Random Encounters on the Road: DND 5e+

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I’ve put together some lists of random encounters on the road for your fantasy tabletop RPG campaign. If you like the list, feel free to use it in your campaign. At the end of the random table, I have information on a few AI-powered RPG tools I’ve created that can also help you with your campaign. Some of them are free! First, let’s get to the random road encounters.

D100 Random Encounters on the Road

  1. A group of traveling merchants are selling a new type of cloak that is made of a material which repels rain, mud, and snow and protects the wearer from the cold, no matter how severe. The merchants are looking for adventurers to test the cloaks and report back to them. All cloaks will be given to the players for free, but only if they agree to wear them and report back to the merchants about how well they work in different types of weather.
  2. A group of farmers are offering to sell players a herd of three hundred sheep for twenty-five gold pieces. They look healthy and well-fed. The farmers want to sell the sheep quickly and will not haggle with the players or accept any offers that are lower than twenty-five gold pieces per sheep. The farmers will not accept any offers that are lower than twenty-five gold pieces per sheep.
  3. A group of farmers are offering to sell players a horse for twenty gold pieces. The horse is in good condition and looks like a good riding horse. The farmers will not accept any offers that are lower than twenty gold pieces per horse.
  4. A group of farmers are offering to sell players a mule for ten gold pieces. The mule is in good condition and looks like a good riding mule. The farmers will not accept any offers that are lower than ten gold pieces per mule.
  5. A group of farmers are offering to sell players a pig for two gold pieces. The pig looks healthy and well-fed.
  6. A group of farmers are offering to sell players a cow for three gold pieces. The cow looks healthy and well-fed.
  7. A group of farmers are offering to sell players a goat for one gold piece. The goat looks healthy and well-fed.
  8. A group of farmers are offering to sell players a chicken for one copper piece. The chicken looks healthy and well-fed.
  9. A group of farmers are offering to sell players 3d6 apples for one copper piece each. The apples look fresh and delicious.
  10. A group of farmers are offering to sell players 3d6 onions for one copper piece each. The onions look fresh and delicious.
  11. Lame donkey with a sign on its back that says, ‘Don’t laugh.’
  12. The sound of a thunderstorm can be heard in the distance.
  13. A group of farmers are in the middle of a heated debate over whether the local orc attacks are caused by wolves or wyverns.
  14. A travelling bard is singing about one of the following topics: The king in Red, a local noble, the goddess of thunder, or a nearby temple.
  15. A group of men are having a contest to see who can throw a stone the furthest.
  16. A group of men are having a contest to see who can run the fastest without shoes.
  17. A group of young boys are playing a game where they try to knock each other off of a log by swinging at each other with sticks.
  18. A man is trying to sell a recently caught hare but no one wants to buy it because it’s still alive. He’s trying to convince people to buy it by saying that it’s been trained to dance and perform tricks on command.
  19. A woman is trying to sell a decorative shield that she made by carving into it various designs and pictures.
  20. A group of men are having a contest to see who can drink the most ale without getting drunk.
  21. Xorn. A 1d4 level Xorn is foraging for food. They will not attack unless provoked first. They will run away after a few rounds if attacked. They are from another plane and are not from this world. They are on a mission to deliver a message and they are not connected to the road.
  22. Two men and their horses have been attacked by a group of bandits. They need help. The bandits are still nearby. They are hiding in the woods.
  23. A group of children are playing hide and seek with each other while they wait for their parents to return home.
  24. A trader has set up a roadside stand and is selling supplies to people as they pass by.
  25. A group of men and women are standing by the side of the road. They are looking for work.
  26. A man is sitting on the side of the road holding a small box. He is holding it tightly and he does not want to let it go.
  27. A couple of men and women are sitting by the side of the road. They are looking for work.
  28. A couple of men are sitting by the side of the road. They are looking for work.
  29. A couple of men and women are standing by the side of the road. They are looking for work.
  30. A man has set up a roadside stand and is selling supplies to people as they pass by. The man at the roadside stand looks like a female dwarf but is actually a disguised male half-dwarf. He is selling supplies at a very high price to anyone that comes by. He is hoping to make some money because he was hired by other players earlier in the adventure. He is still getting used to his disguise and he is a little nervous that he will get caught.
  31. Koopa Troopa with a dead horse. The horse carcass has been torn and eaten by a large bird or creature. The koopa troopa is distressed. He tells the players that he saw a large bird attacking the horse. He tried to intervene, but the bird attacked him, too. He believes the bird is a pterodactyl.
  32. A group of 3d6 farmers are heading to the nearby village. They are worried about the recent disappearance of their livestock.
  33. A group of 2d6 farmers are heading to the nearby village. They are worried about the recent disappearance of their children.
  34. A group of 2d6 villagers are heading to the nearby village. They think someone has been hitting their horses with magic.
  35. A group of 3d6 soldiers are heading to the nearby village. They have been given orders by their king to capture a group of troublesome criminals.
  36. A group of 2d6 soldiers are heading to the nearby village. They have been given orders by their king to capture a group of thieves.
  37. A group of 2d6 thieves are heading to the nearby village. They have been given orders by their king to bring back a group of hostages.
  38. A group of 2d6 villagers are heading to the nearby village. They have been told that a large, red dragon is terrorizing the kingdom.
  39. A group of 2d6 villagers are heading to the nearby village. They have been told that a large, red dragon is terrorizing their village. They are carrying large rocks and pieces of wood to fix their homes after the dragon passes through.
  40. A group of 4d6 villagers are heading to the nearby village. They are carrying large rocks and pieces of wood to fix their homes after the dragon passes through. They also bring news that a large, red dragon has been terrorizing their village.
  41. Lumbering through the road is a lumbering, tall creature wearing a red cloak. The creature looks like a giant. The creature is lumbering through the road. The creature is headed north. The creature is carrying a large warhammer and wearing a large shield.
  42. Players see an old man and woman sitting together on a stone wall. The man and woman are holding hands. The old man and woman are using their other hands to hold each other’s shoulders. The old man and woman are facing each other and their heads are touching.
  43. A wagon with a large sail painting of a fish is being pulled by a large horse. The wagon is being driven by a man who looks like an elf.
  44. Small birds land on the shoulder of the road. A few moments later, they fly away.
  45. A group of boys and girls are playing tag and running around a small stone building.
  46. A group of men are sitting around a campfire. The men are telling stories about the nearby abandoned castle.
  47. A group of men and women are sitting around a small campfire. The women are fending off the men. The men are wearing black cloaks and hoods. They look like cultists.
