Friday Encounter: The Riddling Bridge

I've always been of the opinion that more DMs need to use riddles in their games. Maybe I'm biased - "Riddles in the Dark" is probably my favorite chapter of The Hobbit - but I will maintain that D&D is most fun when it's challenging characters (and players) on all levels, not just how well they can fight (or, more accurately, how good they can roll in combat). Riddles are a very fun way to give some problem-solving opportunities that can't be brute forced, and they don't require a lot of additional mechanics to facilitate, since they can easily be solved through the act of roleplaying. Plus, there's plenty of literary and mythological precedent.

The Riddling Bridge

This encounter can be used in a dungeon or a wilderness environment - anywhere it would make sense for there to be gaping pits or steep cliffs.

The PCs should come across a deep chasm, spanned only by a short but rickety bridge. Opposite the chasm is a creature with the body of a winged lion, and the face of a woman. This is Pherenike, a gynosphinx. She has dwelled by the side of this pass for many years, and she has grown bored - so bored, in fact, that she has taken a liking to toying with travelers. Like all sphinxes, she is quite fond of riddles, and has devised a deadly game.

When she catches sight of the party, Pherenike will welcome them to her abode and present the rules of her game. In order to cross the bridge, one member of the party must answer a riddle for each step they take (it takes about five steps to cross the bridge, so a PC that attempts to cross must answer five riddles to get to the other side of the chasm). For each riddle, they get three guesses. If they cannot correctly guess the answer, or if they at any point admit they don't know, Pherenike will upend the bridge, and they will plummet into the abyss to their doom.

As far as the riddles go, I've included a select few of my favorites, but don't be afraid to substitute your own, or add more if you need to. If you suspect your players might already know the answers, it's a good idea to come up with substitutes. Luckily, you can find riddles pretty easily online. Ideally, you want the players to think, not just remember the answer from hearing it before.

1. I am more powerful than any god and more evil than any demon. The beggar has me, the emperor wants me, and if you eat me, you die. What am I? (Nothing.)
2. He who makes me needs me not. He who needs me uses me not. He who uses me doesn't know it. What am I? (A coffin.)
3. I use fire, water, earth, and air to make a point. What am I? (A swordsmith.)
4. I have a foot but never walk; I have a mouth but never talk. I have a head but never think; I have a bed but never sleep. What am I? (A river.)
5. I lose my head in the morning but get it back at night. What am I? (A pillow.)

Ideally, answering the riddles should be as simple as the players answering them in character. Of course, this does run into the issue of in-character versus out-of-character knowledge. In some cases it's easy to assume that what the player knows, their character would also know. But if Steve has an encyclopedic knowledge of riddles but is playing as Krog the illiterate orc barbarian, you may run into some logistical difficulties. One possible solution is for both the players and the characters to nominate one of their own to answer the riddles, and if the chosen character belongs to someone other than the chosen player, the chosen player temporarily takes control of the character for the encounter - but this won't work for all tables, of course. To prevent cheating, this should be done before any riddles are issued. Another option would be to let PCs make an Intelligence check and get hints if they pass, but again, this takes away from the fact this encounter is meant to challenge roleplaying, not roll-playing.

If a PC fails the challenge, Pherenike grasps her end of the bridge and shakes it, causing the unfortunate challenger to fall off into the abyss. The drop down is 100 feet. If the rest of the party show hostility after this, the sphinx may engage them in combat.

If, however, a PC successfully answers five riddles and crosses the bridge, Pherenike will express shock that anyone could have outwitted her, and throws herself into the chasm instead. On her side of the chasm, the PCs will find her treasure hoard, consisting of 47,000 GP in coins, jewels, and other treasures, plus a Watchful Helm (wearers get a +1 bonus to AC, are aware of their surroundings while asleep, and can cast See Invisibility once per day as a bonus action).