Long riddles tell a story before they ask a question, and the answer usually depends on a detail buried in the middle of it. They reward the kind of reader who notices that the third sentence contained an odd, specific number.

These take longer than a one-liner and are the better choice when you want a group to actually work on something together - a classroom exercise, a long journey, a team session. Several are classic logic puzzles that are best attacked with a pen.

Every riddle here has its answer and a written explanation, because with a long riddle the reasoning is most of the point.

2.HardLong Riddle

A prisoner is told: "If you tell a lie, we will hang you and if you tell the truth, we will shoot you". What did the prisoner say to save himself?

  • A."I will tell the truth."
  • B."I will tell a lie."
  • C."You will shoot me."
  • D."You will hang me."
Answer: "You will hang me."

Claiming 'You will hang me' creates an unresolvable paradox: hanging him would make the statement true (so he told the truth and should have been shot instead), while shooting him would make it a lie (so he should have been hanged instead) - so the captors can carry out neither punishment.

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3.MediumLong Riddle

A man lives on the top floor of a hotel. When he is out with a friend or out on a rainy day, he comes back, goes to the elevator, and goes to the top floor. When he goes out alone or on a sunny day, he goes half way up and walks the rest of the way up. Why?

  • A.He simply prefers the exercise of taking the stairs.
  • B.He is claustrophobic and avoids the elevator.
  • C.He always takes the stairs to save time.
  • D.He was using an umbrella or had a tall friend to push the buttons for high floors.
Answer: He was using an umbrella or had a tall friend to push the buttons for high floors.

The man is too short to reach the elevator's top-floor button alone, so he can only ride all the way up when a friend reaches it for him or he uses his umbrella to press it on a rainy day.

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8.MediumLong Riddle

I spend most of my day eating white. When I am quick enough, I get rewarded with fruit and somethings blue. In a dark room with blue walls, I run from the ghost that roam the halls. What am I?

  • A.Ms. Pac-Man
  • B.a maze runner
  • C.an arcade ghost
  • D.Pac-man
Answer: Pac-man

In the classic arcade game, Pac-Man gobbles white dots through a dark maze, earns bonus fruit, and must flee the ghosts patrolling the halls - unless a power pellet has turned them blue.

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16.MediumLong Riddle

I can be winding and I can be straight. I can be smooth and I can be rough. Sometimes both. I start out black but fade to brown the more I am used. My favorite colors are yellow and white, and I love stripes and dashed lines. What am I?

  • A.highway
  • B.path
  • C.trail
  • D.road
Answer: road

A road can curve or run straight, be smooth or rough pavement that darkens with wear, and features yellow and white painted lane markings, including stripes and dashed lines.

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19.HardLong Riddle

I heard of a wonder, of words moth-eaten. That is a strange thing, I thought, weird. That a man's song be swallowed by a worm. His blinded sentences, his bedside stand-by rustled in the night - and the robber-guest. Not one wit the wiser. For the words he had mumbled.

  • A.silverfish
  • B.moth
  • C.termite
  • D.bookworm
Answer: bookworm

This Old English riddle (the 'Moth' riddle from the Exeter Book) describes a bookworm that literally eats through a manuscript's words while its meaning goes unnoticed.

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22.EasyLong Riddle

I have been the beginning of ideas for all time, yet I am just one simple small object, the things that you can use me for can be frustrating and also I can be pretty. I have some of the most valuable thing in the world on me, yet almost everyone owns me. With me you can make anything. What am I?

  • A.pen
  • B.notebook
  • C.canvas
  • D.paper
Answer: paper

Ideas are first sketched on paper, it can frustrate you with cuts or jams yet also be beautifully decorated, and it even carries the world's most valuable commodity - printed money.

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26.MediumLong Riddle

When I am visible to you, you cannot see me, but when I am invisible, you long to see me. I am plenty with someone patient, but all the more scarce with a hasty one. I am greater than all, but still in the control of those who value my existence. Who am I?

