I’ve put together a massive list of interesting random town encounters. If you want more, head over to Random Encounters AI. Feel free to use the encounter ideas list below in your D&D 5e campaign. It’s generic enough that you can also use it for other tabletop RPG systems like Pathfinder or even MERPs! Now, let’s get on with the random encounters in a town setting.
1) Up ahead, you see the two guards lounging about outside the entrance to the town’s tavern.
2) A man dressed in a peculiar cloak is walking down the street. He has a staff and a small bag. His name is D’nurgle, and he is selling healing potions.
3) You hear loud singing coming from a small building on the outskirts of town. A sign outside reads “The Singing Sword”.
4) You see an imposing tower off in the distance. A sign outside reads “Isaac’s Tower of Wizardry”.
5) You hear the faint sound of steel clashing on steel. Curious, you follow the noise and find yourself in the town’s training yard. A man named Sarge Thompson offers to train you.
6) A man rushed out of a house on the main street. He is cursing at someone inside the house.
7) A woman dressed in a very revealing outfit is outside walking her pet tiger.
8) A group of men are having a friendly game of dice.
9) You see a group of children playing outside. One of them is playing with a stick.
10) You see a man covered in dry mud. He is trying to get the mud off him.
11) You see a man trying to sell apples. He is mad because no one wants to buy them. “It’s only a few worms. Extra protein! I should be charging more, eh?”
12) A woman is running down the road. She looks worried and keeps glancing over her shoulder.
13) A woman walks into the town square. She is holding a large sack and trying to sell clothes.
14) A man walks up to you and tells you that he lost a gold ring. If you can find his ring, he will give you a reward.
15) A group of friends are sitting outside and playing music.
16) You see a group of children playing with a dog. The dog is running around them barking.
17) You see a man who is very upset. His horse ran off with his cart.
18) A man walks up to you and asks you to help him. A creature is terrorizing the town and he would like you to kill it. The creature is his mother in law.
19) A man walks into the town square with two large bags of flour. He is trying to sell them.
20) A woman walks into the town square. She is selling clothes. She has a few items in her cart.
21) A man walks down the street carrying a heavy looking sack. He is selling grain.
22) A group of children are playing a game. They are trying to catch a small lizard.
23) A woman is selling flowers outside the town square. She is having a hard time selling them. She is very upset about it.
24) An old man is walking down the street. He is very upset about something. He knocks over a woman’s groceries as he passes her.
25) You see a group of children playing with a cat. It has a bell around its neck.
26) You see two children playing in the street. They are having a sword fight with sticks.
27) A man walks out of a large house on the main street. He is complaining about something.
28) You see a man outside practicing his sword fighting. He looks very good. He offers to train you in sword fighting.
29) You see an old man sitting outside his house. He is trying to catch some bugs for his pet snake.
30) You see a group of children playing with a puppy. The puppy has a leash around its neck.
31) You see a man walking down the street carrying two large bags of flour. He is having a hard time carrying them. He looks very tired and upset.
32) A man walks into the town square. He is trying to sell a magic carpet. He looks very tired and upset. He has a large scar on his face.
33) You see a group of children playing with a kitten. It has a bell around its neck. The kitten transforms into a gnome wizard who runs away laughing.
34) Two men are standing outside their house talking to each other. They are arguing with each other. They are holding wooden swords. One man has a large scar on his face.
35) A group of 2d4 bards are singing a raunchy song about a local noble. When the players pass, they work them into the song.
36) The building to the right side of a side street has a sign above the door that says “No Public Restroom”. The building to the left side of a side street has a sign above the door that says “Public Restroom: 1cp”.
37) Three elven wizards (two males and a female) are laughing and walking down the street. They are obviously drunk and singing a song. The song is about their latest political enemies.
38) A man wearing a large hat is sweeping the street. He is obviously a gnome. He is angry and cursing under his breath.
39) A man wearing a large hat is sweeping the street. He is obviously a gnome. He is singing a song that his mother used to sing to him when he was a child.
40) The town crier is crying out the daily news and happenings in the town. He is crying out about the recent bandit attacks on the outskirts of town.
41) An elven wizard is walking down the street. He is wearing fine clothing and has a large staff. He looks very angry and upset.
42) A group of four men are walking down the street. They are wearing large black robes. They are carrying large wooden staffs with a large eye in the center.
43) In the middle of the main cobblestone street, five dwarves are sitting on the ground playing a game of dice. They are drunk and very angry at each other. Two town guards are nearby, quietly discussing what to do. They might enlist the party to get the dwarves to move.
44) A group of 4d6 hobgoblins are walking through the town. They are carrying large wooden shields and spears. They look very angry and are shouting at each other. On the outskirts of town, the local watch is discussing what to do. The hobgoblins have had the town under their control for the last 1d6+5 months.
45) A group of 4d6 bandits are walking down the street. They are carrying large wooden shields and swords. They are shouting angrily at each other. They look very dangerous and may attack the party.
46) A small group of halfling rogues are standing outside a tavern. They are planning a heist.
47) The clouds thicken and it begins pouring rain. All the streets become mud almost instantly, making it difficult to move.
48) Thirteen dwarven miners are walking down the street. They are carrying large axes and hammers. They are singing a song about some kind of dwarf king.
49) A drunk human is sitting on a bench in an alley. He is staring into space and looking very depressed.
50) A group of 4d6 half-elven adventurers are laughing loudly outside a tavern. They are wearing very expensive looking clothing and jewelry. They are celebrating their last adventure and are very drunk.
