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Great Escapes dressed as a woman

Throughout history there have been incidences when a man has used the clothing and appearance of a woman, as a disguise in order to aid an escape from a prison and/or to fool unsuspecting pursuers. Some of these people were prominent figures in their time and others simply made a name for themselves from their escape activities. The following (escape from the Tower of London, Jacobite Ecsape, The Infamous Escaper, Colditz escapes, London Escape) are some of those stories and although each one is very different from the others, one fact does stand out. They are all very innovative and daring for their time.

Escape from the Tower of London:

Following the first Jacobite Rebellion in January 1716, The Earl of Derwentwater, Viscount Kenmure and lord Nithsdale were imprisoned in the Tower of London on the charge of high treason awaiting their executions.


On the evening of 23 rd February Lord Nithsdale was visited by his wife in his final hours. She brought with her a servant and some ale for the guards. She was intending to try to help her husband escape and came with that purpose in mind. She sat for a while and talked to her husband while outside the guards were enjoying their ale. She needed to give the guards a period of time free from any disturbances so that the ale had time to take effect. After an hour or so she left the prison and went outside to fetch her servant and they both went back into the prison cell.

The Servant was wearing two sets of clothes and as the guards were somewhat occupied with their ale took little or no notice of the servant. Lady Nithsdale set about putting white powder paint on her husband's face in order to hide several days beard growth and some red powder paint for the cheek areas. She dressed him up in the spare set of clothes that the servant had been wearing and a cloak to help hide his face. Lady Nithsdale's servant and Lord Nithsdale disguised as a servant made their escape passed the guards, who were by this time preoccupied with their ale.

Lady Nithsdale stayed in the prison cell alone and pretended to talk to her husband. This was a brave and yet clever trick as it gave her husband and the servant time to escape. On leaving the cell herself some hours later, she instructed the guards that her husband was praying and that he shouldn't be disturbed until morning. Their escape went undetected and the couple fled to Italy where they spent the rest of their lives. On the morning of the 24th of February 1716 the Earl of Derwentwater and Viscount Kenmure were beheaded on Tower-hill for the crime of high treason.

Jacobite Escape:

It was some years later in 1746 after the final Jacobite Rebellion when another prominent Jacobite figure, namely Charles Edward Stuart (Bonnie Prince Charlie) used the disguise of a woman to flee the English Army that was chasing him. Following the battle of Culloden on 16 th April 1746, Charles was on the run whilst trying to escape from the English forces who had been hunting for him since the battle.

A huge reward of £30,000 for his capture was offered but over the next five months Charles was kept out of the English hands by loyal supporters who continued to help him and support his cause.

By the end of April he had sailed to the Outer Hebrides, remaining there for the next two months. Flora McDonald helped him by disguising Charles as a serving maid in order to evade capture. They reached Portree on the Isle of Skye a few days later and the Prince parted company with Flora on 1 st July.

Eventually, on 20 th September, he embarked from Arisaig for France in a French ship which had been sent to collect him. He died in Rome on 31 January 1788 and was buried at a church in Frascatti.

The Infamous Escaper:

Jack Sheppard was born in London in 1702 to a working class family. Like so many others his future was that of poverty and uncertainty unless he was taken on as an apprentice to learn a trade. Apprentices were effectively enslaved to their masters for many years. They received only their keep, and were locked up at night and compelled to live by strict rules.

Apprentice boys had a reputation for being hooligans because they so often resorted to a life of theft and other crimes. A life that was too often cut short by the gallows! Jack had developed a taste for the good life after living on the spoils of crime, and it was these crimes that led him to his life of notoriety. He was eventually caught and put in jail for theft, where he promptly escaped, only to be caught again for stealing some days later.

He escaped and was soon caught before being jailed again. After appearing in court for the crimes of stealing two silver spoons, a roll of cloth, and £7 in cash amongst others, he was found guilty and sentenced to the gallows. By now Jack's exploits had made the newspapers and his fame as a notorious thief had spread across London.

Jack was determined to escape and with the help of two prostitutes made his most daring escape to date dressed as a woman!

