crown found inconvenient but not yet execution-worthy.
And one of the slipperiest of these noblemen was Gerald FitzGerald, 14th Earl of Desmond. The FitzGeralds of Desmond were a powerful Anglo-Irish dynasty with a long history of rebellion. Gerald was no exception.
In the early 1570s, as tensions mounted between the Irish chieftains and the English government, Desmond found himself caught up in the usual web of politics, suspicion, and outright hostility. He was summoned to Dublin under the guise of negotiations, but of course, once there, he was promptly imprisoned.
Now, Desmond wasn’t actually kept in a high-security unit. His imprisonment at Dublin Castle was typical for a high-ranking noble—locked away, certainly, but definitely not chained to the wall. And he had help, either from sympathetic jailers or from his own men, who had managed to smuggle in some supplies.
Whatever the case, Desmond pulled off one of the great noble escapes of the period. One night in 1573, he fashioned a makeshift rope—probably from bedsheets or other linen materials tied together—and used it to lower himself down from a window in the castle.
There are conflicting reports about exactly how far the drop was, or how secure the knotwork turned out to be, but the point is: he made it out. And once he hit the ground, he had followers waiting nearby to whisk him away.
Desmond didn’t just escape and vanish quietly into the countryside. He went on to lead the Desmond Rebellions, a major series of uprisings against English rule in Munster. His escape was no fluke or act of desperation. It was a calculated first step in a broader campaign against the English presence in Ireland.
The English, of course, were absolutely furious. A nobleman slipping out of a castle prison using rope tricks was both an embarrassment and a pretty big security warning. Desmond was back in the wild, and his jailbreak became a symbol of Irish defiance—bedsheets and all.
Now we’re going to talk about the Great Wisbech getaway: the Catholic priests on the run. So we’re going to turn to a different kind of prison—one without bars or moats, but no less dangerous for the people trapped inside it. Welcome to Wisbech Castle, a Tudor bishop’s residence turned prison, located in the flat and windswept Fens of Cambridgeshire.
In the late Elizabethan period, it became something of a holding pen for high-profile Catholic recusants, priests, missionaries, and former monks who refused to conform to the Church of England. Unlike the Tower or Newgate, Wisbech wasn’t built for security. It wasn’t even really a castle by the time we’re talking about. It was more like a crumbling manor house with a perimeter wall and a lot of damp rooms.
But that didn’t mean the government wasn’t serious about keeping the men inside. Many of them were considered dangerous subversives, linked to foreign Catholic powers and accused of plotting treason as well as heresy.
Among those imprisoned were figures like Fr. William Weston, a Jesuit missionary who had returned to England in secret to minister to hidden Catholics. Life inside Wisbech was uncomfortable and tense. There were constant religious disagreements among the imprisoned clergy—rivalries between the Jesuits and the secular priests—and, of course, the always looming threat of execution if anyone fell afoul of Elizabeth’s increasingly paranoid administration.
Despite the conditions—and maybe because the place wasn’t exactly Alcatraz—there were several successful escapes. Some priests managed to bribe their jailers. Others used disguises, slipping out dressed as servants or tradesmen.
One particularly clever escapee is believed to have walked out wearing a borrowed cloak and hat, blending in with a group of workmen doing repairs on the roof. Catholic networks across England, especially in East Anglia and the Midlands, were skilled at moving fugitives from one safe house to another.
Once out of Wisbech, an escaped priest could usually rely on a string of sympathetic families—often wealthy women in remote country houses—who would hide them in secret priest holes or transport them in disguised carts.
Wisbech never saw a full-scale breakout, but the number of priests who quietly vanished from its walls was enough to worry the Privy Council. And while some were recaptured or eventually executed, many simply vanished into the vast patchwork of England’s underground Catholic resistance. For every priest who burned at Tyburn, there were others who managed to disappear with the help of a good cloak, a quick exit, and a network that believed their survival was a holy cause.
Next, we’re going to talk about John Gerard’s Tower escape. So, I know I said this episode was about escapes outside the Tower of London, but this one is just too good to leave out. It’s got invisible ink, daring rope work, nighttime rowing, and a priest with dislocated fingers. If you’re going to break your own rules, at least do it with style.
Let’s talk about Father John Gerard. Gerard was a Jesuit priest operating undercover in Elizabethan England—a time when that job description basically came with a death sentence. He was arrested in 1594 and thrown into the Tower, where he was interrogated, tortured, and kept under close watch.
