When traveling between towns, forts, and dungeons by steam vehicle, the party has a 10% chance to encounter a joke or gag quest. I then make the party roll from a table of unsolved encounters. And the encounter my party pulled during Session 11 was the Toughest Riddle Ever encounter.
Encounter: Toughest Riddle Ever (From the module available here)
The party encounters a life-size ceramic statue of a human male bard, head thrown back, cackling. They must stop for this statue because when their vehicle (steam-powered) comes within 50 feet of the roadside statue, their engine cuts out, and no amount of Mechanic, Blacksmithing, or Engineering skill can start it again. (See; Craft Skill – Pathfinder)
There is also a small hollowed-out rusted ruin of a Gnomecycle sitting next to the statue. On the pedestal of the statue is the following riddle:
What has flown, but never moved
What knows all riches, yet is poorer than peasants
What feels all hurts, yet never scowls
What laughs, but weeps eternal
No matter what the party guesses, the statue never moves and their engine won’t start. There is no valid answer to the riddle. The only way to start the vehicle again is if the statue is smashed. In the middle of the ruined ceramic statue is a random magical item.
(DM’s note: The difficulty of this encounter is entirely dependent on the disposition of the party. If you’re traveling with a group of impulsive, cartwheeling douchegoblins, this statue will go down faster than a bowling pin.)