A Dungeon Master’s Guide to Riddles and Mysteries in 5e

Last Updated on January 22, 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.

Or maybe it’s thanks to the Riddle of the Sphinx – the great winged beast that barred entry to the Greek city of Thebes – posed time and again throughout the ages –  “What creature with one voice has four legs in the morning, two legs in the afternoon and three legs in the evening?”

Or maybe dungeon masters have just always been desperate for something that their players couldn’t immediately bypass with the liberal application of fireballs. 

Wherever the impulse comes from, humans have been trying to stump one another with lateral thinking puzzles since the dawn of civilization. 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? 

As a DM, riddles have the potential to be an invaluable weapon in your arsenal.

However, they’re also one of the elements of a dungeon or adventure that needs the most careful handling, as there are plenty of ways in which they can derail your game, leaving your players feeling frustrated and disengaged.

With that in mind, we’ve put together this guide to including riddles in your D&D games.

We highlight a few of the major pitfalls that you can fall into when running riddles at your table and include a few suggestions for how to minimize the danger of a tricky riddle throwing your game off track. 

Next, we’ll be taking a look at mysteries, and how you can use our framework for building riddles to construct head-scratching adventure plots. 

Last, 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. 

You can use the contents drop-down to jump straight into the example riddles or to any other section that piques your interest. Otherwise, let’s begin. 

The Problem with Riddles 

Riddles can make for a refreshing change of pace in your game of D&D. They can confound your players, encourage them to think laterally, and lead to some truly memorable ‘Ah Hah!’ moments. 

However, riddles also run the risk of frustrating your players, stalling the adventure, and generally running the momentum of your game into the ground.

I think this is largely because, unlike puzzles, traps, and monsters, a riddle only has one specific answer. Players who don’t come up with the answer can quickly get frustrated and give up.

This is especially dangerous as a DM; if your whole adventure hinges on the players solving a riddle, say, to get through a door, and your players just aren’t getting it, it won’t be long before the panic sets in. 

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) or murder the monster and 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.

The party packs up and leaves, frustrated.

You, the DM, sigh and throw your massive pile of notes that you prepared for running your Moria encounter into the garbage. Your balrog mini (definitely using the same stats as a Balor) stays in its case gathering dust. 

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 don’t solve it. 

How do we, as dungeon masters, solve this problem?

Simple… 

Riddles are for Bonus Content 

This might seem like an arbitrary ruling or even a cop-out, but the more I think about it, the more I’m convinced that – unless you are running the game for a very rare party for whom riddles are the best thing about the game – you should pretty much never put “main storyline” content behind a riddle. 

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”.

The players have fought some goblins and are on their merry way to the boss fight in the next room. 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 think this is the approach that we, as dungeon masters, should be taking with riddles. Use them as an additional seasoning for your adventures, but never (or at least, very rarely as) the main course. 

For example, in addition to using a riddle as the key to unlocking additional treasure or secrets about your world, you can also use them as an opportunity for your players to gain the advantage over their foes.

You could have your players square off against a particularly dangerous enemy, and give them a riddle that hints at its weakness.

A troll’s healing factor, for instance, is interrupted by fire damage, so have your players encounter the following riddle – perhaps scribbled in the acid-damaged journal of a deceased troll hunter. 

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.

If the players crack the riddle, they have a potent weapon in their fight against the troll. If they don’t solve it, they may still be able to bring down the troll, and might even figure out its weakness, but the fight will be significantly harder. 

You could use a riddle to give your players an escape route, access to a hidden room, an audience with a powerful ally, or any other important thing. Just be careful, however, about making their success entirely contingent on finding the right answer. 

The Anatomy of a Riddle 

In many ways, a riddle resembles a joke. The comedian John Cleese once said in an interview (that I can’t find the link for) that every joke boils down to making you assume one thing is going to happen or be said, and then subverting that expectation in some way. 

Likewise, riddles often play on this same misdirection.

Maybe they’re a bit like a magic trick as well. What good does this do us as dungeon masters, you ask?

Well, there are plenty of occasions in which you might find yourself looking to pose your own bespoke riddle to your players.

In these situations, it’s worth having a working understanding of what exactly a riddle is, lest ye end up making something that resembles the average submission to the website www.riddles.com – a deeply funny, wildly confusing hellscape of logical long jumps that must be satire. 

Let’s, for the sake of expediency, break down the riddle into three component elements: The Clues and Misdirections, the Assumption, and the Reality, using the following riddle. 