51) A cart has tipped over in the street. The owner is yelling angrily at everyone to get out of the way.
52) A group of 1d6+1 elven wizards are walking down the street. They are wearing blue robes and carrying staffs. They look very intelligent and may be willing to talk to the party. For the right price, they’ll point out the best places to get magic items in a 100 mile radius of the town.
53) Up ahead, a merchant stops his cart to take a drink of water. His horses are pulling the cart full of goods down the street. He offers to sell the party an assortment of items from his cart.
54) A group of 4d6 expert thieves are walking down the street. They are carrying daggers, clubs, and dark cloaks. Their faces are covered by masks. They are looking for a place to hide after they commit a crime.
55) Two dwarves are standing outside a tavern. They are arguing about who is the best looking dwarf. They are both drunk, so it will take a while for them to reach a decision.
56) A group of 1d4+1 merchants are walking down the street. They are carrying large bags of money and are discussing the best places to invest.
57) A group of 1d6+1 wood elves are walking down the street. They are carrying bows and quivers of arrows. They are hunting for some kind of animal.
58) A group of 4d6 apprentices are walking down the street. They are dressed in black robes and carrying staves. They are on their way to test their skills against each other. It looks like they are using magic.
59) A group of 1d10+1 half-orc warriors are walking down the street. They are carrying heavy axes and heavy armor. They are looking for a good fight.
60) A group of 4d6 gnomes are walking down the street. They are carrying wands, staves, and potions. They are on their way to train some new recruits.
61) A group of 1d4+1 thieves are standing outside a tavern. They are placing bets on which adventurer will fall victim to the thieves guild first.
62) A group of 1d10+1 elven wizards are walking down the street. They are carrying staffs and wearing blue robes. They look like they have a lot of experience with magic.
63) A group of 2d6 half-elves are walking down the street. They are dressed in dark clothing and carrying bags of tools. They look like they are going to rob someone.
64) A man rushes out of a shop with a merchant hot on his tail. “Come back,” the merchant yells. “You haven’t paid for the food you’ve taken.”
65) A group of people are standing outside of a shop. They are arguing about how poor the service is.
66) A man is on a stage preaching at a crowd of people. “The end is near,” he yells. “We must repent.”
67) A group of young children are skipping down the street. They are laughing and having fun.
68) A group of adventurers are walking down the street. They are arguing about which inn to stay at.
69) A mutt runs out of an alley, sniffs at a player’s leg, then begins to beg for food.
70) Two guardsmen begin to argue about who gets to keep a gold piece found on the street.
71) A street performer is juggling fire.
72) A beggar is sprawled on the ground, surrounded by empty ale bottles.
73) A group of children run out of an alley and shout, “Look! It’s the adventurers! We heard Vobna the Bard sing of your exploits!”
74) A man standing on a corner is waving a sign and shouting something unintelligible.
75) An old lady is sweeping the front step of her house. She scowls at you, but doesn’t say anything.
76) A drunk has passed out in the middle of the street.
77) A man wearing a hat is sitting on a crate, eating an apple.
78) A group of people are standing in a circle around a man playing a lute.
79) A group of children are playing tag in an alley.
80) Two men begin to argue about which way is north. They shove each other and start fighting.
81) A woman is sweeping the front step of her home and singing a lullaby to her children inside.
82) A guard is standing in the middle of the street, holding an arrow in his hands. He is staring at it in confusion. His partner is standing behind him looking equally confused.
83) Three guards are having an argument about who is the better sword fighter.
84) A man is pulling a wagon with his donkey, stacked high with barrels of ale. The poor animal is struggling to pull the wagon and the man is shouting at it to pull harder.
85) A guard is standing in the middle of the road and pointing his sword down. He shouts, “Clear the road! Clear the road!”
86) A woman is standing by the side of the road looking up at the sky. She shouts, “Dinner is ready! Come and get it!”
87) A shopkeeper is sweeping the front step of his store and muttering to himself.
88) A couple of guards are standing in front of a dark alleyway. They are discussing what they will do if they catch the thief who lives in there.
89) A woman is running down the street trying to hold onto her skirt. Two other women are chasing her yelling, “Thief! Thief!”
90) A man has stopped in the middle of the street and is looking up at the sky. He shouts, “I’m on top of the world!”
91) Three drunk men are stumbling down the street, singing about the beautiful women in town and how they are going to go home and have a good time with them.
92) A man is loading a wagon with barrels of ale, when another man runs up to him and demands he pay for his drinks. He points to a barrel and shouts, “That one over there! You can’t sell that one. She’s my favorite!” He then cackles and runs off.
93) Four guards are trying to pull a giant tree out of the middle of the road. A wizard (who is now not welcome in the town) caused it to sprout. Players can find the wizard later somewhere outside of the town.
94) A man is holding a fistful of flowers and crying.
95) A woman is sitting on the side of the road, crying and holding a shoe in her hand.
96) A man is walking down the street with a large book under his arm. He is mumbling to himself and pointing at various buildings.
97) A man is shouting to his wife through the window of their house, “What did you spend all my money on?”
98) Four men are sitting outside an inn, singing a song about how awesome their drinks were last night.
99) An old man is wandering around town, muttering to himself and pointing at various buildings.
100) A couple of guards are standing in front of a manhole cover. They look worried and keep glancing down the hole and then up at the sky.
Thanks for reading my list of random town encounters for D&D 5e. These are basic ideas that are meant to be fleshed out by you, the DM. Please feel free to use these in your games and to modify them to fit your world. If you have any ideas or additions to make this list better, find me on Twitter and let me know!