  48. A man is sitting on a large stone wall. The stone wall is made out of stone blocks. The stone blocks look like they were put together by masons. The man is holding a large red cloak in his lap. The cloak looks like it was made by a tailor. The man is looking at the cloak and crying. The man looks like he is going to throw the cloak in the road if someone doesn’t stop and talk to him.
  49. A group of men and women are standing around a campfire. The men and women are holding hands and singing songs about hunting.
  50. A group of men and women are standing around a campfire. The men and women are holding hands, talking, and laughing. The men and women are dressed in leather armor and holding small shields and wooden clubs.
  51. Jugglers and dancers from a local traveling circus are having a picnic along the side of the road. They are preparing for their next performance.
  52. A man is walking down the road. He is singing loudly. He is drunk.
  53. A woman is walking down the road. She is singing loudly. She is drunk.
  54. A farmer is walking down the road. He is carrying a large sack over his shoulder. He is headed to the market to sell his goods.
  55. A group of children are playing a game of tag along the side of the road.
  56. A shepherd is leading his sheep to a nearby field to graze. The sheep are bleating loudly as they are being led down the road.
  57. A group of hunters are walking down the road. They are talking about their recent hunting trip. They are carrying a large buck over their shoulders.
  58. A man is walking down the road. He is singing loudly. He is heading to the nearby village to get drunk.
  59. A group of men are walking down the road. They are talking about the recent theft that occurred in the nearby village. They are discussing who they think stole from the village. They are headed to the nearby village to get drunk and forget their troubles.
  60. A group of children are playing a game of tag along the side of the road. They are laughing and having a good time.
  61. K, a level 1 dwarf, is sitting on the side of the road playing a lute. He is looking for an audience with one of the nearby kings. He is a bard. He will sing for food.
  62. A man is standing in the middle of the road. He is wearing a large coat. He has a large sack on one of his shoulders. He is standing on one foot. He is dancing. He is drunk.
  63. A merchant has set up a cart.The merchant is selling ale. The merchant is also selling a slightly used suit of plate mail armor. The merchant will trade the armor for a cart or a horse.
  64. A man is standing in the middle of the road. He is holding a small sign that says ‘Need Help.’ He says that he has been robbed and his horse has been killed by a group of goblins. He will pay the players in gold.
  65. A man runs out of a house and stands in the middle of the road. The man says that he has been robbed by goblins.
  66. A man and a woman are standing in the middle of the road. They are arguing with each other. The man is drunk or on drugs.
  67. A man and a woman are standing in the middle of the road. They are arguing with each other. The woman is a witch.
  68. A man is sitting on the side of the road. He is holding his nose. He states that he has been robbed by a group of goblins. He says that they stole his cart.
  69. A man is sitting on the side of the road. He is holding his nose. He states that he has been robbed by a group of men.
  70. A man and a woman are sitting on the side of the road. The man states that they have been robbed by a group of men. The man says that they stole their cart, their horses, and their gold. The woman doesn’t talk. She’s actually been kidnapped by the man and wants help.
  71. Wagon being attacked by 2d6 wolves: The wolves are old and weak, but they come in great numbers. They’re hungry and smell the food the players are carrying. They will attack the players first, then try to eat their horses and their food when the horses are dead.
  72. A drunk man staggers to the side of the road and offers the players his last bottle of wine.
  73. A merchant is selling rare and valuable items.
  74. A merchant is selling rare and valuable items, but he is a thief and doesn’t have any items to sell. He will ask for a sample of the party’s gold before he will do any business with them.
  75. An old man is walking down the road. He is lost and looking for his home. He will ask the players for directions to his house.
  76. A group of children are playing in the street, making up a game as they go.
  77. A group of children are playing in the street. They are pretending to be soldiers fighting off an orcish attack.
  78. A group of men are standing along the side of the road. They are discussing the war. Their opinions differ greatly.
  79. A group of men are standing along the side of the road. They are discussing the price of grain. Their opinions differ greatly.
  80. A group of children are playing in the street, making up a game as they go.
  81. Unexpected but interesting sight. There is a carriage with no horses but two skeletons pulling it. Inside the carriage, there is a treasure chest. The skeletons will attack the players.
  82. A man dressed in rags begs for food. Players can choose to give him food or not. He will persist even if players don
  83. ike a madman. If players give him food, he will say he is a king who was cast out. He will ask for help. If players give him food, they will fight his soldiers. If they don’t, he will attack them!
  84. A group of children are playing in the road. They are laughing and having a good time.
  85. A group of men are praying in the middle of the road. They are praying for their village to be blessed with good crops and plentiful fish.
  86. A group of men are singing in the middle of the road. They are singing a song about a battle that took place in the area.
  87. A group of men are talking in the middle of the road. They are talking about the strange happenings in their village. Their village is plagued by strange noises at night.
  88. A group of women are gossiping in the middle of the road. They are talking about an upcoming marriage.
  89. A man dressed in rags is begging for food. Players can choose to give him food or not. He will persist even if players tell him he has enough food. He will say he has nothing to eat and he is starving. If players give him food, they will fight his guards who have been following him and observing the party’s actions.
  90. A group of men are talking in the middle of the road. They are talking about an upcoming war with a neighboring country.
  91. Hirelings – 1d4 of a random hireling are traveling down the road. They are headed to a nearby city.
  92. The road ahead is blocked by a fallen tree. A group of 1d6 commoners are trying to remove it from the road. They say it was caused by a group of 1d4 halflings who passed through earlier. The halflings were headed to a nearby city.
  93. You are stopped by 1d4 guards. They say they are looking for a group of 1d4 halflings who were headed to a nearby city.
  94. A group of 1d4 hunters are hunting for game. They say they saw a group of 1d4 halflings headed to a nearby city.
  95. A group of 1d4 hunters are hunting for game. They say they saw a group of 1d4 humans headed to a nearby city.
  96. A group of 1d6 commoners are heading to a nearby city to sell their goods. They say they saw a group of 1d4 humans headed to a nearby city.
  97. A group of 1d4 elves are traveling down the road. They are headed to a nearby city. They say they saw a group of 1d4 humans headed to a nearby city.
  98. Two adventurers are sitting on the side of the road. They appear to be injured. A group of 1d4 humans passed by earlier and attacked them. They say they were headed to a nearby city.
  99. A group of 1d4 humans are heading to a nearby city. They say they were searching for a group of 1d4 halflings who passed through earlier and attacked them.
  100. A group of 1d4 halflings are sitting on the side of the road. They appear to be injured. A group of 1d4 humans passed by earlier and attacked them. They say they were headed to a nearby city.