But he never broke, even after being suspended by his wrists for so long that his shoulders dislocated. He refused to betray anyone in the Catholic underground. But Gerard wasn’t just resilient—this man was also resourceful. While still imprisoned, he managed to smuggle out letters written in invisible ink made from orange juice.
The trick was simple but brilliant. the juice wouldn’t show up on the page until it was held over a flame. These hidden messages helped coordinate his escape with allies on the outside. The plan was both daring and absurd. A rope would be thrown across the Tower moat from the outside, secured to a hidden anchor point inside his cell. Gerard would climb down the Tower wall, swing across the moat, and escape in a waiting boat. All this, while his hands were still healing from torture. His grip was weak, and the climb would’ve been brutal even for a healthy man. But Gerard was determined.
On the night of the escape in October 1597, the rope was secured as planned. Gerard slipped out of his cell, climbed down the Tower, and began to lower himself across the dark waters of the moat. One false move, and he either would’ve drowned or been caught and executed on the spot. But he made it.
His allies rowed him across the Thames, and by morning, he was gone. Unlike so many of these stories, this one actually has a happy ending—well, for a while, anyway. Gerard made it out of England entirely, escaping to the Continent, where he spent the rest of his life writing, teaching, and—fortunately for us—documenting everything.
He wrote The Autobiography of a Hunted Priest, which reads like a thriller. He describes the escape in vivid detail, including how the rope cut into his hands and how he and his friends laughed and cried once they were finally safe.
Gerard was one of the few prisoners to escape the Tower of London in the Elizabethan period, and he did it with stealth, smarts, citrus, and a truly terrifying amount of upper body strength. You can’t ask for a better jailbreak than that.
Now, we’re going to talk about some honorable mentions—stories that might not have earned full chapters in the history books, but still show how wide-ranging and sometimes downright ridiculous Tudor-era escapes could be.
First up: James Melville, the Scottish diplomat and court insider. In the early 1580s, Melville was placed under house arrest in England—more comfortable than a cell, but still meant to keep him quiet and under control. He managed to slip away, almost certainly with help from sympathetic contacts, and made it back to France, where he continued his diplomatic career. House arrest, it turns out, only works when your prisoner agrees to actually stay in the house.
Then there was the shadowy world of the Catholic smuggling networks, especially in the coastal towns. These weren’t one-off escapes, but entire systems designed to move fugitives out of England. Priests, former monks, even laypeople accused of recusancy could find safe passage—hidden in barrels, underneath loads of wool, or disguised as servants on merchant ships heading to Calais or the Low Countries.
You also had forged pardons. Yes, actual forged royal documents—sometimes slipped into the record or used to fool a gullible jailer. We don’t have many detailed examples that survive, but mentions of false protections appear in court records, suggesting that clever prisoners occasionally tried to paper their way out of captivity.
And finally, let’s not forget the escapes that hinged on sheer audacity. During the Marian persecutions, some Protestant reformers evaded arrest altogether by simply changing their names, relocating to a different parish, and laying low until Elizabeth came to the throne. It wasn’t glamorous, but it worked.
All in all, Tudor England was full of cracks in the system. Between corrupt officials, poorly guarded jails, and networks of allies, escaping wasn’t common—but it was absolutely possible if you had the nerve, the friends, or the rope… and maybe the orange juice.
So there you have it: riverbank suicides that weren’t, noblemen on bedsheets, orange-juice-coated letters, and priests vanishing in plain sight. For all the might of Tudor justice, the system had its blind spots—and every so often, someone found a way to slip through the cracks.
Related links:
Escape from the Tower of London: The Astonishing Tale of Alice Tankerville Wolfe
Tudor Justice: Crime, Punishment, and the Courts
Heather Teysko is the creator, writer, and producer of The Renaissance English History Podcast,  the original Tudor history podcast, started in 2009. She's been writing about history online for over 25 years, since her first site on Colonial American history became number one in history on Yahoo in 1998. In 2019 she created Tudorcon, which is now a yearly event, in addition to writing books, and running TudorFair.com - a whimsical Tudor Merch shop.
She has been passionate about Tudor England since she first read Alison Weir's The Six Wives of Henry VIII 30 years ago, and subsequently moved to London after college to spend her time immersed in Tudor history (how exciting when she got to interview Alison for the first time!). In addition to history, she is passionate about travel, and has lived in 3 countries and 4 states (not counting her perpetual state of confusion), and her family (who help her host her YouTube channel occasionally).
