Need more random urban encounters? I’ve got a list of 100 DND 5e urban encounters on this page that you can use in your fantasy tabletop RPG campaign. If you like the list, be sure to check out the rest of the site for more D&D content of all types.

Random Urban Encounters

1. Looting. A group of 3d6+5 bandits are looting a shop. They are armed with short swords and short bows. They will fight to the death.
2. A mother and her two children are begging for food or money. The mother is holding a baby in her arms.
3. A couple is arguing loudly about their relationship. Another couple is watching them and laughing at them.
4. A man is selling maps that show the location of a nearby dungeon.
5. Three half-elven bards are singing a song about a local hero.
6. A man is selling an unusual animal. It’s an unusually large rat that can actually talk.
7. A group of 2d6+5 men are arguing about whether or not they should start a war.
8. A couple of men are selling magic items. The items are rare and powerful, but not ethical to use.
9. A woman is selling rare gems. The gems are actually fakes, but she doesn’t know that.
10. A group of 2d6+5 men are arguing about whether or not they should start a war.
11. Three goblins are running through the city, chasing each other. No one is paying attention to them because they’re gnome illusionists having some fun.
12. A wizard is trying to sell a potion that he claims will heal any wound.
13. A priest is preaching about his god’s greatness. He is telling everyone that if they don’t believe in him, then they will burn in hell for all of eternity.
14. A group of men are all wearing the same set of armor. They are trying to get a nearby shopkeeper to buy it from them. They say that it is enchanted. They want 20 gold pieces for it.
15. A man is walking down the street, crying and wailing. He says that he was robbed of everything except his pants. He is asking for help. When people approach, he asks for money. He says he doesn’t even have any pants. He just wants money.
16. A man is walking down the street, singing a song. He is drunk. He is stumbling and slurring his words. He is walking away from the nearest tavern.
17. A group of children are playing a game. They are trying to catch a rat.
18. A group of women are gossiping about someone in the city. They say that she is a witch who lures people into her house and then eats them. They say that she has been seen chasing children into her house.
19. A group of people are talking about the nearby mountains. They say that they were once a temple to an ancient god. They say that they were once full of gold and gems. They say that they were raided long ago, and now there is nothing left but bones and dust.
20. A group of children are playing a game. They are trying to catch a rat.
21. Kitten. A little kitten is sitting on the street. It’s not doing anything.
22. A group of children are playing tag in the street. They’re not in anyone’s way.
23. A drunk man is trying to walk home. He’s not in anyone’s way.
24. A woman is selling flowers on the street. She will sell you one for 1 copper piece.
25. A man is selling paintings of famous people to people as they walk by. He will sell you one for 1 copper piece.
26. A man is selling paintings of famous places to people as they walk by. He will sell you one for 1 copper piece.
27. A man is selling paintings of famous creatures to people as they walk by. He will sell you one for 1 copper piece.
28. A group of men are gathered around a small fire in the street, telling stories about their adventures. They’re not bothering anyone.
29. Two men are arguing about something. They’re not bothering anyone.
30. A woman is selling books about local landmarks and culture. She’s doing rather well for herself.
31. Crier: ‘Great news! The emperor has decreed that all citizens must carry a passport at all times! Anyone without a passport will be arrested!’
32. A street performer is juggling. He is really bad at it. If players give him a copper he will quit and leave in a huff.
33. A street performer looks like he is dancing on a tightrope. He is really just stumbling around. If players give him a copper he will stumble over and demand more money.
34. A priest is leading a group of children around the city. They are all wearing bright red robes. If players approach, he will try to drag the children away.
35. A man is selling apples. He is the best apple seller in the city. Apples cost 1 copper per apple.
36. A man is selling roses. They are very cheap, but they are all wilted.
37. The local thieves’ guild is looking for new members. They are looking for anyone willing to do their bidding, no matter how menial. They have no requirements other than being able to keep their mouth shut. They are also always seeking information about their competition. If players ask about joining, they will invite them to a meeting and offer them a chance to prove themselves by stealing something for them.
38. A man is selling maps. They are accurate maps of the city, but they are very old. They cost 1 copper per map. He sells about one map a week and doesn’t look like he’s ever going to get rich from it.
39. A man is selling rugs on a street corner. They are all very expensive and very nice rugs, but there is a pile of rags on the ground near him, and it’s clear that he’s been making a living by scamming people into buying the rugs when they meant to buy the rags.
40. A man is standing on a street corner, holding up a sign that says ‘Gwouls! Get your gwouls here! Gwouls for sale!’ He looks like he’s been trying this for a while, but nobody’s paying him any attention.
41. Hordes of rats swarm down the streets, devouring food and garbage.
42. A man is standing on a box, preaching to the crowds. They are listening intently and nodding in agreement.
43. A group of children are playing with a ball. They are kicking it back and forth to each other, laughing and having a good time.
44. A group of children are playing with a ball. The ball is enchanted, and when an adult kicks it, it comes back to you like a boomerang. If you throw it in the air, it will return to you after a few minutes. If you throw it into the air and then run away, it will chase after you like a dog!