100 Random Roadside Encounters

Psst. Hey, buddy. Need some roadside encounters for your D&D campaign? Keep reading. I’ve got d100 worth below, and a secret, free website where you can get thousands upon thousands of fantasy encounters in dozens of locations. First, though, here’s my list of 100 Dungeons and Dragons roadside encounters. Feel free to use them for Pathfinder or other game systems!

1) You see a cart moving against the flow of traffic. Guards with crossbows stand on the back of the cart.

2) A man walks briskly along the road and shouts, “Let him go! Let him go!”

3) A group of peasants ambush a merchant and attempt to rob him.

4) A farmer carrying a huge cabbage watches you as you walk by.

5) A group of goblins attempts to ambush you.

6) The road is blocked by a fallen tree.

7) A man is hanging from a tree by his feet. He is dead.

8) A band of brigands attempt to ambush you. They have one hostage.

9) A magical signpost stands in the middle of the road. It reads, “Take the road on the left and avoid the road on the right.”

10) A woman is beating an ox with a stick. She shouts at it, “Pull, you dumb animal! Pull!”

11) A row of four beheaded bodies stretches across the road.

12) A man pulls a cart containing four gallows. Four executed criminals hang from the gallows.

13) A group of lepers walk along the road begging for food and coin.

14) A group of young, scantily clad women sing and dance provocatively in the middle of the road.

15) An old man spits on you as you walk past.

16) A priest of a random god hands out pamphlets to passersby. He is loudly proclaiming that all who do not follow his god will burn in hell.

17) A beggar asks for coin. His voice is that of a woman. He is actually a shameless transvestite.

18) An old woman asks for food. She strikes up a conversation and offers to tell your fortune.

19) A group of farmers argue over who owns the cow that one is attempting to lead away.

20) The road collapses into a sinkhole.

21) The road is blocked by an overturned wagon. On the ground beside it, you find the body of the wagon’s driver.

22) A pig is running across the road.

23) A guard blocks the road and demands a toll.

24) A young child throws stones at you.

