50 Long Riddles to Give Your Brain a Workout

Updated: Feb. 07, 2023

You need to be one smart cookie to solve these long riddles!

Get ready: These long riddles will wrack your brain

Who doesn’t love a good riddle? Whether you prefer easy riddleshard riddles, short riddles, or even trick questions, there’s just something about trying to solve these brain busters that keeps us coming back for more. Come on, is there anything better than finally solving a mind-bender we’ve been stuck on for a while?

You may consider yourself a master of riddles, but remember—you haven’t seen our list of long riddles yet. Buckle up—these riddles will get your gears turning!

Can you solve these long riddles?

1. A wealthy family lived in a big circular house. They had a maid, a butler, and a gardener. The parents were going to a party, so they tucked the younger kids into bed and kissed them goodnight and said goodbye, and kissed the older kids goodnight. When the parents came home, all the kids were gone—they had been kidnapped. The authorities ask the butler, maid, and gardener what they were doing at the time of the kidnapping. The butler says he was organizing the library, the maid says she was dusting the corners, and the gardener says he was watering the plants. Who’s lying and actually kidnapped the kids?

Answer: The maid—she said she was dusting the corners, but the family lives in a circular house, so there are no corners.

2. A farmer went to a market and bought a wolf, a goat, and a cabbage. On his way home, the farmer came to the bank of a river and rented a boat. But crossing the river by boat, the farmer could carry only himself and a single one of his purchases: the wolf, the goat, or the cabbage. If left unattended together, the wolf would eat the goat, or the goat would eat the cabbage. The farmer’s challenge was to carry himself and his purchases to the far bank of the river, leaving each purchase intact. How did he do it?

Answer: The farmer takes seven trips over—here are his steps:

  1. Take the goat over
  2. Return
  3. Take the wolf or cabbage over
  4. Return with the goat
  5. Take the cabbage or wolf over
  6. Return
  7. Take goat over

Note: The riddle doesn’t forbid the farmer from bringing a purchase back, which makes the steps above possible.

3. A woman is sitting in her hotel room and hears a knock at the door. She opens the door to see a man whom she’s never met before. He says, “I’m sorry, I have made a mistake, I thought this was my room.” He then goes down the corridor and into the elevator. The woman goes back into her room and calls security. What made the woman so suspicious of the man?

Answer: If he really thought it was his hotel room, he would have tried to open the door—not knock on it first.

4. Grandpa went for a walk, and it started raining. He forgot to bring an umbrella and didn’t have a hat. When he got home, his clothes were soaking wet, but not a hair on his head was wet. How was this possible?

Answer: Grandpa is bald.

5. You walk into a room and see a bed. On the bed, there are two dogs, five cats, a giraffe, six cows, and a goose. There are also three doves flying above the bed. How many legs are on the floor?

Answer: Six—the bed’s four legs, plus your two legs.

6. A California farmer owns a beautiful pear tree. He supplies the fruit to a nearby grocery store. The store owner calls the farmer to see how much fruit is available for him to buy. The farmer knows the main trunk has 24 branches. Each branch has exactly 12 boughs and each bough has exactly 6 twigs. Since each twig bears one piece of fruit, how many plums will the farmer be able to deliver?

Answer: None—a pear tree doesn’t grow plums.

7. A man is found unconscious in front of a store at two in the morning. His head is bleeding and there’s a brick laying next to him. When the police arrive, they carry the man to jail. Why did they arrest him?

Answer: The man was trying to rob the store. He threw a brick at the store’s bullet-proof window and it bounced back and hit him.

8. In a one-story house at the corner of the road, the bedrooms were yellow, the kitchen was orange, the living room was red, the garage was blue, the entry hall was green and the sitting room was purple. What color were the stairs?

Answer: There’s no color because there are no stairs—it’s a one-story house.

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9. My first is in chocolate but no in ham. My second is in cake and also in jam. My third at tea-time is easily found. Altogether, this is a friend who is often around. What is it?

Answer: Cat—”c” is the first letter in “chocolate,” “a” is the second letter in “cake” and “jam,” and “t” is the third letter in “tea-time.”

10. I am beautiful, up in the sky. I am magical, yet I cannot fly. To people I bring luck, and to some people, riches. The boy at my end does whatever he wishes. What am I?

