D100 City Random Encounter Table 5e DND

I’ve put together a list of 100 random city encounters for your fantasy tabletop RPG campaign! Feel free to use. If you like the idea-seeds (as I call them), keep reading to the end to find even more tabletop goodness. Thanks for reading!

D100 Random City Encounters

1. Mournful music can be heard from the graveyard. The players can see a group of humans and elves digging a grave and placing a coffin in it. They will ignore the players.
2. A man dressed in black is standing on a corner, muttering to himself. If the players approach him, he will ask for help finding his lost love. If the players help him, he will try to stab them in the back.
3. A group of drunk men are singing a song about the local lord and how great he is. They will stop when they notice the players.
4. A group of children are playing a game of hide-and-seek in an alley. If players join in, they will notice that one child is missing and is hiding in a barrel nearby.
5. A man is sitting on a bench, frowning. He will tell players that he was mugged last night and robbed of everything he had. Players can give him some money to help him out. The man is an NPC spy for the local thieves guild and will try to steal players’ possessions while they sleep later on in the evening.
6. A group of children are playing with a ball and get into a fight. A woman comes out of her house and yells at them to stop fighting or she will beat them all up. She is holding a wooden spoon and looks like she means business!
7. A lone woman wearing a dark cloak and carrying a staff can be seen walking down the street. She appears to be looking for something or someone. If the players approach her, she will ask them if they have seen ‘him’. She won’t say who ‘him’ is but will offer a reward if they help her find him.
8. The players can hear an argument coming from a house nearby. If they investigate, they will find two men arguing over some money that was owed to one of them. They will stop arguing if they notice the players and offer them some ale if they stay and listen to their story. They will continue their argument once the players get drunk enough!
9. A drunken nobleman staggers down the street, singing loudly about how much he loves his wife! He will stop and offer players some ale if they buy him one!
10. A group of children are playing with a ball and get into a fight. A man comes out of his house and shoos them away before heading back inside.
11. Barmaid and drunk. The drunk is trying to convince the barmaid to sleep with him.
12. A group of children are playing hide-and-seek.
13. A group of men are arguing about whether or not a horse is a mammal.
14. A group of women are gossiping about the city’s latest scandal.
15. A drunk man is trying to steal a horse from a stable.
16. A woman is trying to sell a basket of apples.
17. A woman is trying to sell a basket of flowers.
18. Two men are arguing about whether or not the sun orbits around the Earth or the Earth orbits around the sun.
19. Two men are arguing about whether or not the moon landing was real or if it was staged in a film studio.
20. Two women are gossiping about the city’s latest scandal.
21. Ternoy, the Demon Prince of Gnolls, has summoned 2d6+2 gnolls to attack the PCs. These gnolls have been transformed by Ternoy’s magic power and now look more like demon-wolves than gnolls. If the PCs kill the gnolls, Ternoy will send 2d6+2 more.
22. A group of elderly women is protesting outside of a bank. They want the bank to give them their money because they think that the bank has been stealing from them over the years.
23. The PCs see a man who looks like he is about to commit suicide by jumping off a bridge into a river below. The man says that he is tired of living and wants to die. He asks the PCs to join him in jumping off the bridge into the river below.