25) An old woman yells at you, “You’re a thief! I heard your friends saying that you would rob someone today!”

26) You see a group of 10 armed men staring at the ground in the middle of the road. It looks like they are waiting for something.

27) Two women in peasant clothes are arguing. One accuses the other of trouble-making.

28) A group of dwarves are eating and drinking in the middle of the road. They invite you to join them, but warn you not to drink any of their ale or wine.

29) Four guards ask you to pay a toll to pass through a town. They claim that they need to raise money to fund the town’s defense.

30) A bandit holds up a merchant and asks you to pick which pocket his dagger will be found in. The merchant, however, informs the bandit that he is an undercover guard who was hired to test the bandit’s skills by catching him in the act.

31) A group of young men are fighting over a young woman.

32) A group of children throws stones at you.

33) A group of children (1d6 + 3) are playing in the middle of the road.

34) A man and a woman argue loudly about his poor driving.

35) A merchant offers to sell you a “lucky” trinket for 10% over cost.

36) A clairvoyant woman gives you your fortune for 1gp. She has seen a great change in your fortunes in the future.

37) A child begs for food, then runs into the woods once he has what he wants.

38) A man is lying on the ground moaning. He holds a bloody wound in his belly and begs for help.

39) An old, abandoned building catches fire and burns to the ground.

40) The road is blocked by a fallen tree.

41) A group of men playing cards stand around a card table set up on the road. They invite you to come play a game with them. They are actually highway robbers who use the card games as a ruse to attract victims. They attempt to rob you.

42) A drunken man is walking towards you. He trips and falls into a filthy, water-filled ditch. He curses at you and returns to his feet.

43) A horse is laying in the middle of the road. It has broken its leg in a trap.

44) Two young, drunk men are fighting over a local girl. They call her insulting names and call each other names.

45) A boy runs out of the woods and begs you to buy his plums.

46) A child on the side of the road is crying and holding his hand.

47) A merchant offers to sell you a “lucky” trinket for 10% over cost.

48) A group of peasants argue about how to divide the loot from the robbery they just committed.

D&D Roadside Encounters
D&D Roadside Encounters

49) A group of men dressed in animal skins run out of the woods and scream like animals at you.

50) A man offers to sell you a pet for a very low price. He asks you not to tell anyone where you got it.

51) A man screams out in agony behind the tree line. A goblin has him pinned to the ground and is attempting to saw his leg off.

52) A man and a woman are arguing in the road. She accuses him of cheating on her and demands that he confess or she will never speak to him again.

53) You see a woman in peasant clothes holding a baby. She begs for food, shelter, and coin (50% chance she is faking it).

54) A man throws trash at you.

55) The road is blocked by a fallen tree.

56) A group of peasants are digging a large hole in the road. They ask you if you want to help. They are actually digging a hole to bury a dead body.

57) A man approaches you and offers to sell you some stinky cheese for 1gp. It smells awful, but actually heals 1d4 hp when eaten.

58) A man asks you for directions to a nearby town. He actually wants you to lead him there, so that he can rob you as you sleep.

59) A merchant approaches you and offers to sell you a very rare item. If you buy it, the merchant will disappear into the woods and never be seen again.

60) A group of peasants are throwing stones at a group of merchants standing on a wagon. The merchants want you to help them fight off the peasants. The peasants want you to help them kill the merchants.

61) You hear baying in the distance. A pack of wolves are chasing a man down the road towards you.

62) A group of men are sharing stories of how they each got into a fight with a dragon. None of them believe each other.

63) A farmer on a donkey is leading a cow down the road. The cow’s leg is bandaged and splinted.

64) A small child runs up to you, holding a very dirty piece of paper and says, “Daddy says I have to give you this.” The paper is empty. The boy runs away.

65) A group of peasants are trying to push a wheelbarrow carrying an old man down the road. The old man is cursing profusely and spitting at people.

66) A farmer comes running up to you, holding his stomach and screaming. He is being chased by a pig.

67) A woman in the road cries out that she has been robbed. She is holding out a bag of copper pieces and claiming that it is platinum.

68) A wagon filled with hay passes by. Inside the hay, you see a man fighting off a group of rats.

69) A glass bottle flies over your head, breaks on the ground and starts spilling black liquid everywhere. A wizard named Joe approaches you, promising to pay for any damages from the demon he’s just let loose.

70) A wizened old man in rags approaches you and asks for some of your food. He asks you to follow him into the woods to meet his friends. He’s a bandit looking to ambush the party.

71) A group of peasant women are hiding in bushes on the side of the road. They jump out and start beating on the party, crying out that they are being attacked until two men dressed in town guard uniforms rush out of the forest to save them. They’ll accept a bribe.

72) A man in an apron approaches, carrying a basket of vegetables. He claims that he has just been mugged and demands that you help him catch the thief. He’s actually the thief and wants to sell you stolen vegetables.

73) A man approaches you and asks for directions to a nearby town. He was actually employed by a local farmer who wants you to bring him to the city so he can steal the farmer’s riches.

74) A farmer is surrounded by chickens in the middle of the road. They beg you to take them off his hands and to make sure he doesn’t eat them.

