D&D 5e Random City Encounters: Best D100

Need some D&D random city encounters? I’ve got a list of 100 here, or you can head over to Random Encounters AI for even more. I’ve been using GPT-3 from OpenAI to generate all sorts of RPG content for fantasy tabletop campaigns. Enjoy this list of random city encounters for Dungeons & Dragons, Pathfinder, or other tabletop RPG systems.

Random City Encounters for D&D 5e, Pathfinder, and more!

1. A man is selling maps of the city.
2. A group of men are talking about a new play at the local theater. They don’t want to go because it’s too expensive. They are trying to decide how much they are willing to pay.
3. A group of men are talking about a new tavern in the city. They’re not fans.
4. A man is selling maps of the sewers beneath the city. He says they are accurate, but he has been drinking so it’s hard to tell.
5. A man is selling jewelry made out of silver and gold. He says it’s real silver and gold, but it’s probably not. He says he can get the players a good deal if they buy now.
6. A group of men are talking about the weather and how it’s getting colder every day.
7. A group of halfling women are talking about the weather and how it’s getting warmer every day.
8. A man is selling maps of the city’s catacombs, which supposedly lead to a cave filled with gold and jewels and even treasure from other dimensions. He says he has been there himself.
9. A man is selling maps of the sewers beneath the city. He says they are accurate, but he is drunk and cannot be trusted.
10. Two men are arguing over whether or not a third man is telling the truth. The third man says he has been to the cave full of gold, but the other two aren’t sure if he’s lying or not.
11. A man has set up a stand selling candles. They’re very cheap, but he says they’re made from a special recipe that will keep the candle from ever burning down, even if it’s left in a hallway.
12. A wizard named Dr. Robert has set up a small booth in an alley. He is selling small glass vials of an elixir he created to cure any disease. He says that one vial will cure any disease, even the worst of them.
13. A man is selling small charms he says will repel rats. They look like they’re made of copper and have a rat shape on them.
14. A woman has set up a stall to sell small statues of kittens. They’re very cute.
15. A man has set up a stall to sell books. The books are titled ‘Secrets of the Unknown: A Collection of Facts About Things Normal People Don’t Know About.’
16. A man is selling scrolls. He says they are copies of what he claims is an ancient text, but they seem to contain nothing but gibberish.
17. A woman is selling small bottles of a liquid that she says will increase a person’s strength if they drink it before performing any physical task.
18. A group of men are gathered around an old woman who is telling stories about local monsters that were fighting each other long before the city was built. She says that one day one of those monsters will return, and the others will return with it to fight again. People should be prepared for this day, she says, because the monsters are much darker and more powerful than the ones anyone has seen before. It’s a little hard to tell if she’s pulling people’s legs or not because her stories are so crazy, but there are other people listening to her stories as well and they don’t seem to be laughing.
19. A woman is selling books that she says contain information about people who have come back from the dead and then returned home. They seem to be about different people and different cities, written by different people at different times. They have different titles like ‘Stories of the Dead’ or ‘The Dead Are Alive’ or ‘Dead Again!’ or ‘Back from the Grave.’
20. A man is selling maps that show a way through the mountains to an oasis that no one has ever been able to find before, but he says if people follow his map perfectly then they’ll find the oasis with ease.
21. The party sees a man being beaten by a group of thugs. If they help him, the thugs will turn on them.
22. A man is standing on a street corner, shouting at passers-by. He is wearing a robe, but it is very dirty and ragged. If the players talk to him, he will ask for money. If they give it to him, he will smile, thank them, then run away laughing.
23. A man is standing on a street corner, shouting at passers-by. He is wearing a robe, but it is very clean. If the players talk to him, he will ask for food. If they give it to him, he will smile, thank them, then walk away.
24. A group of performers are performing a play about a group of adventurers who are going on a quest to find treasure. The actors look and dress like the party. The play is funny.
25. A group of street performers are performing a play about the local lord. They are making him look like a fool. They are about to get arrested when the party intervenes on their behalf. The play is funny.
