My party is freakishly good at riddles. They love the riddles, but I need to actually give them a challenge. What is your biggest, hardest, scariest riddle?
I've shared this a thousand times, but my most successful riddle was the non-riddle riddle. You have a door with a Magic Mouth spell cast on it. Make the door as elaborate or simple as you want, whatever fits your campaign. Could also be a treasure chest, whatever. When the players approach the door, the mouth triggers and delivers a "riddle." The one I used for my campaign was an adaptation of the Sphinx riddle, something like "What walks on its feet in the morning, Swims during the day, but flies at night?" It doesn't matter what the riddle is, the only thing that matters is that it sounds plausibly solvable, and has no answer. The players will drive themselves crazy trying to solve it - my players blew through a two-hour session doing anything they could to find asolution, even after I let them scour the internet for answers.
The trick? The door is unlocked. No traps. No obstacle of any kind preventing them from just pushing the door open and walking through.
EDIT to add: If you want to add an extra layer of frustration, have the mouth repeat the riddle every time they make a guess.
There's this really fun riddle from Tales from the Yawning Portal, and it's in the 2014 Monster Manual. I've always liked it. I don't actually know how difficult it might be for your party, but it's worth mentioning here:
Round she is, yet flat as a board
Altar of the lupine lords
Jewel on black velvet, pearl in the sea
Unchanged yet ever changing, eternally
It's the moon
Rollback Post to RevisionRollBack
He doesn't have much besides the skin on his bones. Me: I'll take the skin on his bones, then.
"You see a gigantic, monstrous praying mantis burst from out of the ground. It sprays a stream of acid from it's mouth at one soldier, dissolving him instantly, then it turns and chomps another soldier in half with it's- "
This isn't really a riddle that has any actual solution, but I based a one-shot campaign around it and created a solution. The story was that an ancient wizard named Kershawnik had created a library that had been lost ages ago and is rumoured to be priceless. Many had tried to find it throughout the ages. The only clue into finding the library was this gibberish a person was saying over and over again that the party met "at random":
Near a tree by a river there's a hole in the ground, where an old man of iron goes around and around. And his mind is a beacon in the veil of the night, for a strange kind of fashion there's a wrong and right.
This is of course (most of) the chorus of a song called The Riddle by Nik Kershaw with slightly modified lyrics (Aran --> Iron). The solution was that they had to dig a hole near a tree by a river. They found a small ancient iron statue that had a joint in its waist. They had to rotate/wind the torso, so that when they let go it unwound and the head started glowing. They had to place the glowing statue into the hole with any piece of clothing at night, so that the entrance to the library was revealed.
I have a heart no surgeon finds, A throne that rules a thousand minds. Within my chest, the winters wait, And time moves slow behind my gate. Knights are my fingers, walls my skin, My moat keeps out, my halls keep in. I am the war that doesn’t roam— What am I, more fortress than home?
Roomba Knight, Architect of the Cataclysm, Foxy Lunar Archpriest. Dubbed The Fluffy Bowman by Golden. He/Him
Theatre Kid, Ravenclaw, bookworm, DM, Lego fanatic, flautist, mythology nerd, pedantic about spelling. I also love foxes, cats, otters, and red pandas!
I love K-pop Demon Hunters and Korean Mythology. If you want to ask me about something, send me a PM!
Èist ri Arirang aig BTS!
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My party is freakishly good at riddles. They love the riddles, but I need to actually give them a challenge. What is your biggest, hardest, scariest riddle?
I've shared this a thousand times, but my most successful riddle was the non-riddle riddle. You have a door with a Magic Mouth spell cast on it. Make the door as elaborate or simple as you want, whatever fits your campaign. Could also be a treasure chest, whatever. When the players approach the door, the mouth triggers and delivers a "riddle." The one I used for my campaign was an adaptation of the Sphinx riddle, something like "What walks on its feet in the morning, Swims during the day, but flies at night?" It doesn't matter what the riddle is, the only thing that matters is that it sounds plausibly solvable, and has no answer. The players will drive themselves crazy trying to solve it - my players blew through a two-hour session doing anything they could to find a solution, even after I let them scour the internet for answers.
The trick? The door is unlocked. No traps. No obstacle of any kind preventing them from just pushing the door open and walking through.
EDIT to add: If you want to add an extra layer of frustration, have the mouth repeat the riddle every time they make a guess.
I have forests with no trees, rivers with no water, cities with no people... what am I?
A. A map
There's this really fun riddle from Tales from the Yawning Portal, and it's in the 2014 Monster Manual. I've always liked it. I don't actually know how difficult it might be for your party, but it's worth mentioning here:
Round she is, yet flat as a board
Altar of the lupine lords
Jewel on black velvet, pearl in the sea
Unchanged yet ever changing, eternally
It's the moon
He doesn't have much besides the skin on his bones. Me: I'll take the skin on his bones, then.
"You see a gigantic, monstrous praying mantis burst from out of the ground. It sprays a stream of acid from it's mouth at one soldier, dissolving him instantly, then it turns and chomps another soldier in half with it's- "
"When are we gonna take a snack break?"
This isn't really a riddle that has any actual solution, but I based a one-shot campaign around it and created a solution. The story was that an ancient wizard named Kershawnik had created a library that had been lost ages ago and is rumoured to be priceless. Many had tried to find it throughout the ages. The only clue into finding the library was this gibberish a person was saying over and over again that the party met "at random":
Near a tree by a river there's a hole in the ground,
where an old man of iron goes around and around.
And his mind is a beacon in the veil of the night,
for a strange kind of fashion there's a wrong and right.
This is of course (most of) the chorus of a song called The Riddle by Nik Kershaw with slightly modified lyrics (Aran --> Iron). The solution was that they had to dig a hole near a tree by a river. They found a small ancient iron statue that had a joint in its waist. They had to rotate/wind the torso, so that when they let go it unwound and the head started glowing. They had to place the glowing statue into the hole with any piece of clothing at night, so that the entrance to the library was revealed.
I have a heart no surgeon finds,
A throne that rules a thousand minds.
Within my chest, the winters wait,
And time moves slow behind my gate.
Knights are my fingers, walls my skin,
My moat keeps out, my halls keep in.
I am the war that doesn’t roam—
What am I, more fortress than home?
castle seat of power
Dead on the field lie 10 soldiers in white, felled by three-eyes, black as night. What happened? See if any of you can guess it.
Hiya! You can call me Link. Here’s a bit about me:
Roomba Knight, Architect of the Cataclysm, Foxy Lunar Archpriest. Dubbed The Fluffy Bowman by Golden. He/Him
Theatre Kid, Ravenclaw, bookworm, DM, Lego fanatic, flautist, mythology nerd, pedantic about spelling. I also love foxes, cats, otters, and red pandas!
I love K-pop Demon Hunters and Korean Mythology. If you want to ask me about something, send me a PM!
Èist ri Arirang aig BTS!