75) A man approaches you, and tells you that he can help you find a hidden treasure if you lead him to it. He is actually a bandit who will steal your treasure.

76) A man in leather armor is standing in the road with his hands tied behind his back. As you approach, he tells you that he has been captured by brigands, who are holding his family prisoner until he tells them where the treasure is buried. The man is lying. He’s bored and trying to find people to interact with him. His name is Thom.

77) A man asks for your help digging up a treasure. You have to take a secret path through the woods to reach the treasure. The treasure is actually a keg of ale buried in the woods.

78) A man dressed in bright colors offers to give you a “magical item.” He gives you a fake. It is a wand with a feather on the end.

79) A man offers to sell you a miracle drug. It’s actually a poison that will kill you in one day.

80) In the distance, a man screams that he is being robbed by bandits. When you approach, the bandits run away, dumping the man’s sack of supplies on the ground. The man named Frank is thankful and rewards the party with some items.

81) A man is selling a fine horse for an unusually low price. He is actually trading stolen horses with the highwaymen he’s in league with.

82) A man offers to give you a “free” item. It is a cursed item. The man will run away.

83) A man in a dark robe approaches, claiming to be a powerful mage. He is actually an illusionist and has put everyone around you to sleep with a wand. He is studying their dreams.

84) A man in masterwork armor is standing on the road, shouting at passersby that they are cowards and should join his mercenary company, The Mary Brigand.

85) A band of brigands attack. They are actually farmers protecting their crops from bandits and have mistaken the players for bandits.

86) A group of peasants are huddled together, praying to their god for rain. They ask you to join them. One of the men has a tattoo on his arm.

87) A group of peasants are carrying a long pole between them. On the pole is a dead boar.

88) A merchant approaches, offering to sell you some “exotic food” for half the normal price. It is actually poison.

89) A man who claims to be a priest of the local god leads you into the woods with a shovel. He has been instructed to dig up something hidden there.

90) A group of peasants are washing their clothes in the local stream.

91) A man in rags is sitting in a tree and begging for a copper. He will follow you for 1 mile and beg for copper pieces until you run him off.

92) A wagon filled with hay passes you by. There are dead bodies concealed among the hay.

93) A man stands and shouts to the sky, cursing his fate. He is actually the mayor’s son, sent into the woods to die. The bandits stole his armor and he can’t even go home. The party needs to help him regain his honor.

94) A group of old men from a nearby village are carrying a coffin down the road. They are hunting for a vampire.

95) Two men arguing in the road. One is insisting that the other man owes him money and is refusing to pay. The other man has his sword drawn and says he’s going to end this once and for all.

96) A man is sobbing by the side of the road, holding his dead wife in his arms and begging for help. She has a sword in her back. The man is crying because he killed his wife. Guards soon come and take him away.

97) A man on a donkey is carrying a cage with a small monkey. He’s a merchant who is trying to trade the monkey for a chicken.

98) A man is standing in the road, smiling, waving and saying hello to everyone who passes. He has no tongue.

99) An old woman is found wandering the road, talking to herself and singing. She has been cursed to see her life play out in hallucinations.

100) A man is sitting on a rock, sick from a wasting disease. He was part of a noble family, but has no money to pay for healing.

100 Mid-Level Random Road Encounters

Here’s a list of 100 mid-level random road encounters for your fantasy tabletop campaign.

1) The road ahead splits into two, and you find a bearded old man sitting by a small campfire beside the road. He introduces himself as an ancient hermit and says he’s been waiting for adventurers to come by and help him with a problem, and offers you a reward if you’ll listen to his story. He needs the players to kill a mid-level bandit nearby who killed his son. If players accept, he will not be able to pay them in material possessions, but he will help them with information about the local area.

2) A large tree blocks the road ahead. It will take the players 2d6 hours to clear a path through the tree. While they’re working, they hear a noise coming from nearby. A group of 2d10 gnolls with war hounds approach and attack the players.

3) The road is flooded. A local mage was practicing water magic and unleashed a raging torrent of water onto the road. The players have to find a way across or wait for it to recede.

4) A local farmer asks for help with a pair of hill giants who have been killing his cows. He says he’ll pay the players 500 GP if they catch the hill giants and bring them back alive. The hill giants are hiding out in a nearby cave that has been accidentally twisted into a maze by the local elves. There’s a good chance the players will get lost in the cave. This regularly happens to the two hill giants whose names are Tagg and Jagg. Players can peacefully persuade the hill giants to return the cows (they like the milk and use the cows to navigate the maze), or they can try to kill the hill giants.

5) Up ahead, the sound of drums and chanting can be heard. The players approach a campfire with a group of humans around it. They’re dancing and chanting in unison, and they look like they’re all having fun. The players can join in the festivities by the fire, or they can stand on the sidelines and watch.

6) The players can hear a man shouting for help. He’s trapped under a fallen tree. The players can choose to help him, or they can ignore him.

7) Three centuar warriors approach and demand payments for the players to use the public road they’re on. If players refuse, the centaurs will run away then attack with long bows.