Answer: A rainbow.

RELATED: 42 Tricky “What Am I?” Riddles

11. I am a five-letter word and people eat me. If you remove the first letter I become an energy form. If you remove the first two letters, I am needed to live. Scramble the last three letters and I am a drink. What word am I?

Answer: Wheat.

12. A prisoner is called to be questioned by the guards. The guards tell the prisoner: “If you tell a lie, we will hang you and if you tell the truth, we will shoot you.” What did the prisoner say to save himself?

Answer: “You will hang me.”

13. A father told his three sons he would die soon and he needed to decide which one of them to give his property to. He said, “Go to the market and buy something that is large enough to fill my bedroom, but small enough to fit in your pocket. From this, I will decide which of you is the wisest and worthy enough to inherit my land.” They all went to the market, and each came back with a different item. The father told his sons to come into his bedroom one at a time and try to fill up his bedroom with their item. The first son came in and put some pieces of cloth he bought and laid them across the room, but it barely covered the floor. The second son came in and laid some hay on the floor, but there was only enough to cover half the floor. The third son came in and showed his father what he bought. He wound up getting the property. What did the third son show his father?

Answer: A box of matches. Whenever he lit a match, it filled the room with light.

14. It spends most of its day eating white, but when it’s quick enough, it gets to eat fruit and sometimes some blue things. It’s in a dark room, where the walls are blue, it runs from a ghost that roams the halls and haunts it all the time. What is it?

Answer: Pac-Man.

15. One night, a man runs away from home. He turns left and keeps running. After some time he turns left again and keeps running. Later, he turns left one more time and runs back home—but when he gets home, he finds a man in a mask. Who was the man in the mask?

Answer: A catcher—they’re playing baseball.

16. I look flat, but I am deep. Hidden realms I shelter. Lives I take, but food I offer. At times I am beautiful. I can be calm, angry, and turbulent. I have no heart, but offer pleasure as well as death. No man can own me, yet I encompass what all men must have. What am I?

Answer: The ocean.

17. A woman named Maria was at the funeral of her mother. She met a nice young man that she had never seen before and after the service, they spent a bit of time together. Then she got busy and didn’t get his name or phone number before he left. She tried to find him, but no one knew who he was or how to contact him. A few weeks later, Maria’s older sister dies and the police suspect murder. Who killed the sister?

Answer: Maria—she hoped the man would show up at her sister’s funeral just as he had for her mother’s funeral.

18. You stand in front of two doors. A guard stands next to each door. You know the following things: one path leads to paradise, the other leads to death. You cannot distinguish between the two doors. You also know that one of the two guards always tells the truth and the other always lies. You have permission to ask one guard one question to discover which door leads to paradise. What one question would you ask to guarantee you enter the door to paradise?

Answer: Ask, “Which door would the other guard say leads to paradise?”

Next up, try solving these dark riddles that are to die for.

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19. A spy was in Canada trying to steal insider information on how to set up new Maple Syrup factories in their country. He was introduced to the operations manager of the biggest factory in Canada. However, the manager was suspicious and decided to test him with a question before he trusted him. So he asked, “What would you be sure to find in the middle of Toronto?” The spy thought fast and came up with an answer for the manager. What was his answer?

Answer: “0”—it’s the middle letter in “Toronto.”

20. There’s a girl who has a large family. She has an equal amount of brothers and sisters, but each brother only has half as many brothers and sisters. What’s the correct amount of brothers and sisters?

Answer: Four sisters and three brothers.

RELATED: 12 Math Riddles Only the Smartest Can Get Right

21. There is a basket full of hats. Three are white and two are black. Three men, Tom, Tim, and Jim, each take a hat out of the basket and put it on their heads without seeing the hat they selected or the hats the other men selected. The men arrange themselves so Tom can see Tim and Jim’s hats, Tim can see Jim’s hat, and Jim can’t see anyone’s hat. Tom is asked what color his hat is and he says he doesn’t know. Tim is asked the same question, and he also doesn’t know. Finally, Jim is asked the question, and he does know. What color is his hat?

Answer: The hat is white. If Tom doesn’t know his hat color then the other two men’s hats cannot be both black otherwise he would know his hat is white. When Tim doesn’t know his hat color either, that means Jim’s hat could not be black otherwise Tim would have to know his hat was white based on Tom’s answer.

