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100 D&D City Encounter Ideas

Downtime in Dungeons and Dragons can be boring. But it doesn’t have to be! Here are 100 Dungeons and Dragons city encounters to make that trip to the next town a little more enjoyable.

You’ll note that few of these lead immediately to “roll initiative.” Instead, these are meant to add intrigue, introduce an important NPC, or perhaps serve as a red herring. And, you know, some will lead to the words “roll initiative,” so that’s nice.


100 Dungeons and Dragons City Encounters

1. A necromancer is using magical means to stuff the ballot box in favor of a particular mayoral candidate in town. The PCs are asked to find the culprit behind the fraudulent votes.

2. A small orphan girl is terrified and shares a wild story about another child at the orphanage who is biting everyone.

3. A severed head rolls down the center street. Attached is a warning sign that reads, “Dis Town Belong Negan.”

4. Farmers just outside of town are panicked because a coven of hags have been burying dead owlbears under piles of cow manure. But why?

5. A child asks the PCs to help him find his pet dog. But this simple task leads them somewhere where they don’t belong.

6. A bounty hunter tracks his target.

7. A noble’s home has delicious apples drooping just over the gate. The house is protected by a magical ward, but what is triggered when a single apple is taken?

8. A monstrous mount lumbers into town. It is ridden by a gnome.

9. Two guards hold a wanted poster. They carefully study the party as they pass by.

10. A smiling merchant roasts rats, frogs, and squirrels on sticks. He offers a bite to the PCs.

11. A chatty bard walks alongside the party. Time for an exposition dump!

12. A group of kobolds found a home in the sewers beneath an alchemist’s shop. The chemicals have done strange things to them…

13. An attractive maiden flirts with you. Her very large husband notices.

14. A naked bard asks for directions to the nearest inn where he left his clothes and money.

15. While haggling in the market the PCs notice people vanish for a few heartbeats then reappear. Nobody finds it strange

16. It is the Annual Wyvern Race. The PCs are recruited as substitute racers for a down-on-their luck faction after a mysterious “accident” disabled the previous team.

17. An evil wizard is hanging from the gallows, the body still smoking.

18. Three mischievous children work on tipping over an occupied outhouse.

19. An overweight town guard, panting heavily, chases someone who nears the PCs.

20. The PCs feel like they are being followed as they stroll through the docks. Who is hunting them?

21. Something goes wrong during a magical performance by a gnome mage. A simple trick summons a beast from another dimension and it attacks the audience and PCs. Is the gnome responsible of is there a more sinister actor pulling the strings?

22. A back alley hides a sinkhole that chutes the party on a slalom slide down into the old pirate’s cove hidden beneath the city.

23. A goblin statue is submerged just off the docks. But why?

24. A bar patron gives the party advice on a quest. All his intel is impeccable, but when they mention his name at the tavern, they’re told he died years ago.

25. A shopping list for potions lies on the street.

26. The local baron has enacted a toll bridge to enter town. Several peasants were unaware, and cannot afford the toll. They beg the PCs for change.

27. The PCs are hired to transport live cargo to the house of a noblewoman. One gets fed after midnight.

28. A PC gets a frantic message from a family member and there is a race around town to find them.

29. An arrow strikes the shop sign just above you, a message wrapped around the shaft.

30. A noble is offended by a PC’s behavior (How dare you!?!) and challenges the PC to a duel at dawn.

31. A loaded wagon travels past the party along Main Street, but it has no apparent means of propulsion.

32. Ruffians attempt to shake the PCs down in an alley. The PCs realize a friend of theirs is among the robbers.

33. There is a mysterious flicker, and one member of your party suddenly stops, paralyzed.

34. An owlbear makes its nest in the horse stables. It’s only trying to protect its eggs.

35. A fireball erupts from a home, blowing up a water barrel, generating a cloud of mist. It appears the PCs are in the middle of a domestic dispute between partners, one a wizard and one a sorcerer.

36. Dozens of oozes are floating in the bay, blocking ship traffic. How did they get there?

37. The PCs must babysit the teenage daughter of the mayor and she’s always looking for trouble.

38. A set of shackles lies outside the city jail.

39. The PCs go looking for a job, but a worn out shop owner presses the deed into their hand and says, “I’m over it. It’s yours!”

40. Two gangs of goblins are seen marching towards the city from opposite directions, one wearing red sashes, the other blue.

