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98 free Prison Escapes trivia questions with answers — history quiz, new questions added Aug 2026.
10 free prison escapes trivia questions with answers. Test your knowledge of history's most daring prison escapes with our engaging trivia quiz. From legendary breakouts to ingenious escape plans, this quiz covers some of the world's most famous prison breaks. Can you answer all 98 questions correctly?
30 of 98 questions with answers and explanations. Play the quiz
Q 01What stolen material did the 1962 Alcatraz escapees turn into a raft and life preservers?
Raincoats
The escapees stitched and glued stolen raincoats into a raft and life vests, following a life-preserver design one of them found in the March 1962 issue of Popular Mechanics.
Q 02Which drug lord twice escaped Mexican prisons, once in a laundry cart and once by tunnel?
Joaquín "El Chapo" Guzmán
Joaquín "El Chapo" Guzmán was wheeled out of Puente Grande in a laundry cart in 2001 and fled Altiplano in 2015 through a 1.5 km tunnel that opened under the shower in his cell.
Q 03The 1944 "Great Escape" saw Allied prisoners of war tunnel out of which German camp?
Stalag Luft III
Stalag Luft III, near Sagan in German Silesia, was the Luftwaffe-run camp from which Allied airmen broke out on the night of 24 March 1944 through a tunnel dug beneath the huts.
Q 04In The Shawshank Redemption, what hides the escape tunnel Andy Dufresne dug over 19 years?
A poster
A poster of Raquel Welch, after earlier pin-ups including Rita Hayworth, covers the hole Andy dug with his rock hammer; an irate Norton throws a stone through it.
Q 05Which gangster left an Indiana jail in 1934 brandishing a gun reportedly carved from wood?
John Dillinger
John Dillinger walked out of the Lake County jail at Crown Point, Indiana, on 3 March 1934 with a fake pistol, taking inmate Herbert Youngblood, who was shot dead by police in Michigan two weeks later.
Q 06Which inmate broke out of Alcatraz on 11 June 1962 with brothers John and Clarence Anglin?
Frank Morris
A fourth man, Allen West, could not get out of his cell in time and was left behind. No conclusive evidence about the fate of the three who got away has ever surfaced.
Q 07Alcatraz Federal Penitentiary sat on an island in which body of water?
San Francisco Bay
Alcatraz sits on a rocky island in San Francisco Bay, about 2 km from the city shore; the cold, fast-moving water was long held up as the reason nobody could swim away.
Q 08Which prison saw the UK's biggest peacetime jailbreak, when 38 republican prisoners escaped H-Block 7 in 1983?
The Maze
The Maze, the Long Kesh complex outside Lisburn, lost 38 IRA prisoners on 25 September 1983 after they seized H-Block 7 with smuggled handguns; one prison officer died of a heart attack.
Q 09Which German castle housed Oflag IV-C, the WWII camp for Allied officers who had already escaped other camps?
Colditz
Colditz Castle in Saxony held Oflag IV-C; its first British inmates, the Laufen Six, arrived in November 1940 after an escape attempt from Oflag VII-C at Laufen.
Q 10What did the 1962 Alcatraz escapees tuck into their beds to fool the night count?
Papier-mâché heads
Papier-mâché heads, built from soap, toilet paper and plaster, painted flesh-coloured and topped with hair from the barbershop floor, lay on the pillows while the men slipped out through widened vents.
Q 11In what year did the FBI conclude the 1962 Alcatraz escapees had most likely drowned?
1979
The FBI closed its case on 31 December 1979, concluding Morris and the Anglin brothers had most likely drowned in the bay, while the US Marshals Service kept its own warrants active.
Q 12How many escape attempts were made from Alcatraz during its 29 years as a federal penitentiary?
14
Alcatraz recorded 14 escape attempts involving 36 prisoners, two of them trying twice, between its opening as a federal prison in 1934 and its closure in March 1963.
Q 13What were the three tunnels of the 1944 Great Escape from Stalag Luft III called?
Tom, Dick and Harry
Q 21In Papillon, Henri Charrière claims he finally escaped the penal colony in 1941 on a raft made of what?
A bag of coconuts
In Papillon he floats off Devil's Island on a bag of coconuts lashed into a raft and rides the swell to the mainland; French records suggest Charrière was never actually held on Devil's Island.
Q 22What did prisoners secretly build in the attic of Colditz Castle in the winter of 1944–45?
