Last Updated on November 20, 2023
Riddles have been a quintessential part of Dungeons & Dragons since the beginning of the game.
This is probably thanks to J.R.R. Tolkien and the famous exchange of riddles in the dark between Bilbo and Gollum.
The oldest known riddle dates back to ancient Sumeria, making it potentially more than 6,000 years old.
There is a house. One enters it blind and comes out seeing. What is it?
Click For Answer
A School.
We’ve taken the liberty of putting together a list of classic riddles that you can plug straight into your campaign, or use as a template for making your own.
After the riddles, I’ll talk about a couple of tips for placement, and what the problem with riddles can be: Sometimes players fail to solve them
Example Riddles
Below, we’ve pulled together a list of our favorite riddles that you can use in your games of D&D. Just remember, don’t hide anything too important behind them.
Red or gold or blue through and through, it has no mouth but devours flesh, fat, life and limb; it fears the water but not the wind.
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Fire.
River bridge crossing, look out for the guards. Can you spell that without any ‘R’s?
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T-H-A-T
Two men drink poisoned Iced Tea. One man drinks his fast and lives. The other man drinks his slow and dies. How is this possible?
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The poison is in the ice, not the tea. The ice melts in the slower drinker’s tea.
Lighting a Fire
You are in a cold house in the winter. It is dark. You have one match.
There is a candle and there is a wood-burning stove. Which do you light first?
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The match.
Throw it Out
What is it that you keep when you need it not, but throw out when you do need it?
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An anchor.
Keys and Locks
I have keys but I don’t have locks; I’m concerned with time, but not with clocks.
Click For Answer
A piano.
White Horses (from The Hobbit)
Thirty-two white horses on a red hill. They champ, they stamp, and then stand still.
Click For Answer
Teeth.
Three Doors
There are three doors before you. Behind one is a raging fire, behind a second is a man made of stone, and behind the third are two lions who haven’t eaten in three weeks. Choose wisely.
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Lions can’t survive for three weeks without food, so that door is safe (if a little smelly).
Give to Keep
What must you first give to me in order to keep it?
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Your word.
Rivers Without Water
I have forests without trees, towns without people, and rivers without water. What am I?
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A map.
Golden Head
What has a golden head and a golden tail but no body?
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A coin.
The Beginning of the End…
I am the beginning of the end, and the end of before.
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The letter “E”.
Leave and Take
The more you leave behind, the more you take.
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Footsteps.
Fall and Break
What falls but never breaks, and what breaks but never falls?
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Night and day.
Name and Break Me (from Baldur’s Gate 2)
Name me and so shall ye break me.
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Silence.
Three Lives
Three lives have I.
Gentle enough to soothe the skin,
Light enough to caress the sky,
Hard enough to crack rocks.
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Water.
Never Was
You’ll see me where I never was and where I could not be. And yet within that very place, my face you often see.
Click For Answer
A reflection.
The Problem with Riddles
Let’s look at what is probably the best-known example of a riddle that blocks access to the rest of the adventure. We’re looking, of course, at the Doors of Durin riddle from The Fellowship of the Ring.
The fellowship comes upon a stone door that bars their access to the Mines of Moria. Moonlight reveals a glowing inscription upon the portal: “Speak friend and enter.”
This is, in theory, a near-perfect D&D encounter. There’s a riddle, a magic door, and a ticking clock in the form of the nearby Watcher in the Water ready to drag the heroes to their doom if they don’t get inside in time. Brilliant.
However, what happens if Frodo doesn’t come up with the answer? Let’s imagine you’re running this encounter for your party.
If no one figures out that the password for the door is the word friend in elvish, then they’re either going to get eaten by the tentacled lake monster (definitely an Aboleth)
Even if they defeat the monster, they remain stuck outside the tomb, growing more and more frustrated until someone suggests that maybe trying to walk over the mountains again isn’t such a bad idea.
Here we have the first problem with riddles.
Because D&D isn’t a pre-written story, there’s always going to be a chance that, when you put a riddle in front of your players, your players can’t solve it.
How do we, as dungeon masters, solve this problem?
Simple… you should pretty much never put “main storyline” content behind a riddle.
Placing Riddles in your D&D Campaign
My favorite example of riddle placement in a dungeon comes from Matt Colville’s video on building an adventure.
He makes a simple five-encounter dungeon for first-level players inside the tomb of an order of knights that’s become overrun by a handful of goblins and a bugbear.
In the first main room of the dungeon, there’s an inscription on the wall laying out the sacred vow of the order of knights.
When I ran this encounter in my game, it was:
“I give my word and swear to bring light to the darkness, hope to the fearful, and holy fire unto the heathen and the beast”.
After defeating the bugbear boss of the dungeon, if the players examine the room in greater detail, they find an inscription at the base of a statue depicting the leader of this order of knights.
The inscription reads:
“If this sacred thing you wish you take, you must give it unto me.”
It’s a riddle, the answer to which is “My word”, meaning that clever players will swear the vow written in the previous chamber.
When the oath is uttered out loud, a secret door opens behind the statue leading to the tomb where the knights are buried, and a sweet magic sword.
Note that the players don’t have to solve or even notice this riddle in order for them to have a good time in this dungeon.
They could just murder goblins and bugbears, maybe rescue the blacksmith’s son (or the local mayor in my game) and return to town triumphant. If they want to solve the riddle, however, they can take as much time as they like to do so.
I played my first tabletop RPG (Pathfinder 1e, specifically) in college. I rocked up late to the first session with an unread rulebook and a human bard called Nick Jugger. It was a rocky start but I had a blast and now, the better part of a decade later, I play, write, and write about tabletop RPGs (mostly 5e, but also PBtA, Forged in the Dark and OSR) games for a living, which is wild.
