Prison Escapes
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96 free Prison Escapes trivia questions with answers — history quiz, new questions added Oct 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 96 questions correctly?
30 of 96 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
Raincoats, more than 50 of them, were stitched into a raft and life vests and the seams sealed against the prison's hot steam pipes; the design came from magazines found in the men's cells.
Q 02Which drug lord twice escaped Mexican prisons, reportedly in a laundry cart and later through a tunnel?
Joaquín "El Chapo" Guzmán
Joaquín "El Chapo" Guzmán is said to have left Puente Grande in a laundry cart in 2001; in 2015 he dropped through his cell's shower floor into a 1.5 km tunnel, where a motorcycle was later found.
Q 03Stalag Luft III, the Great Escape camp, stood at Sagan, a town now in which country?
Poland
Poland: wartime Sagan is today the Polish town of Żagań; the Germans picked the site for its sandy soil, which made tunnels prone to collapse and the bright spoil easy to spot.
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 cowed his guards with what he later said was a whittled wooden pistol, then drove the sheriff's car across the state line, a federal offence that brought the FBI into the hunt.
Q 06Which inmate broke out of Alcatraz on 11 June 1962 with brothers John and Clarence Anglin?
Frank Morris
Frank Morris, known for his intelligence, took the lead in a plan six months in the making; despite hundreds of leads, no conclusive trace of the three men 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 09Colditz Castle's wartime camp, Oflag IV-C, was reserved for which kind of Allied officer?
Repeat escapers
Repeat escapers: officers who kept breaking out of other camps were gathered in a castle the Germans thought escape-proof, and some 30 of them still made it out for good.
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 11Which agency took over the hunt for the 1962 Alcatraz escapees when the FBI closed its case in 1979?
US Marshals Service
The US Marshals Service inherited the case on 31 December 1979, when the FBI concluded the three had most likely drowned, and kept its warrants active for decades in case any of them surfaced.
Q 12What became of most of the 36 men who tried to escape Alcatraz federal prison?
They were recaptured
They were recaptured: of the 36 men, 23 were caught, six were shot dead and two drowned, while five, the 1962 trio among them, are listed as missing and presumed drowned.
Q 13What were the three tunnels of the 1944 Great Escape from Stalag Luft III called?
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 behind a false wall from bed slats and checked cotton bedding; American troops freed the camp 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
Tom, Dick and Harry
The tunnels Tom, Dick and Harry were started together; guards found Tom, Dick became a store for spoil, and Harry carried the breakout of March 1944.
Q 14Why did some 4,000 bed boards vanish from Stalag Luft III's bunks before the Great Escape?
To shore up the tunnels
To shore up the tunnels: the sandy walls were lined with bed boards, leaving some men only eight to sleep on, and 76 prisoners crawled out before a guard spotted the next man.
Q 15Which German organisation shot fifty recaptured Great Escape officers in 1944?
The Gestapo
The Gestapo drove the fifty to remote spots in ones and twos and shot them on Hitler's orders; after the war RAF investigators hunted the killers down for war-crimes trials.
Q 16Which Stalag Luft III prisoner, later author of The Dam Busters, wrote the 1950 book The Great Escape?
Paul Brickhill
Paul Brickhill, an Australian Spitfire pilot, worked for the escape organisation but was barred from the tunnel itself for fear he would panic underground and block the men behind him.
Q 17How did three prisoners hide a tunnel entrance in Stalag Luft III's open exercise yard in 1943?
Under a vaulting horse
Under a vaulting horse: diggers were carried out inside it each day and worked below while comrades vaulted overhead; all three got home to Britain, and the story became the 1950 film The Wooden Horse.
Q 18How did Richard Matt and David Sweat break out of Clinton Correctional Facility in 2015?
A cut steam pipe into the sewer
A cut steam pipe into the sewer was the way out: Matt and Sweat cut through their cell walls, followed the pipes to a manhole outside, and left a note reading 'Have a nice day'.
Q 19How did Ted Bundy make his first escape, from a courthouse in Aspen in June 1977?
Jumped from a second-storey window
Jumped from a second-storey window of the law library: representing himself in court, Bundy had been excused from shackles; he hurt his ankle in the fall and was caught six days later.
Q 20In Ted Bundy's second escape, in December 1977, he sawed through his cell ceiling 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.
Richmond, the Confederate capital, held captured Union officers in Libby, a converted warehouse; after 17 days of digging the tunnellers came up in a tobacco shed, and 59 of the 109 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
America's Most Wanted led straight to the arrests of January 2001: six of the men were caught in Colorado within days of the broadcast, and 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
A removal van waited outside as Biggs came over the wall on a rope ladder, 15 months into a 30-year sentence; he stayed free for 36 years, shielded in Brazil as the father of a Brazilian child.
Q 26Serial escapee Yoshie Shiratori is said to have rusted his handcuffs at Abashiri Prison using what?
Miso soup
Miso soup, dripped onto his handcuffs and the cell door's food slot at every meal, is said to have corroded the metal with its salt until he could break free; accounts of his four escapes vary.
Q 27Jack Sheppard broke out of which London prison twice in 1724 before he was hanged at Tyburn?
Newgate
Newgate lost him twice in 1724: the first time the slightly built Sheppard squeezed through a gap where a bar had been removed from a grille; he escaped four times in all that year.
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
Bread from the prison bakery was being trucked out on 23 April 1967, and Ray rode out hidden in the load; nearly a year later he shot Martin Luther King Jr. in Memphis.
Q 30Which comedy star played serial prison escapee Steven Jay Russell in I Love You Phillip Morris?
Jim Carrey
Jim Carrey played Russell opposite Ewan McGregor as Phillip Morris; the real Russell's four escapes earned him 99 of the 144 years he was sentenced to.