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Challenging Riddles:  Riddles are a perfect way to pass the time while engaging your brain. Riddles are a perfect mix of humour, reasoning, and wordplay to puzzle the mind and bring curiosity in life. Here is a list of more than 50 challenging riddles that are perfect to make you think, find the answers, and offer a good time for fun and entertainment. These riddles are perfect for an experienced riddle solver or for a curious person. The list of challenging riddles below is a perfect mix of reasoning, humour and out-of-the-box answers that will keep you guessing.

50+ Challenging And Long Riddles To Test Your Intelligence With Answers:

1. What room can no one enter?
Answer: A mushroom.

2. A rooster lays an egg on top of a barn roof. Which way does it roll?
Answer: Roosters don't lay eggs.

3. What animal can jump higher than a house?
Answer: Any animal, because houses can't jump.

4. Before Mount Everest was discovered, what was the highest mountain on Earth?
Answer: Mount Everest—it existed before being discovered.

5. David's father has three sons: Snap, Crackle, and who?
Answer: David.

6. I'm tall when I'm young and short when I'm old. What am I?
Answer: A candle.

7. What can go around the world but stay in a corner?
Answer: A postage stamp.

8. You have a ball with nothing attached to it, you have no one to throw it back to, and nothing to bounce it off of. How can you throw the ball as hard as you can and always have it come back to you?
Answer: Throw it straight up.

9. What can run but never walks, has a mouth but never talks, has a head but never weeps, has a bed but never sleeps?
Answer: A river.

10. Two babies are born to the same mother, on the same day, of the same year, within minutes of one another. They're not twins. Why not?
Answer: They're triplets.

11. What has four fingers and a thumb, but is not living?
Answer: A glove.

12. I can only live where there is light, but I die if the light shines on me. What am I?
Answer: A shadow.

13. What has 18 legs and catches flies?
Answer: A baseball team.

14. What building has the most stories?
Answer: The library.

15. What flies when it's born, lies when it's alive, and runs when it's dead?
Answer: A snowflake.

16. Give me food, and I will live. Give me water, and I will die. What am I?
Answer: Fire.

17. I am a mother and a father, but have never given birth. I'm rarely still, but I never wander. What am I?
Answer: A tree.

18. Which word in the dictionary is spelt incorrectly?
Answer: Incorrectly.

19. What has roots that nobody sees, is taller than trees, and yet never grows?
Answer: A mountain.

20. What has only two words but thousands of letters?
Answer: The post office.

21. What has hands but can't clap?
Answer: A clock.

Also Read: 40+ What Comes First Quizzes With Answers For Kids

22. What has many teeth but can't bite?
Answer: A comb.

23. What is so fragile that just saying its name breaks it?
Answer: Silence.

24. Who can shave 25 times a day but still have a beard?
Answer: A barber.

25. I know a word of three letters. Add two or fewer, and there will be.
Answer: The word “few”.

26. What is harder to catch the faster you run?
Answer: Your breath.

27. Every night I’m told what to do, and each morning I do what I’m told. But I still don’t escape your scold. What am I?
Answer: An alarm clock.

28. What gets wet while drying?
Answer: A towel.

29. I follow you all the time and copy your every move, but you can’t touch me or catch me. What am I?
Answer: Your shadow.

30. People buy me to eat, but never eat me. What am I?
Answer: Plates and cutlery.

31. I have no feet, no hands, no wings, but I climb to the sky. What am I?
Answer: Smoke.

32. The maker doesn’t want it. The buyer doesn’t use it. The user doesn’t know it. What am I?
Answer: A coffin.

33. A plane crashed off the coast of Mexico, and every single person died, yet there were two survivors. How could that happen?
Answer: The survivors were a couple.

34. There is a house. A person enters this house blind but exits it seeing. What is it?
Answer: A school.

35. What kind of coat can be put on only when wet?
Answer: A coat of paint.

36. If an electric train is travelling south, which way is the smoke going?
Answer: There’s no smoke as it’s an electric train.

37. What kind of room has no walls or corners?
Answer: A mushroom.

Also Read: 60+ Riddles For People Over 60 Years Old To Pass Their Time

38. What do the numbers 11, 69, and 88 all have in common?
Answer: They all read the same way when placed upside down.

39. I’m light as a feather, but even the world's strongest man couldn't hold me for much longer than a minute. What am I?
Answer: Breath.

40. I have cities, but no houses. I have mountains, but no trees. I have water, but no fish. What am I?
Answer: A map.

41. A woman shoots her husband, then holds him underwater for five minutes. Finally, she hangs him. But five minutes later, they enjoy a wonderful dinner together. How can this be?
Answer: She shot a photo of her husband and developed it in a dark room.

