In Dungeons & Dragons, there are many ways a DM can challenge the party besides pitting them against ever stronger or more numerous enemies. One of the best alternative challenges is to give the party a riddle to solve in order to advance the campaign. This is often the best way to challenge an experienced party that has gotten used to winning fight after fight.
While the answer to these riddles is usually spoken, the answer can also be a physical object presented to whomever or whatever is asking the riddle. Here are great riddles that a DM can use to challenge a party.
Updated on June 2, 2023, by Jeff Drake: Dungeon Masters can never have enough riddles on hand while managing an adventure. Riddles are a great tool for DMs that want to add a little flavor to their adventure but not one they want to over-use (like traps). Giving players ample time to solve a riddle is a great way to give the party a chance to rest in the middle of a lengthy dungeon crawl. Just in case DMs using this article have already run through the riddles, this update will add five additional riddles for them to use, bringing the total to 20.
25 A Teamwork Puzzle
This isn't a riddle given to the party verbally or in written form. Rather, this riddle is one the party must solve by each member performing a task that only they can perform, or at least are best suited to perform. The object being sought could be locked behind a series of gates.
The first gate requires incredible strength to lift. The second gate is magically locked to the floor; this one might be lifted with spells. The third gate is lifted by striking a target (or object) that lies beyond the gates and requires the use of a distance weapon. The DM can add a gate for each party member, with the means to get past each best performed by a particular party member.
24 "The More That Is Here, The Less You Will See."
The answer to this riddle is "darkness." The DM can use this riddle in interesting ways. The answer might be to extinguish all light sources in a room rather than answer the riddle verbally. A statue might ask the riddle, and the answer might be to put a bag over the statue's head or blindfold the statue. This might be harder than first thought if the statue is of a beholder - and enormous.
The answer to this riddle might be a means to help the party prepare for their next fight. If this is how the riddle is used, the DM should use a foe that players don't want to look at; good examples of this type of creature are a Medusa or basilisk.
23 "If Given One, You'll Have Many Or None."
Often the simplest of riddles are the most difficult to solve. This is generally because they don't give the players a lot of information with which to solve the riddle. That's what makes riddles like this such brain-teasers; at first, it seems like the answer could be anything or nothing. The answer is "a choice."
This riddle is another that can be used as a great plot device. Upon solving the riddle, the players are given a choice to continue the quest at one of two locations - each with their own balance of risk versus reward.
22 "I Cross The River Without Moving. What Am I?"
This is a great puzzle to use if the DM wants to lead the party to a certain destination. The answer is "a bridge," and a clever DM can use the answer as a jumping-off point to the next location required by the current quest. Players will (or should) begin looking for any nearby bridge to find the next piece of the puzzle they are trying to solve.
A great bridge to use with this type of riddle-quest is Boareskyr Bridge in the Forgotten Realms. This bridge was the site of a battle between the gods Bhaal and Cyric; since then, a community has grown around the black granite bridge. Alternately, the bridge might be a bridge between realms or dimensions rather than a means to cross a river.
21 "I Possess A Father And Mother, But Am No One's Son. Even With Siblings, I Am Brother To None."
Figured it out yet? This is one of those riddles that can stump anyone. When revealed, anyone in the party that didn't know the correct answer will almost certainly feel as though they should have been able to. The answer is quite obvious if the words in the riddle are dissected.
The answer is "a daughter." To make it less obvious, the DM should have something gender-neutral ask the question. Suitable scenarios would be; a magic mouth, a creature of some kind (like a mind flayer), or even an animated statue.
20 "Time Existed Before Me, But History Can Only Begin After My Creation."
This can be a tricky riddle because many people make the mistake of assuming everything that happened before the present, and history, to be the same thing. However, history is defined as a written account of people and events of the past. Anything before the invention of "writing" is called prehistory, making writing the answer.
A good location to use a riddle like this would be a library or a sage's home. Alternatively, the answer to this riddle could include feeding a piece of parchment and a writing utensil to a magic mouth. A failed answer to this riddle might be used to send the party to the past.
19 "Some Are Cherished, Some Are Hated, And Even If Lost, They Remain With You."
For many, this riddle might be a bit obvious. The answer is "memories," and the word "cherished" kind of gives it away, especially if adventurers are given a generous amount of time to think of an answer. However, a DM can make this riddle a little more difficult by adding a short time limit.
Solving, or failing, this riddle is an opportune moment for the DM to have the player that answered the riddle remember a long-forgotten memory - one that leads to a new adventure. Conversely, the DM could have a wrong answer remove memories from the character; perhaps they lose memories of their time traveling with the party.
18 "They Arrive Every Night Whether Invited Or Not. They Can Be Seen, But Not Heard Or Touched. If One Falls, The Rest Keep Moving."
Let's get something out of the way right now: the answer to this riddle is not Underpants Gnomes, it's "the stars." Although, technically, there's absolutely nothing preventing the DM from having a gang of gnomes obsessed with underpants from asking this riddle.
Joking aside, DMs can make this riddle more difficult by having the players encounter a ghost (non-hostile for a low-level party) shortly before they are asked. This might trick the party into thinking the answer is ghosts. A good use for this riddle is to use it as a magical lock and key for a door leading to an observatory - or a secret, conveniently placed alternate exit from a dungeon.
17 "Your Mother Is An Orc. Your Father Is A Dwarf. What Are You?"
