27 Creepy Riddles To Stump You And Spook You

Voting Rules
Vote up the dark and twisty riddles that were no match for your sleuthing.

Throughout history, people have loved challenging one another with cryptic word puzzles that encourage them to think outside their boxes to obtain a clever answer. And while all such games are engaging, mysterious riddles with eerie elements to them somehow generate an even deeper air of creepy wonder. As we use our own skills to search for clues, the hauntingly enigmatic verses tease our brains as much as they creep us out. 

Whether the riddles comprise mind-boggling wordplay or are somewhat straightforward, we can't help but want to solve them. How many can you get right?

  • 1
    1,838 VOTES

    It Follows

    Riddle: Each morning, I appear to lie at your feet. All day I will follow no matter how fast you run, yet I nearly perish in the midday sun. What am I?






    Answer: Your shadow.

    1,838 votes
  • 2
    1,933 VOTES

    A Weekend Murder Mystery

    Riddle: A man is found murdered on a Sunday morning. His wife calls the police, who question the wife and the staff, and are given the following alibis:

    The wife: I was sleeping.
    The butler: I was cleaning the closet.
    The gardener: I was picking vegetables.
    The maid: I was getting the mail.
    The cook: I was preparing breakfast.
    Who was the killer and how did the police determine who it was?






    Answer: The police took the maid into custody, as there is no mail on Sunday.

    1,933 votes
  • 3
    1,633 VOTES

    The Place You'll Never See Your Name

    Riddle: What’s the one place you can be sure you’ll never read your name?






    Answer: Your gravestone. 

    1,633 votes
  • 4
    1,575 VOTES

    The Surgeon's Son

    Riddle: A man was driving with his son in his car. They got into an accident and were in critical condition. Two ambulances from two different hospitals arrive. The man is taken to one hospital, and his son to a different one. The doctor walks into the operating room, looks at the little boy, and says, “I can’t operate on this boy. He is my son.” 

    How can this be?






    Answer: The doctor is the boy’s mother.

    1,575 votes
  • 5
    1,468 VOTES

    A Prison Cell Escape

    Riddle: Andy is put in a cell with a dirt floor and only one window. The window is too high for him to reach. The only thing in the cell is a shovel. He won’t be able to get any food or water and only has two days to escape or he’ll expire. Andy can’t dig a tunnel because it will take him much longer than two days to do it. 

    How will Andy escape from the cell?






    Answer: Andy has to use the shovel to create a pile of dirt under the window so he can climb up onto it and escape from the cell.

    1,468 votes
  • 6
    1,376 VOTES

    The Japanese Ship

    Riddle: A Japanese ship was sailing in the ocean. The captain of the ship went for a bath. He removed his ring and kept it on the table near the engine. When he returned, he found his ring was missing. The captain called all three crew members who were working around that time. He asked them what they were doing in the last 20 minutes. 

    The first crew member said: “I was checking the navigation.”

    The second crew member said: “I was intimating the people about our arrival.”

    The third crew member said: “I was correcting the side of the flag as it was upside down.”

    The captain caught the crew member who was lying. How? 







    Answer: The third crew member was lying because the Japanese flag is the same from both sides. 

    1,376 votes