River bridge crossing, look out for the guards. Can you spell that without any ‘R’s? 

Clues and Misdirections: An evocative sentence about rivers and guards which is actually a misdirection, and a bit of wordplay which relies on recognizing the misdirection and reinterpreting the emphasis of the second sentence. 

Assumption: “Iver bidge cossing, look out fo the guads.” Absolute nonsense that should sound dumb enough that your players realize they’re being messed with. 

Reality: The first sentence is a red herring, and the players just need to spell the word That – which doesn’t have any ‘R’s in it anyway. 

Let’s try another. Now, I know this riddle was contrived by a monk in the 15th Century, but it will forever belong to Jeremy Irons in Die Hard With a Vengeance. 

“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?” 

Clues and Misdirections: This is another simple linguistic misdirection dressed up to look like a mathematical puzzle. The players are supposed to get caught up adding a man to various multiples of seven. 

Assumption: 2402 people and animals are going to St Ives. 

Reality: Only the man was going to St Ives – presumably to escape the absolute chaos of fur and screaming children waiting for him at home. 

When making your own riddles, it’s good to start with the answer first, then think of ways to express that answer in synonyms and metaphors, playing on double meanings and deploying red herrings to confuse anyone trying to solve it.

This is actually a remarkably good way of constructing mysteries as well. 

Making a Mystery

A good mystery can make for a memorable game of D&D. Some people like to base their entire campaigns around mysteries, and even DMs who prefer a more direct approach can’t resist the occasional urge to introduce them.

Essentially, mysteries present the players with a world that is not entirely as it seems, and that’s a potentially fantastic source of drama, intrigue, and a great time around the table. 

While there’s no substitute for reading, watching, and listening to as much mystery content as you can – Scooby Doo is a great start, or the works of Agatha Christie, or true crime documentaries – I once ran a mini-campaign based entirely on the first season of Orphan Black. 

Regardless of how well versed or new you are to mysteries in fiction, translating that experience to the gaming table can feel like a daunting prospect. Therefore, we’ve put together a breakdown of three techniques that can help you to craft a mystery for your campaign. 

Mysteries as Riddles 

Making mysteries is a lot like telling a riddle, or a story, or a joke. You’re setting things up to look one way (all the while drawing your audience in, directing their attention where you want it) while they’re actually very different. 

Look at this riddle which is basically a tailor-made setup for a murder mystery. 

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? 

Let’s take a look at how the building blocks of a riddle – the clues and misdirections, assumption, and reality – can help to craft our very own mystery.  

First, let’s start with the answer (the Reality) and build backward from there. 

Reality: The Mayor of the village of Rembolt and her brother the Vicar are both doppelgangers. The doppelganger who replaced the Mayor wishes to control the town in secret, but her brother wishes to go on killing unless he’s stopped. 

Now we have a crime that’s been committed, a problem to be solved, and consequences if the adventurers don’t find the killers – or, worse yet, find the wrong people. Let’s tackle the assumption next. In this case, let’s set someone up to be framed for the murders by the Mayor and the Vicar. 

Assumption: The Vicar’s loyal manservant, Pietr, is the killer. 

Now let’s lay out the clues and misdirections that the players can encounter as they search for the truth. 

Clues and Misdirections: 

Obviously, some of those events happen in order, and some may be rendered impossible by the players’ actions (no plan, puzzle, or mystery survives contact with the enemy) so you’ll probably have to improvise a little.

However, the riddle elements of clues and misdirections leading to an assumption are a great way to lay out what will happen if no one solves this mystery.

 

---

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.

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?

Throw it Out 

What is it that you keep when you need it not, but throw out when you do need it? 

Keys and Locks

I have keys but I don’t have locks; I’m concerned with time, but not with clocks. 

White Horses (from The Hobbit)

Thirty two white horses on a red hill. They champ, they stamp, and then stand still. 

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. 

Give to Keep 

What must you first give to me in order to keep it?

Rivers Without Water 

I have forests without trees, towns without people, and rivers without water. What am I? 

Golden Head 

What has a golden head and a golden tail but no body? 

The Beginning of the End… 

I am the beginning of the end, and the end of before.

Leave and Take 

The more you leave behind, the more you take.

Fall and Break 

What falls but never breaks, and what breaks but never falls?

Name and Break Me (from Baldur’s Gate 2)

Name me and so shall ye break me. 

Three Lives

Three lives have I.

Gentle enough to soothe the skin,

Light enough to caress the sky,

Hard enough to crack rocks.

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.