22. If you paint a brown house white it will become a white house. If the stoplight changes from red to green, then the light is green. So, if you throw a white shirt into the Red Sea, what will it become?

Answer: Wet—the shirt won’t change color because the Red Sea isn’t actually red.

23. Consider this about a word: The first two letters signify a male, the first three letters signify a female, the first four letters signify a great, while the entire world signifies a great woman. What is the word?

Answer: Heroine.

24. Sally lives in a place where six months of the year is mild summer and the temperature drops significantly the other six months. She owns a lake where there is a small island. She wants to build a house on the island and needs to get materials there. She doesn’t have a boat, plane, or anything to transport them to the island. How does Sally solve this problem?

Answer: She waits to take the materials over during the colder months because the lake will freeze over, so she can walk over it.

25. You walk into an old horror house. It has no power or plumbing. Once inside, you see three doors. Each door has a number on it. Behind each door is a way for you to die. Behind door number one, you die by getting eaten by a lion. Behind door number two, you die by getting murdered. Behind door number three, you die by electric chair. You can’t turn back, so you have to go through a door. Which door do you go through?

Answer: Door number three—the house has no power, which means it doesn’t have electricity. Therefore, the electric chair won’t work.

26. The captain of a ship is telling you an interesting story, and then poses a question. He says, “I have traveled the oceans far and wide. One time, two of my sailors were standing on opposite sides of the ship. One was looking west and the other one east. And at the same time, they could see each other clearly. Can you tell me how that was possible?”

Answer: The sailors were standing at opposite ends of the ship, but facing one another.

27. A girl says this to her best friend: “I was born in 1955, and I celebrated my 17th birthday last weekend.” Her best friend thinks she’s lying, but she’s actually correct. How is that possible?

Answer: She was born in room 1955.

28. There once were seven dwarfs who were all brothers. They were all born two years apart. The youngest dwarf is seven years old. How old is his oldest brother?

Answer: 19 years old—if you thought the oldest was 21, you likely didn’t count the seven-year-old dwarf as one of the seven brothers.

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29. A thief enters a store and threatens the clerk, forcing her to open the safe. The clerk says, “The code for the safe is different every day, and if you hurt me you’ll never get the code.” But the thief manages to guess the code on his own. How did he do it?

Answer: The clerk already told him the code—she said it’s “different” every day.

30. You’re out on the water and see a boat filled with people. You look away for a second and look back again, but this time you don’t see a single person on the boat. Why? Hint: The boat did not sink.

Answer: All the people on the boat are in relationships.

RELATED: Love Riddles for Romantics

31. The person who makes it has no need for it. He who purchases it does not use it. The person who does use it does not know they are. What is it?

Answer: A coffin.

32. Jim and Sarah are in a long-distance relationship. Jim buys an engagement ring for Sarah and wants to mail it to her. Unfortunately, the only way to ensure the ring will be received is to place a lock on the package. Jim has locks and Sarah has locks, but neither has keys for each other’s locks. How can they make sure the ring isn’t stolen?

Answer: The ring is sent through the mail multiple times. First, Jim puts a lock on the package and sends it to Sarah. Then, Sarah places one of her locks on the package and sends it back to Jim. Then, Jim removes his lock and sends the package back to Sarah. Finally, Sarah unlocks the package and gets the ring.

33. A man is shown a portrait painting. He looks closely, then yells, “Brothers and sisters have I none, but that man’s father is my father’s son!” Who is the man in the portrait?

Answer: The man’s son.

34. There were five men at church, and it started raining while they were outside. The four that ran still got wet, but the one that was still stayed completely dry. Why did he stay dry?

Answer: He was in a coffin—the other men were at his funeral.

35. Mrs. Jones has four daughters. Each of her daughters has one brother. How many children does Mrs. Jones have?

Answer: Five—all her daughters have the same brother.

36. There was a competition where the contestants had to hold something. At the end of the event, the winner was a person who had no hands or feet. What was it that the contestants had to hold?

Answer: Their breath.