45. An elderly man is sitting on a park bench, eating lunch. He is reading and seems unbothered by the chaos around him. He seems to be immune to the random enchantments that plague this city.
46. A young woman wearing a flowing cloak is walking down the street, singing to herself. She is totally unaware of the chaos around her, but she is not immune to the random enchantments that plague this city!
47. A group of children are playing with a ball. The ball is enchanted, and when an adult kicks it, it explodes into a cloud of acid!
48. A group of children are playing with a ball. The ball is enchanted, and when an adult kicks it, it explodes into a cloud of fire!
49. A group of children are playing with a ball. The ball is enchanted, and when an adult kicks it, it explodes into a cloud of lightning!
50. A group of children are playing with a ball. The ball is enchanted, and when an adult kicks it, it explodes into a cloud of poison gas!
51. Yawning alderman stumbles into the street, too drunk to stand.
52. A street artist is painting a portrait of the city’s Grand Vizier.
53. A group of children are playing with a ball. One of them will throw it over the wall of a nearby estate, and the others will run after it.
54. A group of young lovers is sitting on a wall, talking quietly.
55. Two elderly men are arguing over which one of them ran faster as boys.
56. A man is selling damaged goods at a discount price. The items are actually quite good, but he is trying to cover up the fact that he has been stealing from merchants. He is hoping that the players will not realize this.
57. A merchant is trying to sell players an item that is actually quite good, but he knows that they will not buy it because it is too expensive. He will try to sell it at full price and then try to sell it again at a lower price.
58. A man is selling maps to a dungeon that does not actually exist.
59. A group of children are running around throwing snowballs at each other.
60. A man is selling expensive maps to a dungeon that does not actually exist.
61. Tired peasants are heading towards the city. They need a place to stay for the night. They are willing to pay for rooms.
62. A group of drunkards are arguing over the price of a barrel of wine.
63. A group of people are selling ‘magical’ potions and scrolls. They are actually selling potions that induce laughter and cause paralysis.
64. A group of people are begging for help. One of their group has been cursed. They want someone to cure the curse. The curse is just a minor annoyance.
65. A man is offering cheap food and water to people. The food and water are bad quality and will likely cause harm to anyone who eats or drinks them. A sign says ‘Fresh food! Cheap prices!’
66. A man is offering maps to a nearby dungeon at a cheap price. The maps are slightly inaccurate and will lead players into a trap.
67. A man is offering magic items for sale at an incredibly cheap price. The items are slightly less powerful than normal items of their type and will break after one use.
68. A man is offering rare magic items for sale at an incredibly high price. The items are actually quite common and can be found outside nearby dungeons at low levels.
69. A group of people are arguing over whether or not the nearby dungeons are dangerous to explore. They are correct but will not admit it to anyone who asks them about it.
70. A group of people are arguing over whether or not they should go into the nearby dungeon. They believe there is treasure inside but will not admit it to anyone who asks them about it.
71. Two large people walk by, carrying a coffin. They are not sure where to bury the body, and they need help – desperately.
72. A group of children are fighting over a ball. A small dog is involved.
73. A man is walking down the street, singing laments about his lost love. He is drunk and appears to be on his way to the nearest bar.
74. A man and a woman are walking down the street, arguing about what to name their new baby.
75. A group of men and women are gathered around a circular board. They are playing a game of chance. The game appears to be rigged – the same man keeps winning.
