The

Enigma
Tome
Over 100 Riddles To Use in Your D&D Sessions
The Enigma Tome
Riddle me this…
I twist and I turn, with words that confuse,
I hide myself in various clues.

If you wish to fight me then a sore head you’ll have,

or you can follow me down a long winding path.

I am the middle of middle and also the end.

A pencil would be better for yourself to defend.

What am I?

Answer: It’s A Riddle, of course!

Well, if you didn’t guess it based on the subject of this tome, then
perhaps there’s no hope for you!

Riddles have perplexed minds for centuries, leaving even the wisest
baffled. In The Enigma Tome, you’ll find an array of riddles designed
to do just that — challenge, confuse, and engage. Riddles offer a
unique opportunity to halt the action and turn players’ attention to
problem-solving.

This tome contains 100 of the best riddles to include in your D&D
campaign, many of which have never been seen before.

P.S. This book if formatted from A to Z based on the riddles’ answer.

So, if you have a specific answer in mind already, simply find it in the
relevant location in the book.

~ Hale from The Shop of Many Things

A
A

I am something that everyone has, but no one can lose.

What am I?

Answer: Age

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?

Answer: Alcohol

When you don’t need me,

you hold me close.

But when you need me,

you have to drop me.

What am I?

Answer: An Anchor

“A” Riddles Page 3

B
B

It wears a leather coat to keep its skins in working order.

Escorts you to other realms, without a magic portal

What am I?

Answer: Book

I cross the river without moving.

What am I?

Answer: A Bridge

Man walks over, man walks under,

in times of war he burns asunder.

What am I?

Answer: A Bridge

What can you catch but never throw?

Answer: Your Breath

What grows up while growing down?

Answer: A Bird

“B” Riddles Page 4

C
C

My life can be measured in hours,

I only serve to be devoured.

Slim, I am quick.
Fat, I am slow.
Wind is my foe.

What am I?

Answer: A Candle

Tall I am young,
Short I am old,
While with life I glow,
Wind is my foe.

What am I?

Answer: A Candle

Halo of water, tongue of wood, skin of stone and long I’ve stood.
My fingers short reach to the sky, inside my heart men live and die.

What am I?

Answer: A Castle

What stands on one leg with its heart in its head?

Answer: A Cabbage

“C” Riddles Page 5

C Brought to the table.
Cut and served.
Never eaten.

What am I?

Answer: Cards

If given one, you’ll have two or none.

What am I?

Answer: A Choice

What has two hands on its face but no arms?

Answer: A Clock

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.

What am I?

Answer: A Cloud

“C” Riddles Page 6

C I fly without wings,
I cry without eyes,
massive in size.

What am I?

Answer: A Cloud

Of the earth I am born, and I grow in the ground

dig for me deep and I might be found.

What am I?

Answer: A Crystal

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.

What am I?

Answer: Courage

What is black when you buy it, red when you use it,
and white when you throw it away?

Answer: Coal

“C” Riddles Page 7

A Coin
A COIN

I have a tail of gold and a head to match

but no body to them attach.

What am I?

Answer: A Gold Coin

“A Coin” Riddles Page 8

D
D

The more that there is,

The less you will see.

What am I?

Answer: Darkness

A father’s child,
a mother’s child,
yet no one’s son.

Who am I?

Answer: The Daughter

Five hundred begins it, five hundred ends it,

Five in the middle is seen;

First of all letters, 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.

Answer: DAVID (Roman numerals)

“D” Riddles Page 9

D A curved stick and a straight twig means red sap and a snapped
trunk.

Answer: Death by Arrow

No warning of Timber could have stopped the dropping petals.

Answer: Death by Axe

A fitting cravat for a poorly chosen suit.

Who am I?

Answer: Death by Hanging

This fire is smothered best not by water or sand but by words.

Who am I?

Answer: Desire.

When is a door no longer a door?

Answer: When It’s Ajar

“D” Riddles Page 10

D 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.

Answer: A Deck of Cards

Your Mother is an Orc.

Your Father is a Dwarf.

What Are You?

Answer: A Dork

A word I know, six letters it contains,

Remove one letter and twelve remains.

What is it?

Answer: Dozens

“D” Riddles Page 11

E E

I am the beginning of the end,

and the end of before.

What am I?

Answer: The Letter E

I have a little house in which I live all alone.

It has no doors or windows, and if I want to go out I must break

through the wall.

What am I?

Answer: A Chick In An Egg.

What starts with an E,

Ends with an E,
But only contains one letter?

Answer: Envelope

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.

What am I?

Answer: Eye

“E” Riddles Page 12

E Four siblings born together,
Though more different they could not 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.

What Are We?

Answer: The Elements: Water, Fire, Earth, Wind

Many have heard me,

yet nobody has seen me.

I never speak back unless spoken to.

What am I?

