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10 Riddles In Dungeons & Dragons A DM Can Use To Challenge An Experienced Party

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 that is presented to whomever or whatever is asking the riddle. Here are ten great riddles that a DM can use to challenge a party.

10 Over The River And Through The Woods

“I have towns without people, forests without trees, and rivers without water. What am I?” 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 that is 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.

9 A Costly Riddle

“I have a tail, a head, but no legs. I am probably with you now. What am I?” 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.”

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Again, the answer could be a specific coin the party is carrying; possibly even a magical coin that the party has been benefitting from. This could also be a  riddle a merchant asks before allowing the party to see his “select” merchandise.

8 The Answer Is In The Question

“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 likelihood they will get further from the right answer. Most people will start thinking of events that signal the end/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.”

7 The Eye In The Sky

“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 put in the right setting it could be quite difficult. The answer is “The Sun”; the blue face is the sky. If the DM has the party encounter multiple blue creatures before the riddle is asked this 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).

6 Troubles Are Mounting

“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.

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The answer is actually quite obvious though; it is “A Person Riding A Horse.” Again, the answer does not necessarily have to be spoken, it could need to be given in the form 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.

5 The Burning Question

“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, it is likely the players will begin thinking of less obvious answers, and will think about golems or some other form of 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.

4 Get It In Writing

“No matter is parched, no matter if rolled. No matter if magic, no matter how old.” This riddle comes from the retro PC game Eye of the Beholder 2 from Westwood Studios; a game which had many clever riddles. It is very unlikely that one of the party has played through this game and remembers this riddle.

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The answer is “Paper.” The answer could be needed to be given with an actual piece of paper – something the party may not have at the time the riddle is asked. If the party does have paper it is probably going to be a scroll held by a spellcaster. This might make this riddle very expensive to answer.

3 Fruit Of The Earth

A magic mouth appears before the party and proclaims, “To continue I must be fed the fruit of the earth, not from a tree or bush but from the ground itself. I need a cherry, and two grapes.” This riddle will certainly confound the players, and even if they discover the answer they may not be able to answer. The answer is gemstones; the cherry is a red gemstone like a ruby, and the grapes can be either two green gems like emeralds or two purple gemstones like amethysts (or combination of the two). A DM should have the party find the gems before the riddle is asked.

2 The Answer Is Not There

“The rich want it, the poor have it, and both will perish if they eat it.” This riddle comes from Baldur’s Gate 2 and is easy if the format for giving the solution is multiple choice like it is in the game. If the players must think of the answer, without having four choices to choose from it becomes a little more difficult. The answer is “Nothing”. The DM could give the party a set amount of time (using an hourglass really heightens the tension) to provide an answer in physical form. This might force the party to provide an incorrect answer/item without thinking that doing nothing is the right answer.

1 A Riddle By Any Other Name

“Passed from father to son, and shared between brothers. Its importance is unquestioned, though it is used more by others.” This riddle will probably cause the players to begin thinking of items that are commonly passed down from father to son, but it might take them a while to think of the correct answer. The answer is “A Name.” A DM might require all the party members to say their names aloud to provide a solution to this riddle. This riddle might also be used by a creature or NPC of great power to learn who is in the party, and use this information against the party in the future.

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