24. The PCs see a man who looks like he is about to be robbed by a group of well-dressed men. The well-dressed men are demanding money from the man who looks like he is about to be robbed.
25. A group of men are holding up a group of women and demanding that they give them all of their money and valuables. The women are crying and begging as the men hold them at gun point.
26. A group of young children are playing in the street. The children are playing a game where they pretend to be adult heroes who are fighting against an evil king and his army of orcs, goblins, and dragons.
27. A group of men are arguing about whether or not they should hire a group of mercenaries to go with them on an adventure that they are planning on going on. Some of the men want to hire the mercenaries because they are scared, but others don’t want to hire them because they think that it’s going to cost too much money and that they can handle things themselves without needing any help from any mercenaries.
28. A man is standing on top of a tall building near the center of the city, threatening to jump off of the building if anyone comes near him or tries to talk to him or reason with him or anything like that. This is not a suicide attempt, but instead this is a protest against the government for not doing anything about all of the crime in the city and for not providing enough protection for its citizens.
29. A group of children are playing a game where they pretend that they are adventurers who are fighting against a dragon in an underground dungeon filled with treasure and magic items and traps and monsters and all of that good stuff.
30. A group of adults are arguing about whether or not they should hire a group of mercenaries to go with them on an adventure that they are planning on going on. Some of the adults want to hire the mercenaries because they are scared, but others don’t want to hire them.
31. Unexpectedly, you see a local priest being chased by a giant snake. The snake is not attacking, it is just trying to catch the priest. The priest is running as fast as he can. If you help the priest, he will tell you that he is in trouble because he owes some bad guys money. He will offer to repay you with some magic items if he can just get away from the snake.
32. A group of local kids are playing with a ball. The ball accidentally bounces into a nearby building, breaking a window. The kids will run away. The players can either deal with the owner of the building or try to fix the broken window themselves.
33. A group of men are talking about how terrible their jobs are. One of the men is a blacksmith. If players talk to him, he will tell them about how much he hates his job and how he wants to quit but he has no other skills and no other way to make a living.
34. You see a group of people gathered around a stage. There is an old man on the stage who is telling stories about his adventures as a younger man. The stories are very long and very detailed. If players listen long enough, they will gain minor knowledge about an interesting dungeon nearby.
35. Two men are arguing about whether or not a nearby dungeon is haunted. One man says that it is haunted, the other says that it isn’t haunted at all. If players talk to them, they will reveal that they are both right and wrong at the same time.
36. You see a man who appears to be drunk stumble around town. He passes out at random places, waking up and stumbling around again after a few minutes. He is actually a spy for an enemy nation. His mission is to get information on the town’s defenses and then get back to his Lord as quickly as possible.
37. A group of people are gathered around an elderly woman who is telling stories about her adventures as a younger woman. The stories are very long and very detailed. If players listen long enough, they will learn about an interesting dungeon nearby.
38. A group of men are gathered around an elderly man who is telling stories about his adventures as a younger man. The stories are very long and very detailed. If players listen long enough, they will learn about an interesting dungeon nearby.
39. A group of young men are gathered around an elderly man who is telling stories about his adventures as a younger man. The stories are very long and very detailed. If players listen long enough, they will learn about an interesting dungeon nearby.
40. You see a man who appears to be drunk stumble around town. He passes out at random places, waking up and stumbling around again after a few minutes. He is actually a spy for an enemy nation.
41. Pestilence has struck this district. A random resident in the area will become ill and cough blood for several days. If the players do not help, the illness will spread to everyone in the area. The illness is caused by a necromancer in a nearby tower.
42. A group of revelers are celebrating their recent marriage. The party is about to head back to their home, but first, they want to stop at the first tavern they see for one last drink.
43. A group of noblemen are taking a stroll through the city. They will run into the players and invite them to their party that night. If the players accept, they will be treated like kings and queens for the night. If they decline, they will be scowled at and told to go away.
44. A group of thieves is planning a heist in this district. They are currently scouting out the area and looking for potential threats and traps around the area they plan on robbing.
45. A man is running down the street yelling about an evil cult that is setting up in the area. He says he has evidence that they are up to no good, but he needs help getting it out of his house before they find it and kill him.
46. A group of revelers are celebrating their recent marriage. They are so drunk, they will fall down and pass out on the street if the players don’t help them back to their home safely.
47. A man is selling maps to an underground dungeon that no one knows about except him. He’s selling them for an extremely high price because he doesn’t want anyone else to discover his secret dungeon before he does something bad there.
48. A group of soldiers is standing guard outside a building on the corner of a street in the city. The soldiers are protecting something inside that no one else knows about yet.
49. A group of revelers are celebrating their recent marriage. They are so drunk, they will fall down and pass out on the street if the players don’t help them back to their home safely.
50. A group of nobles are taking a stroll through the city. They will run into the players and invite them to their party that night. If the players accept, they will be treated like kings and queens for the night. If they decline, they will be scowled at and told to go away.
51. Wagon full of grain is overturned and blocking the road.
52. The road is blocked by a wagon full of hay.
53. A man is standing on the side of the road, weeping. If anyone stops to ask what is wrong, he will tell them that he has lost his donkey.
54. A group of children are playing in the street.
55. A group of men are standing around on the side of the road, talking about their wives.
56. A man is standing on the side of the road, talking to a large dog that is standing on its hind legs.
57. A man is sitting on the side of the road, weeping. If anyone approaches, he will tell them that he has lost his donkey.
58. A man is sitting on the side of the road, telling everyone who passes by that he has lost his donkey.
59. A group of children are playing in the street. One of them is pretending to be an ogre and is threatening to eat anyone who passes by.
60. A wagon full of grain has overturned but it is not blocking the road.