Answer: An Echo

“E” Riddles Page 13

F F

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?

Answer: It’s A Father, Son and Grandfather.

I am what’s desired above of all fame and wealth.

Without me it’s assured that you’ll begin to lose your health.

I’m not a fluid dancer, but you can put me on a shelf.

What am I?

Answer: Food

The More You Take,

The More You Leave Behind.

What am I?

Answer: Footsteps

“F” Riddles Page 14

F Alive without breath,
As cold as death.

Clad in mail never clinking,

Never thirsty, ever drinking.

What am I?

Answer: A Fish

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.

What am I?

Answer: A Flower

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

Answer: The Future

“F” Riddles Page 15

Fire
FIRE

What breathes, consumes, and grows,

But was and never will be alive?

What am I?

Answer: Fire

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

What am I?

Answer: Fire

I am not alive, but I can grow;

I don’t have lungs, but air I breath;

I have no mouth, but water drowns.

Answer: Fire

“Fire” Riddles Page 16

G
G

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?

Answer: Grapes

I can bring down the mightiest of men.

Nobody can defy me.

I am the enemy of flight.

Yet you can’t even sense my presence.

What am I?

Answer: Gravity

“G” Riddles Page 17

H
H

What can you hold in your right hand,

but never in your left hand?

Answer: Your Left Hand

Six legs I have but I’m faster on four.

What am I?

Answer: A Person Riding A Horse

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?

Answer: Hope

The more you take out the bigger I get.

What am I?

Answer: A Hole

Two bodies in one, the longer I stand, the faster I run.

What am I?

Answer: Hourglass.

“H” Riddles Page 18

H 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.

What am I?

Answer: Answers: Sands In An Hourglass

“H” Riddles Page 19

k
K

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

Answer: A Keyhole

I turn once, what is out will not get in.

I turn again, what is in will not get out.

What am I?

Answer: A Key

It’s the answer to every question you’ve got.

When you think you have it, you have it not.

What is it?

Answer: Knowledge

“k” Riddles Page 20

l L

I clap without hands and strike without weapons.

I have forks but don’t eat,

I have sheets but don’t sleep.

Though you see me strike the ground,

never in anger will it be.

My bright white kiss will make a sound,

a roaring echo there will be.

What am I?

Answer: Lightning

Two friends stand and travel together,

One nearly useless without the other.

What am I?

Answer: Legs

“l” Riddles Page 21

M
M

What comes once in a minute,

twice in a moment,
but never in a thousand years?

Answer: The Letter M

I have towns without people,

forests without trees,
and rivers without water.

What am I?

Answer: A Map

Some are cherished,

Some are hated,

And even if lost,

they remain with you.

What am I?

Answer: Memories

What has four legs in the morning, two legs in the afternoon and
three legs in the evening?

Answer: A Man. When young he crawls, when grown

walks, and when old he used a cane

“M” Riddles Page 22

M A room I am but enter me you can’t.

What am I?

Answer: A Mushroom

People make me,

Save me,
Change me,
Raise me.

What am I?

Answer: Money

Though I’m tender,

I’m not to be eaten.

Though fresh mint,

Nor your breath to sweeten.

What am I?

Answer: Money

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 He?

Answer: Counterfeit Money

“M” Riddles Page 23

M If you drop me, I’m sure to crack.

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

What am I?

Answer: A Mirror

I have lived for many ages,

but I’m no older than a month

What am I?

Answer: The Moon

You write me with five letters,

But seven I contain.

I have keys but no locks,

Keep time but no clocks.

What am I?

Answer: Music

“M” Riddles Page 24

N
N

What falls but never breaks,

and what breaks but never falls?

What am I?

Answer: Night And Day

The rich want it,

The poor have it,
And both will perish if they eat it.

What Is It?

Answer: Nothing

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?

Answer: Nothing

What belongs to you, but other people use it more than you do?

Answer: Your Name

“N” Riddles Page 25

N Passed from parent to child,
and shared between siblings,
though it is used more by others.

What am I?

Answer: A Name

Four letters I contain,

Forward backwards I’m the same,
Upside down I have no change.

What am I?

Answer: NOON

“N” Riddles Page 26

O
O

Men seize it from its home, tear apart its flesh,

drink the sweet blood, then cast its skin aside.

What am I?

Answer: Orange

As I was going to St Ives I met a man with seven wives.

Each wife had seven kids.
Each kid had seven cats.
Each cat had seven kittens.

How many were going to St Ives?

Answer: One

“O” Riddles Page 27

p P

What kind of coat is always wet when you put it on?

Answer: A Coat Of Paint

I am taken from a mine, and shut up in a wooden case, from which

I am never released, and yet I am used by almost everybody.

Answer: Pencil Lead

I’m made out of five letters,

And I’m made out of seven letters;
I have keys but I don’t have locks,
I’m concerned with time, but not with clocks.