42. I only lie down once in my life—when I die. What am I?
Answer: A tree.

43. Who can finish a book without finishing a sentence?
Answer: A prisoner.

44. What ancient invention allows people to see through walls?
Answer: Windows.

45. One knight, a ninja, and a pirate were on a ship. The ship began to sink. The ninja and the pirate jumped into a lifeboat before the ship went underwater. Who died?
Answer: The knight.

46. What has ten letters and starts with gas?
Answer: Automobile.

47. A man drove from New York City to Los Angeles in four days. At the end of his trip, he discovered that one of his tyres had been punctured. How was he able to make the drive?
Answer: It was his spare tyre.

48. What can go up a chimney when down but is unable to go down a chimney when up?
Answer: An umbrella.

49. What English word retains the same pronunciation, even after you take away four of its five letters?
Answer: Queue.

50. A murderer is condemned to death, and he has the option to die in one of the following three rooms: a room full of raging fire, a room full of assassins with loaded guns, or a room full of lions who haven’t eaten in years. Which room should he choose?
Answer: The room with the lions, because if they haven’t eaten in years, then they’re already dead.

51. You’re stuck in a room with no windows, doors, or vents to use to climb out. In the room with you is a light, a mirror, and a log of wood. How do you get out?
Answer: You turn on the light and look into the mirror. In the mirror, you see what you sa,w o, take the saw and cut the log in half. From there, two halves make a (w)hole, and you can use that hole to climb out.

52. What has a head and a tail but no body?
Answer: A coin.

53. What belongs to you but is used more by others?
Answer: Your name.

54. What goes through cities and fields but never moves?
Answer: A road.

55. What has keys but can't open locks, has space but no room, and you can enter but not go inside?
Answer: A keyboard.

56. What can you break without touching it?
Answer: A promise.

57. What gets bigger the more you take away from it?
Answer: A hole.

58. What has a neck but no head?
Answer: A bottle.

59. What has one eye but cannot see?
Answer: A needle.

60. What can travel around the world while staying in the same spot?
Answer: A postage stamp.

61. What has to be broken before you can use it?
Answer: An egg.

62. What has a thumb and four fingers but is not a hand?
Answer: A glove.

63. What can you catch but not throw?
Answer: A cold.

64. What has a face and two hands but no arms or legs?
Answer: A clock.

65. What has a ring but no finger?
Answer: A telephone.

66. What has a bottom at the top?
Answer: Your legs.

67. What has a head but never cries, has a bed but never sleeps, has a mouth but never eats?
Answer: A river.

68. What has a foot on each side but no legs?
Answer: A compass.

69. What has a spine but no bones?
Answer: A book.

70. What has a mouth but can't eat, a bed but can't sleep, and runs but has no legs?
Answer: A river.

71. What has a name but no identity?
Answer: A dictionary word.

72. What has a lock but no door?
Answer: A combination lock.

73. What has a tongue but cannot talk?
Answer: A shoe.

74. What has a heart that doesn’t beat?
Answer: An artichoke.

75. What has a bank but no money?
Answer: A riverbank.

76. What has a star but no night?
Answer: A flag.

77. What has a needle but can’t sew?
Answer: A compass.

78. What has a stem but no leaves?
Answer: A wine glass.

79. What has a crown but no head?
Answer: A tooth.

80. What has a face but no eyes?
Answer: A clock.

81. What has a foot but no toes?
Answer: A snail.

82. What has a key but can’t open doors?
Answer: A piano.

83. What has a belt but no pants?
Answer: A clock.

84. What has a horn but doesn’t honk?
Answer: A rhinoceros.

85. What has a shell but no body?
Answer: A nut.

86. What has a cap but no head?
Answer: A bottle.

87. What has a blade but no hand?
Answer: A knife.
88. What has a chain but no bike?
Answer: A watch.

89. What has a face but no expression?
Answer: A clock.

90. What has a hand but no fingers?
Answer: A clock.

91. What has a mouth but no teeth?
Answer: A cave.

92. What has a nose but no face?
Answer: A teapot.

93. What has a foot but no leg?
Answer: A bed.
94. What has a heart but no organs?
Answer: A deck of cards.

95. What has a spine but no body?
Answer: A book.

96. What has a tongue but no mouth?
Answer: A shoe.

97. What has a key but no lock?
Answer: A keyboard.

98. What has a ring but no finger?
Answer: A bell.

99. What has a head but no brain?
Answer: A pin.

100. What has a bed but no sleep?
Answer: A river

Riddle solving is more than just a timepass or hobby; it is also about boosting your cognitive health, a problem-solving exercise, and an adrenaline rush from all the brainstorming and finding the right answer. We hope this list of riddles has made you think twice or more and tested your thinking and reasoning skills. These riddles are perfect to pass the time or be healthy and competitive with your friends and family, and have a fun time together. Play riddles, stay curious, and know that sometimes the right answer is in the question itself.