8) An old man is stumbling along the road. As players approach, he will beg for help. If players help him, he will attempt to steal something from the players.

9) Two children are playing tag along the road. They will run off if players approach.

10) The players hear a woman weeping softly. When they approach, they find a woman whose husband ran away. Her name is Ammara and she will try to seduce any single male players. She will not give up and she will follow the players for as long as it takes to get their attention.

11) The players approach a group of dwarves sitting around a campfire. They will not talk to the players and will instead throw rocks at them.

12) The players come upon a group of tribesmen who are preparing their weapons for war. Their chieftain has been rampaging through the valley and has killed many of the tribesmen. The tribesmen will attack the players if they’re not of their tribe, and will attack each other if they’re of the same tribe.

13) The players come upon a camp with a very large and heavy-looking wagon. The camp is abandoned, and the players can search the wagon and the surrounding area for treasure. One item of note is a large orange gem on a necklace. The necklace is cursed and will attract the attention of a nearby group of demons. The demons will attack the players as they’re moving the wagon away from the camp, and the players will have to fight them as they try to move the wagon down the road.

14) A small boy is sitting on the side of the road, sobbing. He is missing his pet cat, which ran away. If players find the cat, they can return it to the boy. He’s the prince’s son and they will be rewarded handsomely.

15) The players find an old man sitting beside the road. He is selling delicious honeycakes. If the players ask, he will tell them that he runs an orphanage in town and can offer them warm beds to sleep in. He will take the players to the orphanage, but here the players will be attacked by an assassin.

16) A member of the Thieves’ Guild is standing on the side of the road, holding a map and looking confused. There is a large X on the map, and the Thieves’ Guild member thinks the players might know where the treasure is. He will pay them 1d10 GP if they can show him where the treasure is. If the players accept, the treasure is actually the location of a nearby bandit camp where players will be ambushed by 2d8 bandits.

17) The players come across a very old man sitting by a campfire. He is a sage and will trade information for a small token of his choosing.

18) The players come across a group of children singing a song about a local hero. It’s a love song. If the players approach, the children will run away.

19) Two old women are sitting on the side of the road, selling some of their possessions. Their names are Marge and Jenna. They are very friendly and will offer some of their goods to the players. If the players accept, the old women will attack them. They are actually werewolves who are testing to see if anyone can resist their charm.

20) A group of local thugs are on the side of the road, looking for some easy prey. The players can fight them or run away.

21) A group of townspeople are dragging a box down the road. They are transporting the box to the town’s richest man. If players help, they can receive a reward of GP or information about the area.

22) The players come across a group of three men fighting over a golden ring. They will fight to the death over the ring, taking no notice of any players who are watching them.

23) A group of peasants are hauling a large wagon down the road. One of the wheels is broken and it’s making a racket as it moves. This will attract the attention of 2d6 bandits.

24) A group of men and women in fancy clothes and carrying parcels and boxes approaches the players. They’re in a hurry and will not stop for any reason. If players try to stop them, they will summon guards and run away.

25) The players find a group of heavily armed men wearing the uniform of a local noble. They are traveling under the noble’s protection. They will not let the players pass, even if the players are on the noble’s business.

26) Just as rain begins, making the road a muddy mess, a pack of 4d4 trolls shuffle onto the road and attack.

27) A group of halflings are sitting on the side of the road, eating. They are on their way to a festival. They are willing to share their food with the players if the players are willing to eat it right there. Their names are Bud and Squeak, and they are very friendly.

28) A man dressed in black robes, wearing a black cloak and carrying a hooded lantern approaches the players. He asks them to help him carry something to the nearby town. If the players help, they discover they are carrying a coffin. The man’s name is Mortis and he is a necromancer. He will not attack the players if they are friendly. If they are hostile, he will attack them with two 1st level skeletons.

29) A woman is sitting on the side of the road. She has a package with her, and she seems to be crying. Players can ask her what’s wrong, but she will not answer. She will not attack the players. If the players try to sneak up on her, she will attempt to hide the package. She will not even give her name.

30) A small group of people are gathered around a young man who is lying on the ground. They are tending to his wounds. They are all wearing dark clothing or robes, and they are all slightly pale. They will not let the players approach, and they will flee when the players attempt to question them.

31) The sides of the road are littered with dead animals. If the players search, they will find that the animals were killed with magic. If the players approach, they will be attacked by 2 mages.

32) The players hear a woman crying. They find two women standing by the side of the road. One is old and the other is young. If the players ask, they will tell them that their baby is missing. If the players agree to help, they will find the baby in a nearby tree. It is a baby griffin, and it is being attacked by a group of griffins. The griffins will fly away once they have killed the baby griffin.

33) The players come across a hunter with a dead animal slung over his shoulder. If the players approach, he will ask for directions to a nearby town.

34) A wizard wearing a black robe is sitting in the middle of the road. He is researching, and he will attack without warning the players if they get too close.

35) A group of women are cooking dinner beside the road. They are on their way home from work. They will share their dinner with the players if the players ask.

36) A man in a red robe is sitting on the side of road. If the players approach, he will tell them that he has stolen a valuable item. He will offer to sell it to the players for 1d6 x 10 GP.