What am I?

Answer: A Piano

If you don’t keep me, I’ll break.

What am I?

Answer: A Promise

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.

What am I?

Answer: A Promise

“p” Riddles Page 28

p I am green with envy when I am placed below the sky.
I do not breathe the air you breathe but I never wonder why.

If you go and shelter me, I simply shrink and die.

The answer to this riddle is simply who am I?

Answer: A Plant

“p” Riddles Page 29

r
R

A cloud was my mother, the wind is my father, my son is the cool

stream, and my daughter is the fruit of the land.

A rainbow is my bed, the earth my final resting place.

What am I?

Answer: Rain

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

Answer: A Reflection

What always runs but never walks.

Often murmurs, never talks.

Has a bed but never sleeps.

An open mouth that never eats?

What am I?

Answer: A River

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.

What am I?

Answer: A River

“r” Riddles Page 30

r It can pierce the best armour,
And make swords crumble with a touch.

Yet for all its power, It can’t harm a club.

What am I?

Answer: Rust.

“r” Riddles Page 31

S S

I am the beginning of sorrow and the end of sickness.

There’s no happiness without me nor is there sadness.

I am always in risk, yet never in danger.

You will find me in the sun, but I am never out of darkness.

What am I?

Answer: The Letter S

I can build castles,

I can stop a flood,
I can show the time flow,
I can make people blind,
I can make others see.

What am I?

Answer: Sand

Poke your fingers in my eyes and I will open wide my jaws.

Linen cloth, quills or paper, all will split before my might.

What am I?

Answer: Shears/Scissors

“S” Riddles Page 32

S They Arrive Every Night Whether Invited Or Not.

They Can Be Seen,

But Not Heard Or Touched.

If One Falls,
The Rest Keep Moving.

What am I?

Answer: The Stars

Up and down they go and travel, but never do they move an inch.

What am I?

Answer: Stairs

I don’t have eyes,

But once I did see.

I once had thoughts,

Now white and empty.

What am I?

Answer: A Skull

Passed from father to son,

And shared between brothers.

Its importance is unquestioned,

Though it is used more by others.

What am I?

Answer: Surname
“S” Riddles Page 33
S Never resting, never still.
Moving silently from hill to hill.

It does not walk, run or trot.

All is cool where it is not.

What am I?

Answer: Sunshine

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

Answer: Short

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?

Answer: A Sponge

The more you walk on me the more we get along,

and while other may still use me, with you is where I belong.

What am I?

Answer: Shoes

“S” Riddles Page 34

Silence
SILENCE

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

Answer: Silence

Name Me, And I Die.

What am I?

Answer: Silence

“Silence” Riddles Page 35

Sword
SWORD

Red when born,

Oil makes me dull.

Shiny when old,

Water makes me red.

What am I?

Answer: A Sword

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?

Answer: A Sword

“Sword” Riddles Page 36

t T

River bridge crossing, look out for the guards.

Can you spell that without any ‘R’s?

Answer: T-H-A-T.

Forty white horses on a red hill.

They champ, they stamp, and then stand still.

What am I?

Answer: Teeth

Often held but never touched,

always wet but never rusts,
often bites but seldom bit,
to use me well you must have wit.

What am I?

Answer: Tongue

It gets wetter as it dries?

Answer: Towel

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

What am I?

Answer: Time.

“t” Riddles Page 37

t What lies down only when it dies?

Answer: A Tree

I guard precious treasures and yet my body never moves,

but I open like a book when something of yours is used.

When finally I’m gutted always feel quite blue.

I always feel so useless without the gold that I consume.

What am I?

Answer: A Treasure Chest

“t” Riddles Page 38

W
W

I go around in circles,
but always straight ahead

Never complain,
no matter where I am led.

What am I?

Answer: Wheel

What is it that you ought to keep after

you have given it to someone else?

Answer: Your Word

Time existed before me,

but history can only begin after my creation.

What am I?

Answer: Writing

I give mirth and merriment and they say I smell quite old
but I can turn a timid man into one that is quite bold.

What am I?

Answer: Wine

“W” Riddles Page 39

Water
WATER

I start out wonderful, but then begin worse.

When you come to the end of all you know, I am there.

What am I?

Answer: The letter W

Three lives have I.

Gentle enough to soothe the skin,

Light enough to caress the sky,
Hard enough to crack rocks.

What am I?

Answer: Water

Bright as diamonds,
Loud as thunder,

Never still,
A thing of wonder.

What am I?

Answer: A Waterfall

A face I do have, but see I do not.

When they see my hands, they oft ponder in thought.

Answer: A Watch

“Water” Riddles Page 40

Z Z

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?

Answer: Zero

If I’m in front I don’t matter,

If I’m in back I make everything be more,
I am something yet I am nothing.

What am I?

Answer: Zero

“Z” Riddles Page 41

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