61. FOUR BANDITS are robbing a carriage. The bandits are a bandit captain, a bandit lieutenant, a bandit sergeant and a bandit warrior. The bandits demand that the players pay them 10 gold coins or they will be killed.
62. A group of 2d6+3 GONZO SAVAGES are attacking a group of 2d6 city guards. The savages are a savage chief, a savage champion, a savage lieutenant, a savage warlord and 2d6+2 savage warriors. If the players help the city guards, the city guards will help them later on. If the players help the savages, the savages will help them later on.
63. A group of 2d6+3 ARMORED KNIGHTS are riding through town on their way to battle an army of Orcs and Goblins. The knights are a knight captain, a knight sergeant and 2d6+2 knights.
64. A group of 1d10+1 MERCHANTS are selling goods in front of their shop. The merchants are a merchant captain, a merchant sergeant and 1d10+1 merchants.
65. A group of 2d10+2 TRADERS are selling goods in front of their shop. The traders are a trader captain, a trader lieutenant and 2d10+2 traders.
66. A group of 2d10 MERCHANTS are selling goods in front of their shop. The merchants are a merchant captain, a merchant lieutenant and 2d10 merchants.
67. A group of 1d4+2 THIEVES are burgling a house. The thieves are a thief captain, a thief lieutenant, a thief sergeant and 1d4+2 thieves.
68. A group of 2d6 MAGES are studying in an abandoned building. The mages are a mage captain, a mage lieutenant and 2d6 mages.
69. A group of 3d4 MERCHANTS are arguing about prices in front of their shop. The merchants are a merchant captain, a merchant lieutenant and 3d4 merchants.
70. A group of 1d4+2 MERCHANTS are arguing about prices in front of their shop. The merchants are a merchant captain, a merchant sergeant and 1d4+2 merchants.
71. ZOMBIE ATTACK! A group of 4d4 zombies attack a small group of players. They will attack the players first. If the zombies are defeated, the players will find 1d8 gold pieces on their bodies.
72. A group of 3d10 men and women dressed in robes approach the players. They say they are members of a local wizard’s guild. They want to know if the players are members of the wizard’s guild. If the players say yes, the men and women will ask for a donation to help with a local event. If the players say no, the men and women will walk away with a smirk on their faces.
73. A man approaches the players and offers to sell them a magic potion that will cure any poison. The potion is actually water with a drop of red food coloring in it.
74. A group of 2d6 guards approach the players and ask them to accompany them to a local graveyard. The guards want to make sure no one steals any bodies from the graveyard. The guards will attack anyone who doesn’t comply with their demands.
75. A salesman approaches the players and offers them a deal they can’t refuse. He offers to sell them a bag of 1d10+2 random gems for 1d4+2 gold pieces each. The gems are actually random rocks with polished sides.
76. A group of 1d4 guards approach the players and ask them if they have seen any suspicious people in the area recently. The guards want to know if any strangers have been in town recently. The guards will attack anyone who looks suspicious to them, even if they haven’t been in town long enough to be considered a stranger.
77. A local merchant approaches the players and asks them if they have seen any suspicious people in town recently. He has lost several items from his store and he thinks someone is stealing from him, but he doesn’t know who it is or how they are doing it.
78. A group of 2d6 men and women dressed in robes approach the players and ask them if they have seen any suspicious people in town recently. They want to know if any strangers have been in town recently. They are actually part of a cult that is trying to find out what people know about them so they can keep it secret.
79. A group of 2d6 children approach the players and ask them to help them catch some rats in their home. The children are actually cultists who want to capture some players to sacrifice them to their god later on.