37) A group of men are gathered around a campfire. They are drinking and celebrating. They will welcome the players to join in. They are celebrating the harvest, and they will invite the players to join in.

38) A group of men are lying on the ground, sleeping. They are members of a local militia and they are exhausted after a long day of training.

39) A group of men and women is traveling down the road. They are singing and making a great deal of noise. If the players approach, they will attract the attention of 2d4 wolves who will attack.

40) The players find a dead man with a note pinned to his chest. If the players take the note, they will discover it’s instructions for a meeting with the leader of a local thieves’ guild.

41) The players find a group of children playing in a field. If the players approach, they will scream and run away. If the players follow, they will find a circle of mushrooms in the middle of the field. If the players eat these mushrooms, they will become invisible and be attacked by 2d4 pixies.

42) The players see a man in a black robe standing beside the road. He is holding a lantern and bleeding from a wound on his leg. If the players approach, he will ask for help. He will attack when the players get close. The man is a mid-level rogue who was hired to kill the players. He has a Ring of Charm that he will use to sway the battle to his side.

42) Three men are sitting on the side of the road. They are selling the contents of their wagon. If the players approach, a fight will break out. They are bandits.

43) 3d4 people are sitting on the side of the road. They are poor and they’re waiting for a caravan to come buy their goods. They will offer the players a chance to buy their goods.

44) The players come across a group of peasants singing a song about a local, cruel noble. If the players approach, the peasants will stop singing and run away.

45) A group of 2d20+12 giant rats (diseased) rush from a nearby field and attack the players.

46) The sounds of thundering footsteps can be heard from a nearby cave. A group of 12d6+12 orcs come rushing out of the cave to attack the players.

47) The players find a group of people standing around a camp fire. They are dancing and celebrating. If the players approach, they will invite them to join in. They will ask them to remove their boots and join in barefoot. This is a ruse. If the players remove their boots, the others will laugh at their expense then tell them to go away.

48) The players hear the sound of a man screaming for help. If the players search, they will find a man being attacked by a displacer beast. The man has a bag of 100 gp on him.

49) A group of people is running from a group of 1d8+3 ogres.

50) A group of merchants is selling their goods from a wagon. If approached, they will attempt to sell the players a random magic item for 10x the normal price. They are scammers.

51) Four half-giant warrior barbarians are riding along the road in the opposite direction. When they reach the players, they will ride past without acknowledging them.

52) A group of 2d4 soldiers are building a pyre. They are preparing to burn a man being held prisoner. If the players help, they will be able to save the man.

53) A group of 2d4+1 soldiers are searching the area for a missing person. If the players help, they will discover that the person they are searching for is the leader of the soldiers.

54) Several odd noises can be heard from a nearby patch of bushes. They are sounds of 1d4+2 giant rats eating the remains of a dead body. While players are dealing with the rats, a tribe of gnolls will arrive and attack the party from behind.

55) Overhead, several crows are flocking. If the players investigate, they will find a man’s body in the middle of the road. He has been brutally murdered.

56) The players hear the sounds of a battle being fought nearby. If approached, they will find a group of 2d10+10 warriors fighting 2d6+6 ogres. If the players help, they will discover that the warriors are all women. They are part of an all-female tribe that was being attacked by ogres.

57) A group of people are using a wagon to build a wall. They are using rope and boards. If the players help, they will discover that the wall is being built to keep out a baby black dragon that has been terrorizing the area.

58) The players hear the sounds of wild horses. If the players investigate, they will discover a black horse racing towards the party. If the horse reaches them, it will bow to their feet. The creature is very intelligent and will only allow a lawful person to ride him.

59) Four men are standing on the side of the road. They are drunk and they will begin to fight each other.

60) A man is standing on the side of the road. He will ask the players for help. He will tell them about a nearby man who has been beating and abusing his wife and daughter. The players will rush to the man’s home and find it abandoned. If searched, the players will find a note from the man. He will explain that he was forced to move and that the woman and her daughter were killed by undead. The house will be haunted by the women’s ghosts. They will attack whoever enters the cabin.

61) Two elven rangers are standing on the side of the road. They have eight wolves with them. They are recruiting for a local mercenary company.

62) Fourteen smelly barbarians attack!

63) Players see an abandoned wagon on the side of the road. If they investigate, it will attack. It’s a mimic.

64) Three boulders block the road. If the players remove the boulders, they will discover they are actually stone elementals.

65) A group of 6d4 men are standing on the side of the road. They are protecting a group of baby ducks. If the players try to take the ducks, they will fight the players.

66) A group of men with red robes and swords under their cloaks are standing on the side of the road. If the players approach, they will attack. They are a cult that has been terrorizing the area and can be found anywhere in the wilderness. They are led by a mid-level priest with a Ring of Invisibility and a Rod of Healing.

67) A group of 2d6+12 troglodytes rush from the woods and attack the players.

