By Dark Files HQ Editorial Team · Published 4 April 2026 · Updated 22 October 2026

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Nine of the most daring prison escapes in history

Nine remarkable real prison escapes, from Alcatraz in 1962 and the Great Escape from Stalag Luft III to Colditz, the Maze Prison break and El Chapo's tunnel: how they were done and what happened next.

Prison escapes fascinate us because they combine ingenuity, patience and huge risk. These nine are among the most famous. Some were heroic wartime breakouts; others were by dangerous criminals whose escapes put the public at risk.

1. Alcatraz (1962)

In June 1962, Frank Morris and brothers John and Clarence Anglin escaped from Alcatraz, the high-security prison in San Francisco Bay. Over months, they dug through the walls of their cells using sharpened spoons and improvised tools, left papier-mâché dummy heads in their beds, and paddled away on a raft made from more than 50 stolen raincoats. They were never found. The FBI closed its investigation in 1979, concluding they probably drowned, but the US Marshals Service still keeps the case open.

2. The Great Escape (1944)

In March 1944, 76 Allied airmen escaped from the German prisoner-of-war camp Stalag Luft III through a tunnel nicknamed "Harry". Only three reached safety. Of the 73 recaptured, 50 were executed on Hitler's orders, a war crime later prosecuted. The escape inspired the 1963 film, which took liberties with the facts.

3. Colditz

Colditz Castle in Germany held Allied officers considered escape risks during the Second World War. Despite its reputation, there were dozens of successful escapes. Airey Neave became the first British officer to make a "home run" from Colditz in 1942, escaping disguised in a homemade German uniform. Prisoners even built a glider in the attic, which was never flown before liberation.

4. Libby Prison (1864)

During the American Civil War, 109 Union officers escaped from Libby Prison in Richmond, Virginia, through a tunnel dug from the cellar. Around half reached Union lines.

5. John Dillinger and the "wooden gun" (1934)

The American gangster John Dillinger escaped from a jail in Crown Point, Indiana, reportedly using a fake gun carved from wood and blackened with shoe polish. The episode embarrassed the authorities. He was shot dead by FBI agents later that year.

The American gangster John Dillinger escaped from a jail in Crown Point, Indiana, reportedly using a fake gun carved from wood and blackened with shoe polish.

6. Ronnie Biggs (1965)

Ronnie Biggs, one of the Great Train Robbers, escaped from Wandsworth Prison in London in 1965 by climbing a rope ladder over the wall into a waiting removal van. He spent decades abroad, mostly in Brazil, before returning voluntarily to the UK in 2001 and being sent back to prison.

7. The Maze Prison escape (1983)

In September 1983, 38 republican prisoners escaped from HMP Maze in Northern Ireland, the largest prison escape in UK history. A prison officer died of a heart attack after being stabbed during the escape, and others were injured. Many escapees were recaptured within days.

8. Helicopter escapes

Several prisoners, particularly in France, have escaped by helicopter, with accomplices hijacking or hiring aircraft to land in prison yards. The French criminal Pascal Payet was involved in more than one, both escaping himself and helping others.

9. El Chapo's tunnel (2015)

In July 2015, the Mexican drug lord Joaquín "El Chapo" Guzmán escaped from a maximum-security prison through a hole in his shower area leading to a tunnel of more than a mile, fitted with lighting, ventilation and a motorbike on rails. He was recaptured in 2016, extradited to the US, and sentenced to life imprisonment in 2019.

What escapes changed?

Many escapes led to major security reviews. After the Maze breakout, an official inquiry criticised security failures. Modern prisons use layered perimeters, CCTV and anti-helicopter netting, partly because of escapes like these.

Sources and further reading

• FBI: A Byte Out of History, Alcatraz escape
• Wikipedia: Stalag Luft III
• Wikipedia: 1983 Maze Prison escape
• Wikipedia: Colditz Castle

Facts checked on 20 October 2026. Spotted an error? Tell us and we will correct it.

Chris Adeyemi Research Editor

Chris is a freelance writer and editor covering a wide range of topics with a focus on accuracy and depth.

Last updated: 2026-04-25 · Fact-checked by editorial team