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The Greatest Escapes in Military History

History · 9 escapes · ~9 min read · Updated October 2026

Napoleon's brig Inconstant meets the French brig Zéphir on the way back from Elba, 28 February 1815, painted by Ambroise Louis Garneray
At a glance
EscapeDateWhoOutcome
1Charles II after Worcester1651The defeated kingReached France
2Napoleon from Elba1815The exiled emperorBack in Paris in 19 days
3Churchill from Pretoria1899A war correspondentReached neutral territory
4Neave from Colditz1942A British lieutenantFirst British home run
5Piechowski from Auschwitz1942Four prisonersDrove out in SS uniforms
6Pilecki from Auschwitz1943The camp's underground leaderEscaped to write his report
7The Wooden Horse1943Three airmenAll three reached Britain
8The Sobibor uprising1943About 600 prisonersAbout 300 out, some 50 survived
9The Great Escape194476 airmen3 home, 50 murdered
Quick answer

The greatest escapes in military history include Napoleon's flight from Elba in 1815, Winston Churchill's escape from a Boer prison in Pretoria in 1899, Airey Neave's escape from Colditz in 1942, the Sobibor uprising of 1943, in which some 300 prisoners broke out of a death camp, and the Great Escape from Stalag Luft III in 1944, when 76 airmen got out and only three reached home.

Escape is one of the oldest dramas of war, and one of the few in which a single person, with a forged pass, a home-made uniform or a stolen car, can beat an entire system. The stories below are all documented, in the escapers' own reports, in the files of those who hunted them, and by historians.

They are not all the same kind of story. A defeated king hiding in a tree and an emperor sailing home to reclaim a throne belong to one world; prisoners breaking out of Auschwitz and Sobibor belong to another, where escape meant survival itself and every success could cost others their lives. We tell them in order of date.

With a forged pass, a home-made uniform or a stolen car, one person could beat an entire system.

1. Charles II and the Royal Oak (1651)

On 3 September 1651 the army of the young Charles II was destroyed by Parliament's forces at Worcester. Charles rode north with several hundred followers, then left them to travel in disguise as a countryman, guided by the five Penderel brothers, Catholic tenants who knew every hiding place in the Shropshire woods. At dawn on 6 September he reached Boscobel House, and that day he and Major William Careless hid in a pollarded oak1 while soldiers searched the wood below. Later, disguised as the servant of a Royalist gentlewoman, Jane Lane1, he worked his way to Shoreham in Sussex and sailed for France, about six weeks after the battle. When he was restored in 1660, 29 May became Oak Apple Day.

Painting of two men hiding among the branches of an oak while soldiers search the woods below
Charles II and William Carlos, the Major Careless of the story, hiding in the Royal Oak, one of a series of five paintings of the escape by Isaac Fuller (died 1672), made after the Restoration. Public domain

2. Napoleon leaves Elba (1815)

Sent to Elba in 1814 as ruler of a small island, Napoleon watched France tire of the restored Bourbons. On 26 February 1815 he slipped away by sea, and on 1 March landed at Golfe-Juan near Cannes with about 1,100 soldiers2. Avoiding royalist Provence, he marched north through the foothills of the Alps along the road now called the Route Napoléon. On 7 March, at Laffrey, he met the 5th Line Regiment sent from Grenoble to stop him. According to the Fondation Napoléon's account, he walked forward and called out: "If there is one amongst you who wishes to kill your Emperor2, here I am." The soldiers joined him. On 20 March he entered the Tuileries, just abandoned by Louis XVIII. The Hundred Days that followed ended at Waterloo.

3. Churchill escapes from Pretoria (1899)

In November 1899 Winston Churchill, aged 24 and reporting the Boer War for the Morning Post, was captured when Boer commandos ambushed an armoured train in Natal. Held with British officers at the State Model School in Pretoria3, he climbed the wall on the night of 12 December and walked out through the town. He jumped a goods train and, lost and exhausted, knocked at a house near a coal mine. By sheer luck it belonged to John Howard, an English mine manager3, who hid him down the mine and then smuggled him onto a train among bales of wool. Churchill reached Lourenço Marques in neutral Portuguese East Africa, a hero at home.