This is the perfect riddle if the DM needs to inject a little levity into the adventure; sometimes things get too serious playing D&D. Riddles like this one remind the players they are playing a game. The answer is "a dork," which should get a chuckle from the players and help make that night's play session memorable.
Answering this riddle incorrectly could include having the character's race change over time. They should be given a warning this is happening, like being told "For not knowing what you are, you must now suffer not knowing what you shall become." This is a good side adventure for the DM to throw into the mix.
16 "They Call Me The King. I Have The Eyes, Hiss, And Fangs Of A Snake, But Have No Scales Or Venom."
The answer to this riddle is "a cat" or "cats," which probably makes this an easy riddle for cat people. Cat people meaning people that own cats, not Tabaxi - just to be perfectly clear. Having a sphinx ask this riddle might be a little on the nose and make the riddle far too easy.
A yaun-ti asking this riddle, on the other hand, might trick the players into making a wrong guess. Answering the riddle might include actually procuring a cat of some type and getting it to a specific area. Fighting a dragon is easy when compared to trying to catch a wily stray cat in a crowded marketplace.
15 "I Have Towns Without People, Forests Without Trees, And Rivers Without Water."
This is a fantastic riddle whose answer is obvious once it is figured out. It is unlikely that the party will be able to quickly solve this riddle unless one of them has already heard it. The answer is “a map.” The DM could make the answer an actual map offered to the one asking the riddle, perhaps a specific map the party has been using.
The DM could give the players an actual map but have them give it up to solve the riddle. If they haven’t made a copy beforehand, this will certainly make the campaign more difficult.
14 "I Have A Tail And A Head, But No Legs. I Am Probably With You Now."
A clever party might solve this riddle after a few minutes of thought. If a DM is worried this riddle will be solved too easily, they can always make the party answer two riddles to advance. The answer is “a coin.”
Again, the answer could be a specific coin the party is carrying, possibly even a magical coin that they've been benefiting from. This could also be a riddle a merchant asks before allowing the party to see his select merchandise.
13 "What Has A Golden Head And A Golden Tail, But No Body?"
The answer is "a gold coin," and what makes this variation on the coin riddle a bit more difficult is the distracting image of glittering piles of riches. Players might get distracted by the thoughts of magical, exotic animals before considering simple like a coin.
Any adventure that might involve treasure hunting or gold of some kind could feature this riddle, or the DM could also use it to trick players into thinking gold is involved when it's really not.
12 "You Cannot Enter This Room."
Here we have a pun of sorts. It's "a mushroom." This riddle is a nice way to pretend a riddle is something else. What seems like a simple "do not enter" sign is actually a riddle where the open-ended language gives the DM a few possibilities.
It could be that something related to a mushroom is the way to safely enter the room or that there's something nearby related to mushrooms that players have to notice.
11 "I Am The Beginning Of The End, And The End Of Before."
This will certainly get the party thinking, but that’s the beauty of this riddle. The more one tries to think, the greater likelihood they will get further from the right answer. Most people will start thinking of events that signal the end or the beginning of something, like the sunrise or sunset, birth or death.
The correct answer is simple to see if the riddle is written, but if asked orally, it is harder to see the correct answer. The answer is the letter “E.” It is the last letter in the word “before” and the first letter of the word “end.”
10 "I Am An Eye Set In A Blue Face. My Gaze Feeds The World. If I Go Blind, So Does The World."
This riddle on its own might be solved too easily, but putting it in the right setting could be quite difficult. The answer is “the sun," and the blue face is the sky.
If the DM decides the party will encounter several blue creatures before the riddle is asked, it could cause some misdirection in their thinking. Perhaps this riddle ties into a puzzle of some sort that requires the party to focus the light of the sun onto a specific location somehow, like with a spyglass.
9 "The More You Leave Behind, The More You Take."
What is it? "Footsteps." This riddle could be a clever way of giving a party directions, or a warning if combined with another clue with a number, direction, or distance. This one is tougher, however, which is why the DM should structure a story around it to give the players a clue.
It could serve as a reference for a path that characters have to follow, be part of a series of clues for a ranger or rogue following someone, or fill in part of the pursuit drama of a character being followed.
8 "What Has Six Legs, But Walks On Only Four?"
With all the weird creatures that inhabit the worlds in D&D, this riddle might stump a party. They will probably start listing creatures with numerous legs like a behir, aurumvorax, or basilisk.
The answer is quite obvious though: "a person riding a horse." Again, the answer does not necessarily have to be spoken, it could need to be given in the form of a small statue of a horse and rider, or it could require the person answering the riddle to actually be on a horse at the time.
7 "What Breathes, Consumes, And Grows, But Was And Never Will Be Alive?"
This riddle has a simple answer, but it is not immediately obvious when considering it is being asked in a fantasy setting with all manner of fantastic creatures. As with the previous entry, the players will likely begin thinking of less obvious answers and think about golems or some other form of a magical construct as a possible solution.
The answer is “fire,” which needs oxygen, consumes that which it burns, and can grow if given space and sufficient flammable materials.
This riddle may cause offense if any of your players are fire elementals.
6 "What Falls But Never Breaks, And What Breaks But Never Falls?"
Here's a tough one, so make sure there's a fairly intelligent party member who can solve it. Another drawback is that it might not translate into other languages well, as it relies on two unique English expressions.
The answer is "night and day." You can't say that night breaks. Only the day can break. Night, on the other hand, doesn't break, but it falls instead. The DM might think about leaving a few clues so players can get it.