The Most Challenging Riddles from Around the World

Riddles from Around the World

Ever since I first saw that scene in Disney’s Alice in Wonderland where Alice pondered the Hatter’s special riddle, I’ve been fascinated by riddles in general (as well as the Mad Hatter, but that’s a story for another day!).

Alice famously repeated “Why is a raven like a writing desk” and the Hatter and the March Hare immediately thought she had gone mad (despite the Hatter having originally asked the question himself).

Riddles themselves ask a question or make a statement in a clever, and thought-provoking manner, often times to hold a mirror up to our culture. Here we’ve assembled five of the cleverest riddles from around the world for your enjoyment.

  1. Something-or-other, (From Britain):

This riddle was found in the Exter book (dated 975 AD), a manuscript that contains a large amount of religious text and poetry. Don’t let that fool you! The last part of the book consists of roughly 100 riddles, all without answers (causing scholars to heavily debate the answers). This one is as follows:

I have heard of something-or-other, growing in its nook, swelling and rising, pushing up its covering. Upon that boneless thing a cocky-minded young woman took a grip with her hands; with her apron a lord’s daughter covered the tumescent thing.

Want the Answer? Don’t read any further if you don’t. Okay, here it is! Answer: Dough

  1. Doors to Heaven and Hell, (From the United States):

There is some debate as to where this riddle originated, and how long it has been in existence, but some believe it to have been written by American philosopher Raymond Smullyan. If it sounds familiar, it probably is. There are many variations of this riddle, but the most well known one comes from the film Labyrinth. Here’s how it goes:

You’re met with a choice between two identical doors with an identical guard at each. One door leads to heaven and one door leads to hell. You can ask one guard one question and then make your choice on which door to pass through. One of the guards always tells the truth and one of them always lies. So, what question do you ask?

Want the Answer? Don’t read any further if you don’t. Okay, here it is! Answer: If I asked the other guardian which door leads to heaven, what would he tell me? (This one takes some thought… don’t be afraid to google it!)

  1. The “First” Riddle, (From Sumer – Early Southern Mesopotamia):

Riddles aren’t a new thing, as demonstrated by the ancient civilization of Sumer. Most of theirs were recorded without answers as well, but this one has become widely known. It’s not too difficult, and as a result is a favorite (especially among teachers!). Tell us if you’ve heard it before:

There is a house. One enters it blind and comes out seeing. What is it?

Want the Answer? Don’t read any further if you don’t. Okay, here it is! Answer: A school.

  1. The Cow Riddle, (From Ancient Germanic World):

This is another riddle that has been widely translated and seen numerous recreations over time. Even so, it can’t be denied as a classic. Who doesn’t love riddles involving farm animals?

Who are those twain

that on ten feet run,

three their eyes are

but only one tail?

This riddle ponder

O prince Heidrek!

Want the Answer? Don’t read any further if you don’t. Okay, here it is! Answer: You guessed it… A cow!

  1. Plato’s Riddle, (From Athens):

Of course, sometimes certain riddles just can’t be understood. Or, at least you can understand it until you know the answer! This riddle by Plato falls into that category. It’s not the most well known riddle on our list, but it definitely falls into the “worth mentioning” category, and you’ll see why.

There is a story that a man and not a man

Saw and did not see a bird and not a bird

Perched on a branch and not a branch

And hit him and did not hit him with a rock and not a rock.”

Want the Answer? Don’t read any further if you don’t. Okay, here it is! Answer: A eunuch who did not see well saw a bat perched on a reed and threw a pumice stone at him which missed. Didn’t get it? Don’t worry, neither did I!

Riddles hold significant historic value for us, and have played a huge part in our culture and history. Ancient riddles tell us quite a bit about what is important to our ancestors, and give us a look into the past. And on top of all that, they are so fun to try and figure out!

By the way, if you’re wondering about the Alice in Wonderland riddle… there was originally no answer. The author eventually came up with the following answer:

Because it can produce a few notes, tho they are very flat; and it is never put with the wrong end in front!”

With that said, come out and see if you can solve our riddles here at Clue Avenue Escape Rooms! Solve the puzzles, answer the riddles, and escape the room in only 60 minutes or less! Can you and your team do it??

Clue Avenue Escape Rooms

Looking to entertain your mind? Our Escape Room Game Is Exactly What You Need - You And Your Team Have 60 Minutes To Solve The Puzzles & Escape The Room! Great For A Night Out With Friends, A Date Night, Or Event As A Team-Building Activity - // // 760-349-6609 //

  • Dale Crawford

    OK, I don’t get #4 The Cow Riddle. Maybe I’m just stupid or maybe my brain is out of whack at 1:30 am

    1. Clue Avenue Escape Rooms

      1:30am is definitely a tough time to be doing riddles! =P

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