41. The local wizard tower is glowing orange.

42. A powerful fighter hires the characters to lock him up for the night. He has contracted lycanthropy and is afraid he will do something he will regret. He is also afraid the pack that infected him might come to find him.

43. A storyteller tells a random story about a creature from an exotic “Monster Guide Book.” The creature suddenly appears from around the corner!

44. Upon returning to your room at the inn, you discover a body on the floor with a dagger just adjacent. You hear guards storming up the stairs.

45. An enormous dragon lands in the street in front of the group. It asks for directions to a certain farmstead just outside of town. It gives the party a generous tip, then flies off saying he intends to raze it to the ground.

46. As the party wanders, a surly fellow approaches: “We don’t like yer kind here!”

47. A tavern owner captured a troll. Patrons are paying 5GP to ‘rastle it.

48. A dozen townsfolk are running after a fleeing woman, attempting to stone her to death for being a prostitute.

49. Two other adventuring groups are arguing just outside the tavern.

50. You see a man-sized shadow just around the block waving its arms at you. “Over here, quickly, I’ve caught one!”

51. A prominent businessman, well-known as honest and good-natured, disappears. The PCs stumble across his body, tattooed with symbols of an evil deity. Was he a cult’s victim or a member?

52. The city’s renowned chocolateer has gone missing! The rewards for his safe return are substantial. If only there was a trail to follow…

53. A plague of rats has befallen the best bakery in town. A fat and greedy wererat can’t resist nightly visits in rat form to gorge himself on the delicious treats.

54. Gnomes are holding a sidewalk sale! They have any number of strange and fascinating contraptions.

55. A little kid falls in front of a charging stagecoach.

56. A cleric accuses the mayor of being a silver dragon.

57. A rare cockatrice egg has gotten mixed into a market shipment and sold to an innkeeper. Anyone who eats it is liable to turn into stone! Trouble is, there are 13 taverns in the city and it is almost time for breakfast…

58. An enemy named Bauer has placed magical bombs throughout the city. The PCs need to find them and eliminate them within 24 hours.

59. Ladies clothing and under clothing are strewn just outside the doors of the PCs room at the inn. How did these get here?

60. A young woman approaches the PCs, insisting one of the party is her husband who went missing two years ago. The other townsfolk agree, despite the PC not knowing her.

61. Some hapless citizen is harassed by a ruffian named Biff. Will the characters step in to save him?

62. The characters recognize the mayor’s son climbing out of a disreputable two-story building.

63. Reports come in about a ghost haunting a dark alley in a city, and anyone investigating the ghost ends up dead. The story is an elaborate hoax created to keep people away while crooks are attempting to break into a vault of a nearby building.

64. A famous adventurer was hurriedly approaching the PCs, yet he dropped dead mid-stride. Why was he coming toward your table?

65. A circus is set up just outside of town. A barker cajoles you to “come inside and see what wonders it holds.”

66. A group of young, rude nobles are racing horses through the streets and nearly ride down the characters. How the party handles this situation will determine how well they are received by the various factions in that city.

67. A PC sees a beautiful woman sunbathing on a nearby rooftop. He’s spotted and waved over.

68. Rumor has it there is an underground fight club in the warehouse district. They’ve been tasked with finding it and shutting it down. But will they want to join instead?

69. The tavern owner’s daughter is missing and he’s offered you all the whiskey you can drink if you can bring her home safely. Turns out, she’s the ringleader of a gang.

70. Townsfolk have been reporting sightings of strange creatures around town. But when questioned about it the next day, it’s like they didn’t see anything.

71. It’s impossible to start a fire within the city walls. The most powerful mages, flame eidolons, and candlemakers have tried until they’re blue in the face; it just won’t catch. A clan of frost trolls has taken up residence nearby, but it can’t be THAT simple, can it?

72. You arrive in town to find that hobgoblins have taken over. They’ve crudely replaced the mayor and subjugated the townspeople, but they also control the soldiers under threat of destroying families.

73. A new healer has come to town, the most grievous wounds are healed good as new. Unfortunately, he’s a charlatan clouding the victims mind so they only think they’re back to full health. The wounds still exist and it’s only a matter of time until they flare up again…

74. The great oak in the town square has blossomed leaves of tremendous color. Magenta, azure, and puce adorn its branches. Which would be great, except birds refuse to roost among the leaves, and it’s giving off a foul odor.