26. A man is standing on a street corner, shouting at passers-by. He is wearing a robe, but it is very clean. If the players talk to him, he will ask for food. If they give it to him, he will smile, thank them, then walk away.
27. The party sees a group of people outside a house chanting, ‘Death to the tyrant!’ They are about to storm the house!
28. A group of children are playing ‘Bandits and Raiders’. They are pretending to be raiders who are trying to steal from the local lord’s treasury. The children are ready to do anything to get into the treasury.
29. A group of men are standing outside a house chanting, ‘Freedom!’ They are about to storm the house.
30. A group of men are standing in front of a house chanting, ‘Justice!’ They are about to storm the house. If the party intervenes, they will get in trouble with the local authorities. The party might go to jail themselves for disturbing the peace.
31. A thief is trying to sell some goods at a market, but they’re stolen. If players try to point this out, the thief will attack them.
32. A man is trying to sell a rare map. The map is of a dangerous area, but it’s worth it. If the players try to buy the map, a rival group of thieves attack them.
33. A group of men are standing outside a tavern, talking about an old legend. The legend is about a dragon that is sleeping underground in a nearby town.
34. A group of men are standing near a temple, talking about an old town legend. The legend is about a dragon that is sleeping just outside the town’s walls.
35. A group of men are standing next to a fountain, talking about an old, twisted legend. It is about a dragon that is sleeping in the middle of the town’s main plaza.
36. A group of men are standing in the street, talking about an old legend. The legend is about a dragon that has been seen flying over the town at night.
37. A group of men are standing in an alley, talking about an old legend. The legend is about a dragon that has been seen sleeping under a local tavern.
38. A man is trying to sell a rare potion. The potion is supposed to give the drinker magic abilities, but it actually just causes them to pass out for an hour, then they wake up with a hangover.
39. Two men are arguing about whether or not there’s a dragon living in a nearby cave system.
40. A group of men are arguing about whether or not there’s a dragon sleeping in the city’s main plaza.
41. A man and woman dressed in fine clothing approach the party, asking if they have seen their daughter. Their names are Appan and Ehelda, and their daughter’s name is Alyana. They will reward the party for returning her safely to them.
42. A group of 2d6 mercenaries are looking for work. They have been traveling for a long time, and they are looking for a place to stay for a while, until they find work again. They will work for the party for a while, as long as they are paid.
43. Two priests of a sect of wizards are fighting over the sect’s beliefs. One believes that magic should only be used for good, while the other believes that magic should only be used for evil.
44. A group of 2d6 soldiers are on their way to the castle. They are looking for work, and they will stay as long as they find it.
45. A group of 2d6 soldiers are on their way back from a battle. They were hired by some nobles to fight off some goblins or orcs or something like that. They will talk about their experience, but if pressed, they will admit that it was not as glorious as they first thought it would be.
46. A man named Marlon is trying to sell some old weapons and armor he has collected from abandoned castles and keeps and what not. He has quite a lot and is willing to sell it cheap.
47. A woman is selling shoes. She has some really nice shoes, but the party can tell that they are not very good quality. If the party asks, she will tell them that she is an elf and she is looking for her lost kin. She will tell them that she is willing to give them some good information if they buy a pair of shoes from her. She will tell them that the elves live in a place called the Black Forest. It’s not too far from here.
48. Two men are having a friendly game of dice. They will invite the players to join in with them and play a game or two.
49. A group of 2d6 merchants are selling their goods in the street. They have some good deals on some things, but the party can tell that they are cheap knockoffs of what they appear to be.
50. A man named Gerald is selling some maps he has drawn himself. He has drawn up some maps that show the locations of hidden treasure, dungeons and keeps, etc. He can’t draw very well, but he can sell them cheap if the party gets him some good wine or ale.

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51. A group of art merchants are setting up their displays. They’re talking about the money they hope to make from the players when they arrive.
52. An elderly man is offering to sell the players a map of the city. He wants 40 silver pieces for it. It is a map of a nearby tomb. The tomb is occupied by a ghoul.
