Prisons
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50 free Prisons trivia questions with answers — history quiz, new questions added Oct 2026.
Prisons hold a strange place in the imagination. Most people will never see the inside of one, yet almost everyone can name a few, and the stories that come out of them are some of the best in history: impossible breakouts, celebrity inmates, reforms that went wrong. Alcatraz alone has filled a shelf of books and films. This quiz starts with the famous American penitentiaries and county jails, then travels to fortress prisons, penal colonies and prisoner-of-war camps overseas. You will meet gangsters, writers and political prisoners who did time, the people who got out the hard way, the ideas that shaped how prisons are built and run, and the prisons of novels, songs and the screen. It is written for curious general players, true crime and history fans, and anyone hosting a trivia night. Every answer comes with a short explanation, so you learn the story behind each cell door.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which gym machine did English engineer William Cubitt introduce in 1818 as hard labor for convicts?
Treadmill
The treadmill began after Cubitt saw idle inmates at Bury St Edmunds jail. Convicts climbed its turning steps like an endless staircase, and an 1865 law made it standard hard labor.
Q 02Where off the coast of Cape Town did Nelson Mandela spend 18 of his 27 years as a prisoner?
Robben Island
Robben Island later sent two more former inmates to South Africa's presidency, Kgalema Motlanthe and Jacob Zuma. Before apartheid it had served as a leper colony.
Q 03Which California prison, the subject of a 1955 Johnny Cash song, hosted his 1968 live album?
Folsom
Folsom hosted two shows on January 13, 1968, with June Carter and Carl Perkins backing Cash. The album reached number one on the country chart despite little promotion.
Q 04Which 1994 film shot most of its scenes at the Ohio State Reformatory, closed four years earlier?
The Shawshank Redemption
The Shawshank Redemption made the reformatory famous, and fans gathered there for a 30th anniversary celebration in 2024. The prison itself was built between 1886 and 1910.
Q 05Which gangster jailed for tax evasion played banjo in the Rock Islanders, an Alcatraz inmate band?
Al Capone
Al Capone earned his place in the band through good behavior, and it gave Sunday concerts for other inmates. He had arrived on the island in 1934.
Q 06Where did Britain send about 162,000 convicts, beginning with the First Fleet's arrival in 1788?
Australia
Australia took mostly petty offenders: thieves made up about 80% of those transported. The last convict ship reached Western Australia in 1868.
Q 07In Les Misérables, what did Jean Valjean steal that led to nineteen years as a convict?
A loaf of bread
A loaf of bread, taken through a baker's broken window to feed his sister's starving children, put Valjean in chains. Failed breakouts stretched the sentence to nineteen years.
Q 08Which New York prison on the Hudson gave rise to the phrase 'up the river' for being sent to jail?
Sing Sing
Sing Sing sits about 30 miles up the Hudson from Midtown Manhattan, where city courts sentenced their convicts. Inmates quarried marble on the site to build it.
Q 09Which fortress held Anne Boleyn before her 1536 beheading and Hitler's deputy Rudolf Hess in 1941?
Tower of London
The Tower of London also saw its last execution in 1941, when German spy Josef Jakobs was shot there. Hess was the last state prisoner held in the castle.
Q 10Which lifestyle mogul served five months at a federal prison camp in Alderson, West Virginia?
Martha Stewart
Martha Stewart had asked to serve her time in Connecticut or Florida but was assigned to Alderson. She was convicted of making false statements about a stock sale and released in March 2005.
Q 11What did Frank Morris and the Anglin brothers leave in their beds during the 1962 Alcatraz breakout?
Papier-mâché heads
Papier-mâché heads, sculpted from soap, toothpaste, concrete dust and toilet paper and topped with barbershop hair, hid their absence. The three left on a hand-stitched raft and were never found.
Q 12Which Paris fortress prison held only seven inmates when a crowd stormed it on 14 July 1789?
Bastille
The Bastille was already scheduled for demolition, and four of its seven prisoners were forgers. Lafayette later gave its key to George Washington.
Q 13In which Alabama city's jail did Martin Luther King Jr. write his famous open letter of April 1963?
Birmingham
Q 21Which Irish playwright served two years' hard labor from 1895, then wrote a ballad about Reading Gaol?
Oscar Wilde
Oscar Wilde began the poem in exile at Berneval-le-Grand in France and finished it in Naples, months after his release in May 1897.
Q 22Which novelist's father was sent to the Marshalsea debtors' prison in 1824 over a debt to a baker?