80. A group of 1d4+2 men and women dressed in robes approach the players and ask them to help them catch some rats in their home.
81. Eerie lights can be seen at night in the graveyard. If a PC investigates, they will find that the Cult of Zan has been resurrected. They will have to deal with six Zan cultists.
82. A group of 1d4+1 thieves are trying to rob the local temple. If the players do not stop them, the thieves will steal and try to sell holy relics. The thieves will attempt to escape before more guards arrive.
83. A group of 1d4+2 guards are on patrol. They will stop and question any PCs acting suspiciously.
84. A man is wandering the streets, babbling about how he is looking for his lost pet cat. If the players ask, he will tell them that he found a magical cat in the forest and it has been acting weird since then. He will offer them a reward if they help him find his pet. If players accept, he will lead them to the Cult of Zan.
85. A group of 2d6 merchants are transporting their goods in a large wagon. They will ask any PCs they see if they want to buy anything from their wagon. They have 2d6 random items for sale. If the players buy something, they will be ambushed by 2d6 thieves who will steal everything they have.
86. A group of 2d6 thieves are robbing a merchant’s cart. The merchant will run up to any PC and beg them to help him. The merchant will give the players 2d6 random items for free if they help him stop the thieves from robbing him further.
87. A group of 1d4+1 guards are on patrol. They are looking for a man named James Grogan, who has been accused of thievery. They will arrest any male PCs with his description, regardless of their actions.
88. A man is wandering the streets, babbling about how he is looking for his lost pet rat. If the players ask, he will tell them that he found a magical rat in the sewers and it has been acting weird since then. He will offer them a reward if they help him find his pet. If players accept, he will lead them to a Cult of Zan shrine in the sewers.
89. A group of 2d6 cultists are praying at a shrine to Zan in a dark alleyway. If players approach or are noticed, they will attack them.
90. A group of 2d6 merchants are transporting their goods in a large wagon. Their wagon is covered with a canvas tarp, but if anyone looks under it, they can see that they are transporting several barrels of ale and wine under it.
91. Gossipers are talking about how a woman was killed by the cult of Andros. They say she was a member of the cult.
92. A man passes by, wearing a cloak and a mask. He looks like he’s up to something. He’s not.
93. A group of people are arguing about the end of the world. They are saying that it’s coming soon.
94. A man is standing in the street, singing a song about the lord of the city.
95. A woman is standing in the street, yelling at her husband. She says he’s been cheating on her. She threatens to leave him.
96. A group of people are talking about a man named Sigfried. They say he’s a member of the cult of Andros.
97. A group of people are talking about a crazy man named Sigfried. They say he is a member of the Cult of Andros and he’s trying to start a war between the churches of the city and the cult of Andros.
98. A group of people are talking about how a man named Sigfried was recently arrested. They say he was a member of the cult of Andros and he was trying to start a war between the churches of the city and the cult of Andros.
99. A man named Sigfried is talking about how he’s a member of the cult of Andros and he’s trying to start a war between the churches of the city and the cult of Andros.
100. Two young children are playing with a toy castle. They’re trying to get their toy knights to battle it out with each other.

More Random City Encounters

If you want even more random city encounters, be sure to check out Random Encounters AI where you get over 10,000 more free encounters. I also run LitRPG Adventures, a set of over 2 dozen RPG tools powered by GPT-3 from OpenAI. We’ve also got a library of over 25,000 already generated items for you to use in your tabletop game. Check us out today!