A glider
The two-seat glider nicknamed the Colditz Cock was built from bed slats and cotton sheets behind a false wall in the attic; the camp was liberated in April 1945 before it could be launched.
Q 23The 1864 Libby Prison escape saw 109 Union officers tunnel out of a prison in which city?
Richmond
The tunnels Tom, Dick and Harry started under huts 123, 122 and 104; guards found Tom, Dick became a store for spoil, and Harry carried the March 1944 breakout.
Q 14How many prisoners got out through the tunnel before the Great Escape was discovered?
76
The plan had been for 220; only three reached safety, and Hitler had fifty of the recaptured men executed.
Q 15How many of the recaptured Great Escape officers were shot on Hitler's orders in 1944?
Fifty
Fifty were executed singly or in pairs; Göring and Keitel talked Hitler out of shooting all of them, fearing reprisals against German pilots held by the Allies.
Q 16Which Stalag Luft III veteran wrote the 1950 book behind the 1963 film The Great Escape?
Paul Brickhill
Paul Brickhill, an Australian Spitfire pilot held at Stalag Luft III, published The Great Escape in 1950; the 1963 film added inventions such as Steve McQueen's motorcycle jump.
Q 17A 1943 Stalag Luft III escape that hid a tunnel under gymnastics equipment inspired which 1950 film?
The Wooden Horse
The Wooden Horse (1950) dramatised the October 1943 break by Codner, Williams and Philpot, who dug about 30 metres in three months beneath a vaulting horse, scooping sand with bowls.
Q 18How did Richard Matt and David Sweat break out of the Clinton Correctional Facility in 2015?
A cut steam pipe into the sewer
Matt and Sweat cut through their cell walls, then cut into a steam pipe and crawled along it to a sewer manhole outside the walls; Joyce Mitchell, meant to drive them away, never showed.
Q 19How did Ted Bundy make his first escape, from a courthouse in Aspen in June 1977?
Jumped from a second-storey window
Bundy asked to visit the courthouse law library during a recess, then jumped from its second-storey window; he hurt an ankle landing and was caught six days later in Aspen.
Q 20For his second escape, Bundy sawed through the ceiling of his cell and dropped into whose apartment?
The chief jailer's
He crawled through the ceiling space and dropped into the chief jailer's apartment, empty while the jailer was out for the evening; he changed into clothes from the closet and walked out the front door.
They dug from a rat-infested cellar the guards refused to enter, and over half reached Union lines.
Q 24The Texas Seven, who broke out of the Connally Unit in 2000, were caught thanks to which TV show?
America's Most Wanted
Six were arrested in Colorado within days of the January 2001 broadcast; the seventh shot himself rather than be captured.
Q 25Ronnie Biggs escaped Wandsworth Prison in 1965 by scaling the wall and dropping onto what?
A removal van
Biggs went over the wall on a rope ladder and dropped onto the roof of a removal van parked outside, 15 months into a 30-year sentence; he stayed free for 36 years, mostly in Brazil.
Q 26Serial escapee Yoshie Shiratori rusted his handcuffs at Abashiri Prison using what?
Miso soup
Shiratori spat miso soup onto his handcuffs and the cell door's inspection hatch night after night until the metal corroded; in August 1944 he slipped the cuffs and squeezed out through the hatch.
Q 27How many times did London thief Jack Sheppard escape from prison in 1724 before being hanged at Tyburn?
Four
Sheppard escaped four times in 1724, from St Giles's Roundhouse, the New Prison at Clerkenwell and twice from Newgate, before being hanged at Tyburn that November aged 22.
Q 28Casanova escaped in 1756 from 'the Leads', a prison in the roof of which Venetian building?
The Doge's Palace
The Leads were cells under the lead roof of the Doge's Palace; Casanova and the priest Balbi broke through the roof plates on the night of 31 October 1756 and talked their way out at dawn.
Q 29James Earl Ray escaped Missouri State Penitentiary in 1967 hiding in a truck carrying what?
Bread
Ray hid in a crate beneath loaves in a bread truck leaving the prison bakery on 23 April 1967; a year later he shot Martin Luther King Jr. in Memphis.
Q 30Serial escapee Steven Jay Russell of I Love You Phillip Morris was sentenced to how many years in total?
144
Russell's sentences add up to 144 years, 99 of them for his escapes alone; Jim Carrey played him opposite Ewan McGregor in I Love You Phillip Morris (2009).