76. A man and a woman are arguing about what to name their new baby. They are standing in the middle of the street, holding a baby wrapped in blankets.
77. A man and a woman are walking down the street, arguing about what to name their new baby. They stumble and fall, dropping the baby onto the ground. The baby starts crying, but is quickly silenced by its parents.
78. A group of men and women are gathered around a circular board. They are playing a game of chance. The game appears to be rigged – the same man keeps winning.
79. A man is walking down the street, singing laments about his lost love. He is drunk and appears to be on his way to the nearest bar.
80. A man is standing in the middle of the street, yelling at no one in particular about how lazy everyone is in this town.
81. Crier running down the street yelling ‘news of the king’s death has been greatly exaggerated’.
82. A man offers you a free meal at his home. If you accept, he will tell you to sit down and tells you his life story. He will say he was a wizard, and will show you a broom. He will tell you that he was in the tower of the witch and he will show you the broom and tell you about the witch. He will tell you that the witch is still alive, and he will tell you about the broom again. He will tell you that he knows a place where the witch is, and he will tell you about the broom again.
83. A man tells you he is a sorcerer, and he will show you his magic wand.
84. A man needs help finding his wife. He is being followed by a group of men who are demanding she be returned to them. They are threatening to kill him if she is not returned to them soon.
85. The local magistrate is out of town. A group of men are sitting in front of his office arguing about money owed to them.
86. A man in robes bumps into you and says ‘Oh, pardon me’. He will then walk away quickly laughing. If you look down, you will see a pouch full of gold has fallen from his robes.
87. A woman offers to sell you a potion of cure light wounds for 10 gp. If you buy it, it will be vinegar in a bottle labeled as a potion.
88. A man offers to sell you a potion of cure light wounds for 10 gp. If you buy it, it will be a really good potion labeled as vinegar in a bottle.
89. A man attempts to sell you a ring for 10 gp. If you buy it, it will be a ring of polymorph finger that has been cleaned and polished.
90. You see a group of 3d10 high elves walking down the street. If they see you, they will ask if you need any help finding something since they are on their way to see the king.
91. Unexpectedly, a young man approaches the party. The young man is wearing a red cloak and is carrying a wooden staff. The young man will ask the party if they want to join the cult of the Staff of Fire.
92. A group of homeless people are huddled around a fire. One of the homeless people has a large beard. The homeless people are drinking wine.
93. Two men are fighting in the street. One man has a metal breastplate and a sword. The other man has a metal helmet and a metal shield. The men are wrestling.
94. A man is selling vegetables. The vegetables are sitting on top of a large metal shield.
95. A group of children are playing in the street. One child has a wooden sword and is pretending to be a knight. The other children are pretending to be his prisoners.
96. Four men are arguing in the street over a barrel of wine. The men will have bloodshot eyes and will be drunk.
97. Four old women are gossiping in front of their house. One of the old women has a wooden staff. The other three women have wooden staffs.
98. A group of young men are standing in front of their house. One of the young men has a wooden staff. The other young men have wooden maces.
99. A man is selling apples and pears from a cart that’s covered in blood. The apples and pears are bruised and rotten.
100. Two men are fighting over a gold coin that’s covered in blood.

More Random Urban Encounters

If you want even more random urban encounters, head to Random Encounters AI for over 10,000 unique encounters for your tabletop RPG – with more coming all the time. I’ve also got a random dungeon generator that you might enjoy!