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D&D Riddles - The DM's Mega List

by Hale L. on April 06, 2021

Dungeons and Dragons is a game of imagination and strategy, and adding riddles to your session can add an extra layer of challenge for your players. As a Dungeon Master, incorporating riddles into your game can provide a fun and interactive way for players to solve puzzles and advance their quests. To help you get started, we've compiled a list of thought-provoking riddles that are sure to keep your players on their toes. So sit back, sharpen your mind, and get ready for a riddle-filled adventure!

Welcome to our D&D riddles Mega List!

Riddle #67

A word I know, six letters it contains,
Remove one letter and twelve remains.What is it?

~ Dozens

Riddle #66

It stalks the countryside with ears that can’t hear.
What is it?

~ Corn

Riddle #65

People make me,
Save me,
Change me,
Raise me.
What am I?

~ Money

Riddle #64

A precious item born of coal;
The tool with which a hole is made.
A weapon made from unwanted wood;
The beating life that lies within.
Many hands, many faces.
A full court lies inside.
Tell me what I am.

~ A Deck of Cards

Riddle #63

How can four be half of five?

~ IV - When it's written in Roman numerals

Riddle #62

I turn once, what is out will not get in.
I turn again, what is in will not get out.
What am I?

~ A Key

Riddle #61

The more there is, the less you see. What is it?

~ Darkness

Riddle #60

What can you hold in your right hand, but never in your left hand?
~Your Left Hand

Riddle #59

What is always in front of you but can never be seen?
~The Future

Riddle #58

Red when born,
Oil makes me dull.
Shiny when old,
Water makes me red.
What am I?
~A Sword

Riddle #57

It's the answer to every question you've got.
When you think you have it, you have it not.
What is it?
~Knowledge

Riddle #56

At the beginning I am nothing,
At the end I change it all.
I am the least amongst my siblings,
Yet the first to be recalled.
I am the product of everything,
But I am infinitely small.
What am I?
~0 (Zero)

Riddle #55

Three skins have we.
One of life, then one of death, then one that’s not our own.
We’re dry when we’re wet and wet when we’re dry.
Flesh with no warmth,
Bleed with no blood,
Body but no soul.
What are we?
~Grapes

Riddle #54

While at first I might be brittle,
As you work me, soft I’ll be.
Quench my thirst with dirty water,
Me unbreakable you’ll see.
Put my body not in heaven,
I’ll turn blue, then red, then white.
Though you many times will strike me,
Loyal by your side I’ll fight.
What am I?
~A Sword

Riddle #53

He who takes it doesn’t know it.
He who has it doesn’t tell.
He who makes it always hides it.
He who knows it doesn’t sell.
What is it?
~Counterfeit Money

Riddle #52

Passed from father to son,
And shared between brothers.
Its importance is unquestioned,
Though it is used more by others.
What is it?
~ Surname

Riddle #51

Today he is there to trip you up,
And he will torture you tomorrow.
Yet he is also there to ease the pain,
When you are lost in grief and sorrow.
What is he?

~ Alcohol

Riddle #50

I have lived for many ages,
but I'm no older than a month
What am I?

~ The Moon

Riddle #49

The ocean is my mother,
And my children lakes and streams.
Sometimes clothed in silver and gold,
Many still insist I’m dull.
Though I’m void of any colour,
I give life to all that’s green.

~ Clouds

Riddle #48

Four siblings born together,
Though different could not they be.
The first runs and never wearies.
The second eats and is never full.
The third drinks and is always thirsty.
The fourth sings a song so shrill.

~ Water, Fire, Earth, Wind

Riddle #47

I shine brightest in the dark.
Though I’m there I can’t be seen.
To possess me costs you nothing.
And without me you’ll lose everything.
What am I?

~ Hope

Riddle #46

The more you take, the more you leave behind.
What am I?

~ Footsteps

Riddle #45

An untiring servant it is,
Carrying loads across muddy earth.
But one thing that cannot be forced,
Is a return to the place of its birth.

~ River

Riddle #44

In the form of fork or sheet,
I hit the ground.
And if you wait a heartbeat,
You can hear my roaring sound.
What am I?