53. A man is looking for a lost dog. He is offering a reward of 5 copper pieces to anyone who can find it. The dog is really a small mimic.
54. A man who was mugged is now convinced he was attacked by a vampire. He is looking for someone to destroy the vampire’s remains. The man’s name is Mr. Channing. The vampire’s remains are actually the remains of his dog.
55. A group of men are looking for a lost ring. They’re offering a reward of 10 gold pieces to anyone who can help them find it. The ring was stolen by an ape.
56. A group of men are looking for a lost cat. They’re offering a reward of 10 silver pieces to anyone who can help them find it. The cat was stolen by a monkey.
57. A group of children are looking for a lost dog. They’re offering a reward of 5 copper pieces to anyone who can find it. The dog is really a small dragon.
58. A group of men are looking for a lost child. They’re offering a reward of 10 gold pieces to anyone who can find her and lead her safely home again. The child’s name is Sally. The child is really a small demon pretending to be a young human girl.
59. A group of children are throwing rocks at a statue of a cat. The children are being watched and harassed by a group of adults. The adults want to punish the children and are willing to fight to do so.
60. A drunk man is stumbling down the street and singing about a treasure he’s looking for.
61. A priest of Olidammara approaches the party, to invite them to a party at the local thieves’ guild. There will be music, dancing, food and drink. The party can expect to meet a number of famous rogues and outlaws there.
62. A man is selling boxes of candied fruit, which look suspiciously like rat skulls.
63. A large group of children are throwing rocks at a statue. They will run away if they are approached.
64. A local merchant is trying to sell a suit of +1 plate armor. It is actually made of paper, but it looks convincing if the buyer isn’t paying attention.
65. A local merchant has a wagon full of barrels. He is trying to sell them as fast as he can before they start leaking and ruining his stock.
66. A local merchant has a wagon full of fake 1 gp coins. He is hoping to sell them as fast as he can before people realize they aren’t real.
67. A local merchant has a wagon full of bags of beans. When people try to steal them, he shouts ‘Thieves!’ and points at them. His plan is to sell them as fast as he can before someone realizes they aren’t real.
68. A group of children are playing a game where they tie a string around their fingers and try to lure each other into traps. If players get involved in the game, they learn that the children are playing a game called ‘Tie a string around your fingers and see how long you can go without getting caught in a trap.’
69. A group of children are playing a game where they throw rocks at each other’s heads. If players try to stop them, they will yell ‘It’s just a game! Quit ruining our fun!’
70. A group of children are singing a song about a local thieves’ guild that is not meant to be a flattering portrayal of the guild’s leaders.
71. A man is standing on a corner, yelling at passersby to beware of the goblins and monsters in the city’s sewers. He will warn them one last time before attacking. He is actually the first stage of a multi-stage quest.
72. A group of people are arguing on the street. They are all merchants, trying to get people to buy their goods from them by price-fixing.
73. A group of men and women are holding up a large mirror, trying to catch a glimpse of their own reflections. If players approach, they will say that they are trying to get a good look at their reflection. If the players look in the mirror, they will see the reflection of a monster in the mirror.
74. A group of people are holding up a mirror in order to catch a glimpse of a reflection of a beautiful woman.
75. A group of people are holding up an old mirror in order to catch a glimpse of the past.
76. A woman is standing on a corner, yelling at passersby to beware of the vampires in the city’s sewers. She will warn them one last time before attacking. She is actually the first stage of a multi-stage quest.
77. A man is standing on a corner, yelling at passersby to beware of the ogres in the city’s sewers. He will warn them one last time before attacking. He is actually the first stage of a multi-stage quest.
78. A group of people are arguing about the location of a treasure in a nearby dungeon.
79. A group of people are arguing about the location of a treasure in a nearby dungeon. They are actually talking about a different dungeon that has nothing to do with this one.
80. A group of people are holding up a mirror, trying to catch a glimpse of something behind them
81. A man offers to sell you a very rare and expensive sword. The sword is cursed and will cause 1d4+1d4+1 points of damage to the wielder each day, unless the wielder makes a Will save each day when they wake up. The seller will not tell the buyer about the curse until after they have bought the sword. The seller is an elderly halfling who has no idea what he’s selling.