A line of British soldiers in helmets and caps under guard, with Churchill standing apart at the right
British prisoners taken with the armoured train in November 1899; Winston Churchill stands apart on the right. The photograph was taken after they were brought to Pretoria. Public domain

4. Airey Neave walks out of Colditz (1942)

Colditz Castle in Saxony was where the Germans sent officers they considered persistent escapers. Airey Neave, a British lieutenant wounded and captured at Calais in 1940, arrived there in May 1941 after an earlier escape had failed. On the night of 5 January 1942 he and a Dutch officer, Lieutenant Anthony Luteyn, dressed in German uniforms made in the camp and carrying forged papers, got out through the floor of the camp theatre and walked past the guards. They reached Switzerland, and Neave became the first British officer to escape from Colditz4. He went on to work for MI9, the British intelligence department that helped Allied servicemen evade capture.

5. Kazimierz Piechowski drives out of Auschwitz (1942)

On Saturday 20 June 1942 four prisoners pushed a cart out through the gate marked Arbeit macht frei: Kazimierz Piechowski, Stanisław Jaster, Józef Lempart and Eugeniusz Bendera, a mechanic who had learned he was listed for death. They had invented a four-man work detail so that no one from a real work party would be punished, because the camp killed ten prisoners for every escaper5. In a storeroom they put on SS uniforms; Bendera brought round the best car in the SS garage, a Steyr 220 usually said to be the commandant's own, and Piechowski, who spoke German, sat as the officer. At the final barrier he leaned out and waved, and the guard lifted it. All four got away. The Germans killed Lempart's mother and Jaster's parents in reprisal5. Jaster carried out a report from Witold Pilecki's underground, but did not survive the war: wrongly suspected of treachery, he was shot by the underground in 1943.

The iron gate of Auschwitz I with the Arbeit macht frei sign above it
The main gate of Auschwitz I with the words Arbeit macht frei, photographed in 2012. Piechowski and his companions pushed their cart out through this gate on 20 June 1942. Jorge Láscar, CC BY 2.0

6. Witold Pilecki leaves the camp he chose to enter (1943)

Pilecki had let himself be arrested in Warsaw in 1940 so that he could be sent to Auschwitz and build a resistance network inside it. By the spring of 1943, fearing that he would be exposed, he decided to go. With two fellow prisoners, Jan Redzej and Edward Ciesielski, he arranged to be put on the night shift in a bakery outside the main camp. On the night of 26 to 27 April 1943 Redzej loosened the bolts of the bakery's iron door with a spanner obtained in secret; while one of the two SS guards was writing a letter and the other was eating, the three pushed the door open and ran into the darkness. Pilecki then wrote one of the most detailed reports on the camp to reach the Polish underground.

7. The Wooden Horse, Stalag Luft III (1943)

Stalag Luft III, the air force prison camp at Sagan, today Żagań in Poland, was built on sandy soil precisely to make tunnelling impossible. Three prisoners found a way round it. Day after day a hollow vaulting horse made from Red Cross boxes was carried out to the exercise yard with a digger hidden inside, and while other men vaulted over it, a short tunnel was dug from beneath it towards the wire. On 29 October 1943, after 114 days of digging6, Michael Codner, Oliver Philpot and Eric Williams broke out. All three reached Britain.

8. The Sobibor uprising (1943)

Sobibor, in eastern Poland, was not a prison camp but a killing centre: the SS and their auxiliaries murdered at least 167,000 people there7, almost all of them Jews. By the autumn of 1943 the prisoners kept alive for labour knew that the camp was winding down and that they would be killed. Led by Leon Feldhendler and Alexander Pechersky, a Soviet Jewish officer, they planned a revolt. On 14 October 1943, with about 600 prisoners left in the camp, they killed 11 German staff and a few guards7, and around 300 broke out under fire. About 100 were caught in the manhunt that followed. Some 50 survived the war. After the revolt the Germans shot the prisoners who had not escaped and dismantled the camp.