75. A young boy has gone missing from his home. Everyone assumes him dead, except his mother swears she can still hear him. Turns out, there’s a tunnel system under the city where a creature is holding him hostage.

76. Once a year a colorfully clothed benefactor sneaks into town under cover of night and leaves trinkets for the children of the town. The town must provide an annual offering to keep the benefactor from collecting a decidedly darker form of payment.

77. A traveling minstrel challenges the wisest looking member of the party to a storytelling contest.

78. Midsummer’s Eve has arrived, and flowered crowns are all the rage. The Fae always come to help celebrate, but the celebration comes and goes without any sign of them. Three days later, a battered brownie covered in frost stumbles through the gates and mutters something about Eternal Winter before collapsing. Snow begins to fall.

79. A new song is gaining popularity in the taverns and music halls of the city, far from being a listening experience only, listeners also experience hallucinations. Every time they hear the song the visions get more vivid until they become so real the listener is whisked to a different plane entirely.

80. A legendary paladin renowned for victory in battle and training many acolytes has gone missing, seemingly having turned their back on the order. Can they be found again in a time of need?

81. A great northern city is experiencing rising temperatures. Creatures outside of town are shedding every bit of their white fur due to the unprecedented temperatures, their pitch-black skin beneath becoming exposed, causing them to appear unnatural, as if they’re living shadows. Meanwhile, they grow lean and bony, ever more wraith-like. Now, the shadow creatures are moving toward town, setting their ebony gaze on the thing they blame for this calamity—us.

82. A tavern patron tells the PCs to repent of their sins. He knows details.

83. A man calling himself “The Shoveler” has moved into town, assuming the position of chief caretaker of the local cemetery. But judging by what he’s digging up, does he shovel too well?

84. A local hero named Gjallerabru is famed for standing alone against an invading horde. But it appears that he somehow cheated death, because death’s emissary has come a lookin’.

85. When a wagon carrying a gigantic cage rolls up into town, the people are struck with curiosity. But when the tarpaulin is removed, there is only a strikingly cute turtle. “Thing’s vicious. Don’t let those enticing eyes fool ya. And don’t look at it too long.”

86. The candles in town WON’T GO OUT. Every bit of flame becomes perpetual and any fires need to be completely quenched or else they will reignite. This is leading to problems, not just for infrastructure, but for the Mage’s College, where experiments are more delicate.

87. The town tax collector has been kidnapped. Curiously enough, all of his gold was left behind; whoever took him wanted the man, not the money…

88. When the armor and weapons at the blacksmith’s forge suddenly become animated, the surrounding area evacuates. A particularly large suit of armor shouts, “I shall defend my birthplace!”

89. Shiny objects have been disappearing all over town. There seem to be an awful lot of crows hanging around lately, but it couldn’t possibly be them. Could it?

90. When the three capstones begin to glow brightly, the Order of the Scarab becomes nervous. The stones haven’t lit up in centuries, and they had assumed the danger had passed…

91. One of the town wells allegedly has curative properties. It has caused the gradual expansion of the walls to the point where some citizens have taken to living down there.

92. The town gallows hasn’t been used in decades, but one morning a swollen noose is found swinging from the beam. When the rope-maker is found to be missing, the plot only thickens…

93. The group arrives late at night at a tiny village. They secure accommodation and food from the friendly locals and fall asleep. In the morning the village is empty and ruined, as if abandoned years ago.

94. Under the bridge downtown, a body has been found. Exotic spices and peppers surround the crime scene.

95. When a strange island floats into view, the town is torn about investigating it. The sailors are eager to explore the new land, but the shaman warns against rushing in too hastily.

96. There’s a new face in town. Or at least…a new figure. You haven’t been able to see their face. In fact, nobody has. Their lavender cloak is pulled tight to conceal their features while they whisper, “The Firestorm is nigh.”

97. A little girl is watching you from the alley. The next time you glance over, you see a wolf run away.

98. The local innkeeper has baked the MOST DELICIOUS strawberry rhubarb pie. Nobody can stop eating once they start.

99. A note slides under the door of your room. On it are the words, “Good luck tomorrow. You’re going to need it.”

100. An ecstatic shop owner presses a cigar into your hands and proclaims, “It’s a girl!”


And if you’re looking for even more encounters, check out this list of 100 Roadside Encounters we whipped up to spice up your travel!