37. A man was at a carnival and went to a booth where a carny said to him, “If I write your exact weight on this piece of paper, then you have to give me $100, but if I cannot, I will pay you $100.” The man saw no scale near the booth so he agrees, thinking he’ll lie to the carny either way about his weight. However, the man ends up paying the carny $100. How did the carny win the bet?

Answer: The carny handed the man a piece of paper that said, “Your exact weight.”

38. The owner of a popular clothing store comes up with his own method of pricing items. A vest costs $8, socks cost $10, a tie costs $6, and a blouse costs $12. Using the owner’s method, how much would a pair of underwear cost?

Answer: $18—the method is charging $2 for each letter needed to spell out the clothing item.

39. Andrew’s doctor gives him three pills and tells him to take one every half hour. How much time will have passed by the time Andrew’s taken all three pills?

Answer: One hour. Andrew will take one right away, then take one a half-hour later, then take the final one a half-hour after that.

40. What does man love more than life, and hate more than death or mortal strife; that which satisfied men want; the poor have, and the rich require; the miser spends, the spendthrift saves, and all men carry to their graves?

Answer: Nothing.

RELATED: 11 of the Most Famous Riddles in History

41. A woman wants to enter an exclusive club, but she doesn’t know the password. A man walks to the door and the doorman says 12, the man says 6, and is let in. Another man walks up and the doorman says 6, the man says 3, and is let in. Thinking she’s figured it out, she walks up to the door and the doorman says 10, she says 5, and she isn’t let in. What should she have said?

Answer: Three—the code is the number of letters that are in the number the doorman says.

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42. Chef Andrea has to light the kitchen stoves to open her restaurant for the day. There are three stoves in the kitchen: A glass stove, a brick stove, and a wood stove. She only has one match. Which does she light up first?

Answer: The match.

43. Jessica is telling her friends this story and asks them to guess if it’s the truth or a lie: “There was a man sitting in a house at night that had no lights on at all. There was no lamp, no candle, and no other source of light. Yet, he sat in the house and read his book happily.” Her friends say she’s lying, but Jessica corrects them and says she’s telling the truth. Jessica’s story is true—but how?

Answer: In Jessica’s story, the man is blind and is reading braille.

44. Wednesday, Steve and Pam go to a restaurant to eat lunch. After eating lunch, they pay the bill. But Steve and Pam do not pay the bill. So…who does?

Answer: Their friend Wednesday.

45. An evil man kidnapped someone and made them take one of two pills. One was harmless, but the other was poisonous. Whichever pill the victim took, the kidnapper took the other one. The victim took their pill with water and died. The kidnapper survived. How did the kidnapper get the harmless pill?

Answer: Both pills were harmless—the poison was in the water.

46. A man is sitting in a bar when a rich man sits next to him. He turns to the rich man and says, “Did you know I know almost every song that has ever existed?”

The rich man laughs. The man then says, “I bet you all the money you have in your wallet that I can sing a genuine song with a lady’s name of your choice in it. The rich man laughs again and says, “OK, how about my daughter’s name, Jamie Armstrong-Miller?” Minutes later, the man collects his cash and the rich man goes home cashless. What song did the man sing?

Answer: Happy Birthday.

47. Consider this: Arnold Schwarzenegger has a big one. Michael J. Fox has a small one. Prince doesn’t have one. The Pope has one but never uses it. Bill Clinton has one and uses it all the time. What is it?

Answer: A surname.

48. A red house is made out of red bricks. A yellow house is made out of yellow bricks. And, a blue house is made out of blue bricks. So, what is a green house made of?

Answer: Glass

49. Two fathers and their two sons go on a fishing trip together. Each one catches a fish to take home with them. They don’t lose any fish, and yet when they get home they, only have three fish. How is this possible?

Answer: Only three people were on the fishing trip—a grandfather, his son, and his grandson.

50. One night, a woman receives a call from the police. They tell her that her husband was murdered, and she should come to the crime scene as soon as possible. The woman drops the phone, shocked, and drives 20 minutes to the crime scene. As soon as she reaches the crime scene, the police arrest her and she is convicted of murder. How do the police know she committed the crime?

Answer: The police didn’t tell her where the crime scene was, yet she already knew where to go.

Talk about some mind-bending long riddles! If you want to test your smarts further, take a stab at solving these tricky detective riddles. How many can you get right?