~ Lightning

Riddle #43

Found by the wise,

Lost by the weak,
Broken, not damaged,

Carried, never touched,
Sweet, not tasted,

Unique, but universal.
What am I?

~ Voice

Riddle #42

Brought to the table.

Cut and served.

Never eaten.
What am I?

~ Cards

Riddle #41 

Though I’m tender, ⁠
I’m not to be eaten.⁠
Though fresh mint, ⁠
Nor your breath to sweeten.⁠
What am I?⁠

~ Money

Riddle #40

What is so fragile even whispering its name will kill it?⁠

~ Silence

Riddle #39

You write me with five letters,
But seven I contain.
I have keys but no locks,
Keep time but no clocks.

~ Music

Riddle #38

The foolish man wastes me,
The average man spends me,
And wise man invests me,
Yet all men succumb to me.
What am I?

~ Time

Riddle #37

When you don’t need me,
you hold me close.
But when you need me,
you have to drop me.
What am I?

~ An Anchor

Riddle #36

Feed me and I will live,
give me a drink and I will die.
What am I?

~ Fire

Riddle #35

Two friends stand
And travel together,
One nearly useless
Without the other.

~ Legs

Riddle #34

What five letter long word becomes shorter when you add two letters?

~ Short

Riddle #33

Many have heard me,
yet nobody has seen me.
I never speak back unless spoken to.
What am I?

~ An Echo

Riddle #32

I have a golden head,
And a tail of gold,
But no body.
What am I?

~ A Coin

Riddle #31

I have holes on the top and bottom.
I have holes on my left and on my right.
And I have holes in the middle, yet I still hold water.
What am I?

~ A Sponge

Riddle #30

Four letters I contain,
Forward backwards I’m the same,
Upside down I have no change.
What am I?

~ NOON

Riddle #29

What can you catch but never throw?

~ Your Breath

Riddle #28

Two fathers and two sons went fishing one day.
They were there the whole day and only caught 3 fish.
One father said, that is enough for all of us, we will have one each.
How can this be possible?

~ It is a Father, Son and Grandfather.

Riddle #27

I am not alive, but I can grow;
I don’t have lungs, but air I breath;
I have no mouth, but water drowns.

~ Fire

Riddle #26

What starts with an E,
Ends with an E,
But only contains one letter?

~ Envelope

Riddle #25

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

Riddle #24

I go around in circles,
But always straight ahead
Never complain,
No matter where I am led.

~ A Wheel

Riddle #23

Alive without breath,
As cold as death,
Clad in mail never clinking,
Never thirsty, ever drinking

~ A Fish

Riddle #22

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 #21

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 #20

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 #19

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

~ A Bridge

Riddle #18

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

~ Your Word

Riddle #17

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 #16

Three lives have I.
Gentle enough to soothe the skin,
Light enough to caress the sky,
Hard enough to crack rocks.

~ Water

Riddle #15

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 #14

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

~ A Keyhole

Riddle #13

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

~ Night and Day

Riddle #12

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 #11

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 #10

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 #9

What has cities, but no houses;
Forests, but no trees;
And water, but no fish?

~ A map

Riddle #8

A Father’s child,
A Mother’s child,
Yet no one’s son.
Who am I?

~ The Daughter

Riddle #7

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 #6

If you drop me, I’m sure to crack.
Give me a smile, and I’ll always smile back.

~ A mirror

Riddle #5

What is it that given one, you’ll have either two or none?

~ A choice

Riddle #4

My life can be measured in hours,
I serve by being devoured.
Thin, I am quick.
Fat, I am slow.
Wind is my foe.
What am I?

~ A Candle

Riddle #3

Bright as diamonds,
Loud as thunder,
Never still,
A thing of wonder.

~ A Waterfall

Riddle #2

I don’t have eyes,
But once I did see.
I once had thoughts,
Now white and empty.

~ A Skull

Riddle #1

What always runs but never walks.
Often murmurs, never talks.
Has a bed but never sleeps.
An open mouth that never eats?

~ A River

We love a good riddle. If you have a favourite that you want to share feel free to drop us an email, or send us a DM on Instagram or Facebook :)


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