82. A group of halflings are running through the street, pursued by a group of orcs. The halflings are laughing and having fun, while the orcs are yelling angrily and waving their swords.
83. A human wearing a dark cloak stands on a street corner, glaring at passersby with a look of hatred on his face.
84. You see a group of men standing around a large cage, which contains a pair of large, angry wolves. The men are telling people not to touch the cage, or the wolves will eat them. The men are actually slave traders, who are selling the wolves as dinner to rich people in the city.
85. You see a group of armed men standing around a large cage, which contains a pair of angry lions. The men are telling people not to touch the cage, or the lions will eat them. The men are actually slave traders, who are selling the lions as bodyguards to rich people in the city.
86. A group of men are standing on a street corner, yelling at passersby that they are in danger and should follow them to safety. The men are actually con artists, who are trying to trick people into giving them money for their cause.
87. A group of men are standing on a street corner, yelling at passersby that they are in danger and should follow them to safety. The men are actually con artists, who are trying to trick people into giving them money for their cause. They are dressed as priests and actually have some holy powers to protect them from physical harm.
88. A group of men and women are standing around a large cage, which contains a large ape. The ape is naked, appears to be mad, and is picking up the men and women and throwing them at each other like they are toys.
89. A man wearing a dark cloak stands on a street corner, glaring at passersby with a look of hatred on his face. He is actually a high-level thief who hates thieves and is hoping someone attacks him so he can kill them in self-defense and then frame them for his murder.
90. A man offers to sell you a very rare and expensive sword. The sword is cursed, but the curse can be removed for 500 gp by a priest of the same religion as the original owner.

91. The man standing next to you is wearing a cloak with the symbol of a local temple. He has a silver ring on his left hand. If a player talks to him, he will offer a blessing from his god. The blessing will heal 1d12+1 HP. It will also cure disease, blindness, deafness, and remove any negative effect on a living being. If the person asks for information, he will tell them about a crime that happened in the city.
92. A man named Donovan is standing on the street. He is trying to make money by selling goods. The goods are not the best quality, and he is willing to sell them for cheap. He has 1d4 random goods that he is trying to sell.
93. A group of children are playing a game called ‘Knights and Dragons’. The game is similar to what is played in published games and modules.
94. A group of men are talking about the lack of respect that the government gives the poor people of the city. They are going to do an act of civil disobedience.
95. A merchant is selling cheap goods that are not very good quality. The merchant can be bribed with a gift of silver coins to ignore the party.
96. A man named Harold is standing on the street. He is spreading rumors about a local merchant who he believes is cheating people. He has no evidence, but he is willing to spread rumors about other merchants. He will not spread rumors about himself because he does not want to get into trouble with the local government.
97. A man named Benjamin is standing on the street. He is trying to sell a large block of marble that he has on the street. The marble is a piece of a statue that fell off of a building and broke into many pieces. The marble is worth 1d20 GP if it has not been broken into pieces. His name is Benjamin because he wants to be a great merchant like Benjamin Franklin and make his fortune in trade.
98. A man named Fargrim is standing on the street. He is trying to sell a piece of finely carved wood that he has on the street. The wood is made of a rare type of wood that cannot be found anywhere else in the world. The wood can be carved into furniture or it can be sold as a work of art. It is worth 1d20 GP if it has not been carved into furniture or artwork.
99. A group of men are talking about a local merchant who buys and sells rare goods from faraway lands at higher than market prices. They are planning to get together and buy things from the merchant and then sell them at a lower price to other merchants who live in other parts of the kingdom.
100. An elderly woman named Agnes is sitting on the street with a sign nearby that says ‘I am an elderly woman who needs help’. If players help her, she will tell them about a criminal who lives in the city. She will give them 1d6 pieces of information about the criminal, but none of them are accurate because she has lost her mind due to old age.

Remember, if you want more RPG random city encounters, head over to Random Encounters AI, another website I built. Enjoy!