  • A.patience
  • B.opportunity
  • C.luck
  • D.time
Answer: time

When time is passing normally you don't notice it, but once it feels like it's running out you wish you could see more of it; patient people feel they have plenty, while impatient people feel it's always scarce.

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27.EasyLong Riddle

It speaks to you, yet it can't speak. When you hold it you can travel, in your mind's eye worlds unravel. And everything in it's a lie. And with every new untruth, still you feel it speaks the truth.

  • A.novel
  • B.film
  • C.story
  • D.book
Answer: book

A book communicates without a voice, transports readers to imagined worlds through the mind's eye, and even though its story is fiction, a good one feels entirely true while you're immersed in it.

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28.MediumLong Riddle

It's round but also like a chess-board. It can and is both whirled and curled, And bent and shot and parried. Some play it on a field or watch it on the couch, And anyone can play it, even Peter Crouch.

  • A.rugby ball
  • B.basketball
  • C.volleyball
  • D.football
Answer: football

A soccer ball's black-and-white paneled pattern resembles a chessboard, and it can be whirled, curled, bent, shot, and parried by any player - even towering pros like Peter Crouch.

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33.HardLong Riddle

My first a blessing sent to earth, of plants and flowers to aid the birth; my second surely was designed to hurl destruction on mankind; my whole a pledge from pardoning heaven, of wrath appeased and crimes forgiven.

  • A.sunbeam
  • B.storm
  • C.mist
  • D.rainbow
Answer: rainbow

'Rain' nurtures plants and flowers, 'bow' (as in bow and arrow) is a weapon of destruction, and together 'rainbow' is the biblical sign of God's promise never to flood the earth again.

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38.HardLong Riddle

My head and tail both equal are, my middle slender as a bee. Whether I stand on head or heel Is quite the same to you or me. But if my head should be cut off, the matter's true, though passing strange directly I to nothing change.

  • A.zero
  • B.infinity symbol
  • C.three
  • D.eight
Answer: eight

The numeral 8 has two equal round loops joined by a slim waist, looks the same right-side up or upside-down, and if you slice off its top loop, what remains is simply a 0.

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52.MediumLong Riddle

Those wooden birds are now in sight whose voices roar, whose wings are white, whose maws are fill'd with hose and shoes, with wine, cloth, sugar, salt and news, when they have eas'd their stomachs here they cry farewell, until next year.

  • A.barges
  • B.galleons
  • C.trading vessels
  • D.ships
Answer: ships

This old riddle describes wooden sailing ships with roaring cannons, white sails ('wings'), and cargo holds ('maws') full of goods that unload at port before sailing off again.

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56.EasyLong Riddle

Creatures of power, creatures of grade, creatures of beauty, creatures of strength. As for their lives, they set everything's pace. For all things must come to live. Under their emerald embrace. Either in their life or in their death.

  • A.forests
  • B.plants
  • C.vines
  • D.trees
Answer: trees

Trees of every size and strength shelter all living things beneath their green canopy in life, and their wood often accompanies us even in death, as with a coffin.

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62.MediumLong Riddle

We are little brethren twain, arbiters of loss and gain; man to our counters run, some are made, and some undone; but men find it, to their cost, few are made, but numbers lost; though we play them tricks for ever, yet they always hope our favor.

  • A.coins
  • B.cards
  • C.dominoes
  • D.dice
Answer: dice

A pair of dice decides fortunes at the gaming table - luck rarely favors the gambler, yet players keep hoping the dice will turn in their favor.

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67.HardLong Riddle

I am the beginning of sorrow, and the end of sickness. You cannot express happiness without me, yet I am in the midst of crosses. I am always in risk, yet never in danger. You may find me in the sun, but I am never seen out of darkness.

  • A.the letter C
  • B.the letter X
  • C.the letter K
  • D.S
Answer: S

The letter S starts 'sorrow' and ends 'sickness,' sits inside 'happiness' and 'crosses,' pairs with 'risk' but not 'danger,' and appears in 'sun' but never outside 'darkness.'