9. The Great Escape, Stalag Luft III (1944)

The camp's most famous break-out was a year in the making. Under Squadron Leader Roger Bushell, hundreds of men forged papers, tailored civilian clothes and dug three tunnels code-named Tom, Dick and Harry. On the moonless night of 24 to 25 March 1944, 76 men crawled through the 102 metres of Harry6 before the 77th was spotted; the tunnel had come up short of the woods. All but three were recaptured. On Hitler's orders, 50 of them, Bushell among them, were murdered by the Gestapo. The three who made it home were two Norwegians, Per Bergsland and Jens Müller8, and a Dutchman, Bram van der Stok.

Memorial stones in a pine wood with an inscription to the Great Escape and a stone strip running towards them
The memorial at Żagań to the Allied airmen of the Great Escape, unveiled in 2004; the stone strip in front marks the line of the tunnel Harry. Photographed in 2015. CC0

Why these escapes still matter

Films have turned several of these stories into adventures, but the escapers knew the price. The men of the Great Escape were executed for leaving a camp. Piechowski and his friends had to invent a fake work party so that innocent men would not be shot in their place, and still their families paid. At Sobibor, escape was not a sport but the only answer to murder. What these stories share is a refusal to accept that the wire, the walls or the guards had the last word.

To read more about the man who walked into Auschwitz of his own free will, see our page on Witold Pilecki, or turn to the Warsaw Uprising, where he fought the following year.

Frequently asked questions

What is the greatest escape in history?

The Great Escape of 1944 is the most famous; the Sobibor uprising of 1943 was one of the largest break-outs from a Nazi death camp; Napoleon's escape from Elba in 1815 had the biggest consequences, leading to the Hundred Days and Waterloo.

How many men escaped in the Great Escape?

Seventy-six men got out through tunnel Harry on 24 to 25 March 1944. Seventy-three were recaptured, 50 of them were murdered by the Gestapo, and three reached safety.

Did anyone escape from Auschwitz?

Yes. By the most widely cited count, at least 802 prisoners tried and 144 succeeded, among them Kazimierz Piechowski and three companions, who drove out in a stolen SS car in June 1942, and Witold Pilecki, who escaped in April 1943.

Did anyone escape from Colditz?

Yes. Airey Neave was the first British officer to do so, reaching Switzerland in January 1942.

How did Napoleon escape from Elba?

He simply sailed away. On 26 February 1815 he left the island with his small guard, landed at Golfe-Juan on 1 March with about 1,100 soldiers, and reached Paris on 20 March as the royal army went over to him.

How did Churchill escape from the Boers?

He climbed the wall of the prison in Pretoria on 12 December 1899, jumped a goods train, was hidden in a coal mine by an English manager, and was smuggled out by rail to Portuguese East Africa.

Sources and notes

Numbered notes in the text point to the works below.

  1. English Heritage, “History of Boscobel House and the Royal Oak” ↩ a b
  2. Fondation Napoléon, “The Route Napoléon” ↩ a b
  3. Candice Millard, Hero of the Empire: The Boer War, a Daring Escape and the Making of Winston Churchill (Doubleday, 2016). ↩ a b
  4. The National Archives (UK), “Escaping Colditz” ↩
  5. dzieje.pl (Muzeum Historii Polski / PAP), “Rocznica brawurowej ucieczki więźniów Auschwitz” ↩ a b
  6. The National Archives (UK), “Great Escapes (exhibition)” ↩ a b
  7. United States Holocaust Memorial Museum, “Sobibor” ↩ a b
  8. Guy Walters, The Real Great Escape (Bantam Press, 2013). ↩

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