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I like riddles that have a wordplay aspect to them:
(from Wikipedia) Athenaeus of Naucratis (fl. C. 200 AD) compiled a copious anthology of ancient Greek riddles citing some 1,250 authors under the title Epitome.
"My first, tho’ water, cures no thirst,
My next alone has soul,
And when he lives upon my first,
He then is called my whole."
Another, composed by Miranda Plowsworth herself, is this:
When my first is a task to a young girl of spirit,
And my second confines her to finish the piece,
How hard is her fate! but how great is her merit
If by taking my whole she effects her release!
--+--+--
If you want to encourage the players to dig into their campaign setting lore, you can base riddles on mythological events, as the Norse did:
I was a hostage for him
Who being brave broke faith;
Now I and my twin brother are parted forever.
Who am I?
A Golarion-specific riddle might look like this:

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I can't think of any off the top of my head right now, but I do love riddles. I was, at one point in time, developing a little adventure I called The Crypt of Illusions, and part of it was going to be some riddles that would (hopefully) be open to multiple interpretations, one of which would get your through, the other which would lead you astray and into danger.
I've still got some of the stuff, and may continue working on it at some toerh point in time.

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1 person marked this as a favorite. |

Here's a couple of original riddles I wrote for a sphinx encounter. I think these are posted somewhere else on these forums, too.
A gape, a smile, no mouth at all,
A smile, a gape again;
'Tis only in the sky you see
My brilliant, toothless grin.
The house of the king of beasts am I
Yet I make beasts of kings.
I go as summer comes; the meek
Escape the fall I bring.

LuZeke |

I haven't used that many riddles in my adventures, though I do put in smaller riddles to serve as clues on how to get through a specifik room. I prefer when there more to a riddle than just coming up with the answer.
Take this one for instance:
Cannot be seen, cannot be felt, cannot be heard, cannot be smelt. It lies behind the stars and beneath the hills.
That's a good one, but imagine that in order to solve the rooms puzzle, not only would you have to figure out the solution to the riddle, but also cast the spell whose name is the same as the answer to the riddle.
Would suck if there wasn't a spellcaster in the party though...

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What can you put in a wooden box that makes it weigh less?
Holes
What do you call your father-in-law’s only child’s mother-in-law?
Mother
Like a monarch of a tiny nation
My subjects often are quite few.
Like the brightest student in the class
In the end I get the point, I do.
Like the snake who lies upon the grass
Whose scaly coils run on and on
You’d not refer to me as tall
But might insist I am quite long.
I’m short.
A sentence.

Azure_Zero |

Here's two not bad ones from .hack in hidden in the Epitaph of Twilight
the first riddle
"What clings to you?
Bear it—you cannot.
Accept it—you cannot.
But hidden—it is from you.
Recite its name."
though I have modified the above riddle by changing the last line to be easier on some people
"What clings to you?
Bear it—you cannot.
Accept it—you cannot.
But hidden—it is from you.
What is it?"
the second riddle
"Though equally it exists before everyone's eyes,
grasp it not one person can.
Tell me—what is it?"

Calybos1 |
1 person marked this as a favorite. |
Glittering points
that downward thrust,
Sparkling spears
that never rust.
My legs are long, my legs are short;
My legs end ere my first report.
I am free for the taking all your life,
And a painful death when quelled.
I am less than nothing to feel my weight,
but will fell the strongest if held.
A spirited jig when I’m dancing bright,
Banishing all but the darkest night.
Give me food and I will live;
Give me water and I will die.
I am the black child of a white father;
A wingless bird, flying to the clouds.
I give birth to tears in eyes that meet me,
And at once on my birth I’m dissolved into air.
I come more softly than a bird,
And lovely as a flower;
I sometimes last from year to year
And sometimes but an hour.
I stop the swiftest cart or horse
And break the stoutest tree.
And yet I am afraid of fire
And children play with me.
There's someone that I'm always near,
Yet in the dark I disappear.
To this one only I am loyal,
Though in his wake I'm doomed to toil.
He feels me not (we always touch);
If I were lost, he'd not lose much.
And now I come to my surprise,
For you are he - but who am I ?
The more that there is, the less that you see.
Tremble in fear when surrounded by me.
What does man love more than life,
Hate more than death or mortal strife;
Is that which happy men desire,
The poor all have, the rich require;
The miser spends, the spendthrift saves,
And all men carry to their graves?
Lighter than what I am made of,
More of me’s hidden than seen,
I’m a tooth in the sea, the bane of the sailor,
And whiteness formed from green.
Deep, deep, they dwell below.
Spreading outward as they go.
Never needing any air.
Sometimes stretched as fine as hair.
The Moon is my father,
The Sea is my mother;
I have a million brothers,
But die when I reach land.