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76.EasyLong Riddle

There's not a kingdom on the earth, but I have traveled over and over, and though I know not whence my birth, yet when I come, you know my roar. I through the town do take my flight, and through the fields and meadows green, and whether it be day or night, I neither am nor can be seen.

  • A.breeze
  • B.storm
  • C.gust
  • D.wind
Answer: wind

The wind has traveled everywhere without a birthplace of its own, roars audibly through town and field, yet remains completely invisible day or night.

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77.MediumLong Riddle

Within passion's fruit they will be found, and more of them in the pomegranate's crown. Rowed they are within an apple's core, yet other fruits have them more. And though the nectarine has but one, still, this is all just in fun. Playing hide and seek- a children's game. Finding out each player is just the same.

  • A.pits
  • B.kernels
  • C.pips
  • D.seeds
Answer: seeds

Passion fruit, pomegranates, apples, and nectarines all contain seeds in varying numbers, and the poem plays on "seeds" sounding just like "seeks" in hide-and-seek.

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81.HardLong Riddle

Five hundred begins it, five hundred ends it. Five in the middle is seen. First of all figures, the first of all letters. Take up their stations between. Join all together, and then you will bring before you the name of an eminent king.

  • A.Solomon
  • B.Goliath
  • C.Saul
  • D.David
Answer: David

D (500 in Roman numerals) starts and ends the name, V (5) sits in the middle, and A (first letter of the alphabet) and I (the first Roman numeral) fill the remaining spots, spelling DAVID, the biblical king.

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84.HardLong Riddle

Six letters do my name compound; Among the aged oft I'm found; The shepherd also, by the brook, Hears me when leaning on his crook; But in the middle me divide, And take the half on either side, Each backward read, a liquor tell, Ev'ry gay toper knows it well.

  • A.whisper
  • B.mutter
  • C.ripple
  • D.murmur
Answer: murmur

Split 'murmur' down the middle into 'mur' and 'mur,' and each half read backward spells 'rum' - the liquor every heavy drinker ('toper') knows well.

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87.MediumLong Riddle

I am never quite what I appear to be. Straight-forward I seem, but it's only skin deep. For mystery most often lies beneath my simple speech. Sharpen your wits, open your eyes, look beyond my exteriors, read me backwards, forwards, upside down. Think and answer the question...What am I?

  • A.puzzle
  • B.mystery
  • C.enigma
  • D.riddle
Answer: riddle

A riddle looks simple on the surface but hides a deeper meaning, rewarding those who examine it from every angle - fittingly, this very riddle describes itself.

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93.HardLong Riddle

It's true I bring serenity. And hang around the stars. But yet I live in misery, you'll find me behind bars. With thieves and villains I consort. In prison I'll be found. But I would never go to court. Unless there's more than one.

  • A.the letter Z
  • B.an apostrophe
  • C.the letter X
  • D.S
Answer: S

Adding the letter S turns 'star' into 'stars,' 'bar' into 'bars,' and 'court' into 'courts' - it only shows up when there's more than one of something, fitting every clue in the riddle.

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97.HardLong Riddle

My first is ocean but not in sea, My second in milk but not in me. My third is in three but not in throw, My fourth in vow but not in crow. My fifth is in eight but not in night, My last is in wrong and also right. My whole is praise for thoughts or men; Or women, too, or tongue or pen.

  • A.bright
  • B.witty
  • C.smart
  • D.clever
Answer: clever

Each line hides one letter of CLEVER - C from ocean, L from milk, E from three, V from vow, E from eight, R from wrong - spelling out a word of praise for sharp thinking.

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Frequently asked questions

A riddle set out as a short scenario - a man in a room, a race between animals, a crossing with a boat - where the answer depends on a detail in the story rather than on a pun.

Write down every concrete fact the story gives you, then look for the one that seemed like colour but is actually a constraint. That fact is almost always the key.