On 31st August 1724, Polly and Bess two prostitutes whom he had known from one of the taverns that Jack had frequented visited him at Newgate prison. Bess smuggled in a saw, a long dress and a cloak about her person and gave them to Jack through the bars on his cell. Bess and Polly then needed to divert the guard's attention from what Jack was doing, so they pretended to hold a somewhat noisy and flirtatious conversation with Jack.


Meanwhile, Jack sawed through one of the spikes on the top of his cell door so as to make a bigger hole from which to squeeze through. Jack changed into the ladies clothes that had been brought in, and placed the cloak over the top so that the hood covered his head and climbed over the door. Then, when the guards were sufficiently distracted made his escape from the prison disguised as Polly, walked passed the guards and to freedom once again. The real Polly was by now elsewhere hiding in the prison and made her exit sometime later. The story doesn't end there, as Jack was eventually captured and sent back to Newgate prison where he escaped for a fourth time. All of Jack's exploits had made him a household name through extensive newspaper coverage, which was to add to his fame as one of the leading criminals of the day.

Jack was finally hanged on 16 th November 1724 at Tyburn, infront of a reputed 200,000 people, who came to watch the event, not to gloat but in the hope that their hero would escape at the last minute, which was not the case.


Colditz Escapes: 

On 5 th June 1940, Captain Pat Reid was sent to Oflag VII. C prison camp at Laufen about fifteen miles northeast of Salzburg. It was here at 05.30hrs on September 5 th that year that he made his first escape from a prisoner of war camp. His plan was to escape through a tunnel with three friends all in female disguises and to get as far away from the town as he could. He thought that if the Germans had discovered his escape too early, they would be looking for a man and not a woman. Their female clothing consisted of a coloured handkerchief as a headscarf, a white sports shirt, which would double up as a blouse and a skirt made from a pair of curtains. They shaved their legs and used iodine to give them a sunburnt look and wore black plimsolls on their feet.

They had a few problems getting clear of the camp and were clear of the town shortly after dawn. Once safely in the woods and out of site they changed back into male attire and continued on their way. They made good progress and by the fifth day had reached the town of Lungotz about seventy five miles away from the camp on the way to the Yougoslavian boarder. They entered the town just before midnight and as they were walking through the town a light shone on them from one of the houses. They continued and headed out of the village as quickly as they could and into the woods. As they rested they heard a rustling from the undergrowth behind them and a voice saying “halt." They had been caught and their bid for freedom had failed. They were taken back to the camp in Laufen before on 7 th November that year being transferred to a new camp Oflag IV. C, which was better known as Colditz Castle.

The infamous Colditz Castle was home to a number of allied prisoners who longed for freedom by trying to escape. Prisoners at the castle were often taken down to the nearby park under guard for exercise. On 5th June 1941 a Frenchman Lieut. Chasseur Alpin Bouley (see photo) decided to make a novel and daring escape. He had me his way out of a window into the outer courtyard and down the wall onto the main pathway leading to the castle.

It was at this time that some prisoners were returning from the park and nearing the castle paused by a gate leading out to let a German woman through who was dressed in a skirt suit and hat. The German guards said nothing, but as the woman walked away from the castle, one of the prisoners noticed she had dropped her watch. "Hey, Fräulein, your watch!" he said. She didn't respond, so a guard went after her and found "her" to be “him”! This unknowing act cost Lieut. Bouley his chance of freedom and was taken back to the castle with the others. The story doesn't quite end there, because on 15 th October 1942 Captain Reid did escape from Colditz but dressed this time as a German Officer and made his way back to England.


The London Escape:

On the 12 th February 1682, Count Konigsmark, a Swedish diplomat living in London, murdered Thomas Thynne Marquis of Bath and Member of Parliament, as he was being driven down Pall Mall in London. The authorities received a tip off that a man disguised as a woman had attempted to leave the country from the docks at Gravesend. Konigsmark is caught and charged with murder along with his accomplices. They were convicted and hanged in Pall Mall, at the scene of their crime some days later, but Konigsmark who had bribed the judge and jury was curiously acquitted and permitted to leave the country. He was to die a few years later, as a soldier of fortune, while taking part in the siege of Argos against the Turks.