Charles Dickens
Charles Dickens was 12 and was put to work in a factory while his father was inside. He later made the Marshalsea the setting of Little Dorrit.
Q 23Which singer played convict Vince Everett in a 1957 musical whose title song topped the US charts?
Elvis Presley
Birmingham was where King began his reply in the margins of a smuggled newspaper, the one that printed eight clergymen's statement against him. He continued on scraps of writing paper.
Q 14In which Dublin jail, now a museum, were Patrick Pearse and other leaders of the 1916 Easter Rising executed?
Kilmainham
Kilmainham opened in 1796 as the New Gaol and was closed by the Irish Free State in 1924. Its yard also saw the Free State's first executions of the Irish Civil War.
Q 15Which East River island, sold to New York City in 1884 for $180,000, became home to its main jail complex?
Rikers
Rikers is named for Abraham Rycken, a Dutch settler who took possession in 1664 and whose descendants owned it until the sale. Convicts hauling in ashes for landfill then enlarged it.
Q 16What did Jeremy Bentham call his prison design in which one unseen guard could watch every inmate?
Panopticon
The Panopticon worked because inmates could never tell when they were being watched, so they behaved as if they always were. Bentham thought the plan would suit hospitals and schools too.
Q 17Which execution method was first used on murderer William Kemmler at New York's Auburn Prison in 1890?
Electric chair
The electric chair replaced hanging under a new state law, though power pioneer George Westinghouse did not want his product used that way. Kemmler's lawyer argued it was cruel and unusual.
Q 18Which Netflix series is based on Piper Kerman's memoir of thirteen months in Danbury federal prison?
Orange Is the New Black
Orange Is the New Black ran for seven seasons from 2013 and was Netflix's most-watched original as of 2016. Kerman had served time for laundering money for a drug operation.
Q 19Which future US senator was held in Hanoi's Hỏa Lò Prison after being shot down in October 1967?
John McCain
John McCain refused an early release offered ahead of men captured before him, and endured episodes of torture. He had been shot down by a missile on his 23rd bombing mission.
Q 20Which penal colony off French Guiana, open until 1953, held the wrongly convicted Captain Alfred Dreyfus?
Devil's Island
Devil's Island took its first convicts in 1852, after 3,000 prisoners volunteered to leave France's prison hulks for the new colony. It operated for a hundred years.
Elvis Presley starred in Jailhouse Rock as a convict who learns guitar behind bars and becomes a star. Its title track, by Leiber and Stoller, spent seven weeks at number one.
Q 24At which university did Philip Zimbardo run a 1971 mock prison in a psychology building basement?
Stanford
Stanford students played guards and prisoners until Zimbardo ended the study on day six. Psychologist Christina Maslach's objections and the guards' growing brutality forced the decision.
Q 25Which enclosed Venetian crossing links the Doge's Palace to the New Prison over the Rio di Palazzo?
Bridge of Sighs
The Bridge of Sighs got its English name from Lord Byron, translating the Italian. It gave prisoners a secure walk from the interrogation rooms to their cells.
Q 26In Monopoly, what dice result frees a player from Jail without paying the $50 fine or using a card?
Rolling doubles
Rolling doubles opens the cell, yet three doubles in a row on ordinary turns send a player straight to Jail. After three failed tries inside, the fine or a card is the only way out.
Q 27Which drug lord built his own prison, La Catedral, with a football pitch, jacuzzi and waterfall?
Pablo Escobar
Pablo Escobar even chose his own guards under a 1991 surrender deal with Colombia, and the place was nicknamed Hotel Escobar. He went on the run again after one year and one month.
Q 28Which 1963 Steve McQueen film is based on a mass tunnel breakout from the German camp Stalag Luft III?
The Great Escape
The Great Escape is heavily fictionalized: the tunnels really were named Tom, Dick and Harry, but only one man from the United States took part, not the three the film shows.
Q 29Which New York prison's 1971 uprising left 43 dead after Governor Nelson Rockefeller ordered it retaken?
Attica
Attica inmates held 42 staff hostage through four days of talks, but the state refused their demand for amnesty. Nearly all the deaths came from police gunfire on the final day.
Q 30Which prison, California's oldest, was established in 1852 on a point in Marin County north of San Francisco?
San Quentin
San Quentin followed the Waban, a 268-ton wooden ship anchored in the bay that served as the state's first prison in 1851. It went on to hold the largest death row in the United States.