[Hale's Guide] Our 25 Best Riddles for Dungeons and Dragons (2024)

Riddle me this...

Well, if you didn't guess it based on the subject of this post then I think maybe there is no hope for you. It's a riddle!

Preparing for a session can take a load of time. Riddles are a great way to challenge your players without any extra preparation from you. Depending on how hard the riddle is, you might create 30 minutes of engaged head scratching by your players.

Dungeons and Dragons is replete with troublesome Trolls and worrying Wizards. While your party might have the tendency murder-hobo their way through an encounter, a riddle can stop them in their tracks and make them think!

So, here are 25 great riddles to spice up your Dungeons and Dragons campaign.

Riddle #25

"What always runs but never walks.

Often murmurs, never talks.

Has a bed but never sleeps.

An open mouth that never eats?"

I love this riddle. It's really challenging if you haven't heard it before but is totally logical. So when you get it the penny drops in a satisfying way. The answer is an element of nature so it would fit in great for a fantasy or historical setting. You could have it asked by an aquatic creature ask the question to allow the part to ford a river or even have it inscribed on a door and, when the party get the answer, the door opens only to release a torrent of water which has been held back. The answer for this riddle is a river.

Riddle #24

"I don’t have eyes,

But once I did see.

I once had thoughts,

Now white and empty."

This one is a little morbid (literally). But that might make it perfect for a more creepy campaign setting or session. Or perhaps just in a Shakepeare-esk "Alas, poor Yorick, I knew him, Horatio.” kind of scene. Depending how literary inclined you and your party might be. Or in true Dungeons and Dragons style, a dragon could use the riddle to toy with the party all while lounging atop a pile of the bones of his previous would-be vanquishers. A skull is the answer and many are the ways which you could weave it into a fantasy campaign.

Riddle #23

"Bright as diamonds,

Loud as thunder,

Never still,

A thing of wonder."

The subject of this riddle has always been fixating to many people over the ages. Part of many mythologies and legends. I'veoften wondered what it is about it which resonates sointrinsically with us that people willpilgrimagehundreds of miles just to look at it. Needless to say that the answer to this riddle, a waterfall, can easily be tied into a non-combat encounter toadd some mythological depth to your session and get your players brains ticking.

Riddle #22

"My life can be measured in hours,

I only servetobe devoured.

Slim, I am quick.

Fat, I am slow.

Wind is my foe."

You can hear the water droplets rhythmically hitting the ground as you and your partycontinue into the cave. As you leave warmth of daylight for the cold embrace of the Underdark, a thick darkness surrounds you and your adventuring fellows. Suddenly, all of your light sources snuff out and a women's voice whispers a riddle.

Thegroup readies itself for an attack but before it comes a party member blurts out "A candle!" Instantly, a single candle lights revealing the face of your questioner.

Riddle #21

What is it that given one,

you’ll have either two or none?

You delve ever more deeply intothe catacombs, following the winding and pressing corridors into the deepest bowls of the city.

Squeezing through an especially narrow bottle neck, you and your party find yourself in a room which splits off into many tunnels and passages.

In typical fashion, the bard pipes up first: "Well, this is great. How the hell are we supposed to know where to go now?"

Not a moment later a cold pressure rolled into the room and a billowing voice echoes oppressivelyaround the room: "Foolish children, you have come this far but you do not know 'What is it that given one, you'll have either two or none?' Answer meor have this room beyour grave."

You all exchange puzzled looks, trying to figure out the answer. The rolling echoes of the voice grows quieter, but its words linger in your mind.

With as little hesitation as humanly possible, the bard once again about burst "A choice!"

The walls rumble and the room becomes hazy with the dust of untouched decades, and within the blink of an eye the multitude of corridors move, begin to merge and fully join into a single passageway forward.

Riddle #20

If you drop me, I’m sure to crack.

Give me a smile, and I’ll always smile back.

~ A mirror

Riddle #19

Never resting, never still.

Moving silently from hill to hill.

It does not walk, run or trot.

All is cool where it is not.

~ Sunshine

Riddle #18

A father’s child,

a mother’s child,

yet no one’s son.

Who am I?

~ The daughter

Riddle #17

What has cities, but no houses;

forests, but no trees;

and water, but no fish?

~ A map

Riddle #16

Pronounced as one letter,

And written with three,

Two letters there are,

And two only in me.

I’m double, I’m single, I’m black, blue, and grey,

I’m read from both ends,

And the same either way.

~ Eye

Riddle #15

The cost of making only the maker knows,

Valueless if bought, but sometimes traded.

A poor man may give one as easily as a king.

When one is broken pain and deceit are assured.

~ A Promise

Riddle #14

I am born in fear,

raised in truth,

and I come to my own in deed.

When comes a time that I’m called forth,

I come to serve the cause of need.

~ Courage

Riddle #13

What falls but never breaks? What breaks but never falls?

~ Night and Day

Riddle #12

What goes through a door but never goes in or comes out?

~ A keyhole

Riddle #11

What does man love more than life

Fear more than death or mortal strife

What the poor have, the rich lack, and what contented men desire,

What the miser spends and the spendthrift saves

And all men carry to their graves?

~ Nothing

Riddle #10

Three lives have I.

Gentle enough to soothe the skin,

Light enough to caress the sky,

Hard enough to crack rocks.

~ I am Water

Riddle #9

Often held but never touched,

always wet but never rusts,

often bites but seldom bit,

to use me well you must have wit.

~ Tongue

Riddle #8

What is it that you ought to keep after you have given it to someone else?

~ Your word

Riddle #7

Man walks over, man walks under, in times of war he burns asunder.

~ A bridge

Riddle #6

Five hundred begins it, five hundred ends it,

Five in the middle is seen;

First of all letter, the first of all numbers, Take up their stations between.

Join all together, and then you will bring

Before you the name of an eminent king.

~ DAVID (Roman numerals)

Riddle #5

You saw me where I never was and where I could not be. And yet within that very place, my face you often see.

~ A reflection

Riddle #4

One by one we fall from heaven down into the depths of past,

And our world is ever upturned so that yet some time we’ll last.

~ Sands in an hourglass

Riddle #3

Alive without breath,

As cold as death,

Clad in mail never clinking,

Never thirsty, ever drinking

~ A fish

Riddle #2

I go around in circles,

But always straight ahead

Never complain,

No matter where I am led.

~ Wheel

Riddle #1

A thousand coloured folds stretch toward the sky,

Atop a tender strand,

Rising from the land,

‘Til killed by maiden’s hand,

Perhaps a token of love, perhaps to say goodbye.

~ A Flower

Well, that's our top 25 riddles for D&D. We hope these prove useful in enhancing your sessions and bringing some new challenges to your sessions.

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