Jail and prison riddles provide an interesting way to challenge your mind and think about the justice system. Solving riddles can be an entertaining way to pass time and exercise your brain. Here are 85 riddles about jail with answers to ponder.
Easy Jail Riddles
Riddle 1
I have keys but no locks. I have space but no room. You can enter but can’t go outside. What am I?
Answer: A keyboard.
Riddle 2
What has hands but can’t clap?
Answer: A clock.
Riddle 3
What gets wetter the more it dries?
Answer: A towel.
Riddle 4
What has a neck but no head?
Answer: A bottle.
Riddle 5
What goes up but never comes down?
Answer: Your age.
Medium Jail Riddles
Riddle 1
A prison guard stands in front of two doors, one leading to freedom and one to a bottomless pit. Two prisoners approach and ask what lies behind each door. The guard knows where each door leads but always lies. What one question can the prisoners ask to determine the door to freedom?
Answer: They should ask “If I asked you which door leads to freedom, what would you say?” The guard will point to the wrong door.
Riddle 2
A prison warden gives an inmate a chance for parole. He places 3 marbles (1 blue, 1 red, and 1 green) into a closed bag and asks the inmate to pick out 1 marble. If he picks the blue marble, he gets parole. If he picks red or green, he has to stay. What strategy allows him the best chance of gaining parole?
Answer: The inmate should pick out 2 marbles and hold them concealed in his hand. Then he returns the remaining marble to the warden without looking at it. At least one of the marbles in his hand must be either red or green, so the marble remaining in the bag must be blue.
Riddle 3
A prisoner is trapped in a cell with no windows and no doors. The only thing in the cell is a shovel. How does he plan to escape from the cell?
Answer: He plans to dig a tunnel out using the shovel.
Riddle 4
A warden gives an inmate a chance to escape by placing 2 cards face down in front of him. One card is an ‘Escape’ card, the other is a ‘Remain Imprisoned’ card. The inmate may flip over 1 card to determine his fate. The warden knows which card is which though. What strategy can the inmate use to maximize his chances of selecting the Escape card?
Answer: The inmate can ask the warden which card they would pick if their roles were reversed. The warden will point to the Remain Imprisoned card. The inmate should then pick the other card.
Riddle 5
Three inmates stand side-by-side, randomly ordered. Each has either a red, blue or green hat on their head. They are shown to each other, but not themselves. Each must guess their own hat color. They speak simultaneously on a count of 3. The first inmate says “I don’t know”. The second inmate says “I don’t know either”. The third inmate says “My hat is green”. Which color hat is each inmate wearing and how do they know?
Answer: The first inmate is wearing red. If they saw two green hats, they would have known their hat was red. The second inmate saw a red hat and green hat, so did not have enough information to deduce their hat color. The third inmate saw one red and one blue hat, so by process of elimination knew their hat must be green.
Hard Jail Riddles
Riddle 1
A prisoner is sentenced to death and forced to choose between 3 rooms: one is full of raging fires, one is full of assassins with loaded guns, and one has lions that haven’t eaten in years. Which room is safest for him?
Answer: The room with the lions. Lions that haven’t eaten in years would be dead.
Riddle 2
A prison warden tells a prisoner if he can answer this riddle, he is free to go: “Brothers and sisters I have none but this man’s father is my father’s son.” Who is the man in relation to the warden?
Answer: The prisoner is the warden’s son.
Riddle 3
Two inmates are locked in a cell with a shovel. One inmate tries to dig a tunnel to escape while the other tries to stop him by filling in the tunnel. In the morning, they are still inside the locked cell. What happened?
Answer: They are actually just one inmate with a split personality disorder imagining themselves as two different people.
Riddle 4
An inmate is trapped in a windowless, locked room with only a bed, a calendar and a mirror inside. With no visible way to escape, how does he plan to get out?
Answer: He looks in the mirror, sees what he saw, takes the saw and cuts the bed in half, two halves make a whole, crawls out the hole.
Riddle 5
Two inmates are locked in a cell with nothing but sand. They plan to escape by having one inmate make the sand into something and hide inside it while the other inmate covers him with more sand. In the morning when the prison guard unlocks the door, only sand is left in the cell. What did they make and how did they escape?
Answer: The inmates made sand into hourglasses. When the sand ran out, they were able to escape through the hourglass’s narrow midpoint that the prison guard did not notice.
Conclusion
Riddles about jail require you to think unconventionally and from different perspectives. They challenge your assumptions and often have witty or unexpected answers. Solving these riddles can help build critical thinking, logic and problem solving skills. Next time you have a free moment, trying coming up with your own riddle about escape, imprisonment and freedom!