68) A group of 2d4 men is standing on the side of the road. They are holding a sign that says: “Help us!” If the players approach, they will ask for food. If the players give them food, they will demand gold. If the players give them gold, they will demand silver. If the players give them silver, they will demand jewels. If the players give them jewels, they will demand magic items. If the players give them magic items, they will ask the players to join them in fighting a nearby dragon. If the players join in fighting the dragon, they will receive 10x the value of what they gave away.

69) Sounds of battle can be heard coming from a field to the left of the road. It is a group of barbarians fighting a group of elves. The players can help either side or neither.

70) Up ahead, players spot a creature that looks like one of the party members. It accuses the party member of being an imposter. This is a doppelganger.

71) A vampire bat descends and transforms into a vampire that attacks because he is bored and hungry for blood.

72) A necromancer with an army of 2d20 zombies and 2d20 skeletons is marching toward the players. He will stop and demand a token of appreciation. If he’s given anything under 100 gp value, he will attack. If he’s given over 100 gp value, he will thank the players for not being stupid and leave.

73) The road ahead widens unnaturally. If anyone walks on it, the road will attack. It’s a mimic.

74) Three giant eagles attack from above.

75) A group of 2d8 soldiers led by a veteran warrior who has a magical sword and a magical suit of armor is standing on the road. They are traveling to a local city to join the army.

76) The players hear a chorus of beautiful singing. It is a group of sirens trying to lure people to their deaths.

77) A wizard is riding a magic carpet along the road. His name is Earlghan the Great. If players top him, he will offer to sell them his carpet for 5,000 gp. If the players refuse, he will attack.

78) A group of 2d4 goblins are standing on the side of the road. They are offering to sell the players 2d4 wolf pups for 75 gp each.

79) A group of 2d4+2 bandits are standing on the side of the road. They will ask the players for food and gold. If the players refuse, they will attack.

80) Two old men stumble along the road, arguing loudly with each other. They will approach the players and beg for food. They will attack the players if they don’t get any. The two men are ghouls in disguise.

81) Up ahead, the road narrows and splits. They will discover a skeleton that has been smashed to pieces. A giant turtle is nearby. It will ask the players for food. If the players give the turtle food, it will ask them to help it fight a nearby witch that turned him into a turtle.

82) Several dozen men and women are standing on the side of the road. They are begging for food and money. They are members of the Cult of Zan.

83) A confused lion that was summoned to the nearby area by a wizard is running loose and will attack the players. If they kill it, they will have to deal with the wizard. If they subdue it, the wizard will show up and reward them with a mid-level magic item.

84) A group of 2d8+2 monks is chanting and walking down the middle of the road. If players do not step aside, they will attack.

85) A group of mid-level warriors wants to hire the players as mercenaries for 5 gp a day. They want to attack a local bandit camp and need backup.

86) A priest of Beldaroon is singing as he walks down the middle of the road. He will give the players a potion of cure moderate wounds if they listen to his song.

87) A group of 2d8 soldiers is marching down the road. They are bored and will attack no matter what. If they’re killed, players will have trouble with the local rulers – especially when a tribe of orcs attack.

88) A mad wizard named Texus Tallum has manipulated the nearby animals into attacking people. The animals are carrying diseases that he has created.

89) A group of 2d4+2 goblins are standing on the side of the road. They will tell the players about an abandoned mine nearby filled with giant bats. If the players go there, they will find an underground empire of 2d8+8 giant bats.

90) In the distance, the sound of hooves hitting the road get loader. All of a sudden, a group of 2d8 male and female centaurs gallop up. They will demand food and gold. If they do not get any, they will attack.

91) A group of 2d4+4 barrow wights are standing on the side of the road. If players approach, they will attack and try to possess their bodies.

92) Two vampires that recently fed and are still hungry and ambush the players.

93) Three mercenaries are standing on the side of the road. They are recruiting fighters for a local army. Their names are: Bartholomew, Frederick, and Henry. A tribe of orcs is going to be attacking, and they need help. They’re being paid handsomely.

94) Two ogres (drunk) stumble down the road, yelling and laughing. They will attack anything that gets in their way.

95) A group of 2d8 dwarves are standing around the road. They are not moving. If the players approach, they will attack. The dwarves are standing guard over a nearby dungeon entrance.

96) A man dressed in green is standing on the side of the road. He will offer to sell the players a mid-level magic item for 100 gp. If players ask for a receipt, he will attack.

97) A merchant has set up a temporary shop beside the road. His name is Terrance, and he is selling all sorts of purloined goods.

98) A group of 2d4 jackals is running toward the players. They are followed by 2d10 gnolls who want to kill.

99) A vulture circles overhead.

100) A group of three adventurers is standing on the side of the road. They will ask the players if they have seen a stranger in the area by the name of Clint. Their names are: Jean, Jessica, and Phil. Clint is a sickly looking man with a Ring of Invisibility. Clint has been spotted in the area. They are hunting him to steal the ring. They will try to get the player’s assistance. If the players instead help Clint, he will lead them to an even bigger treasure in a nearby dungeon that they can win.

Even More Random Road Encounters?

Want more random road encounters? Head over to Random Encounters AI. You can also check out my NPC generator – which is also free to use. Finally, I’ve put together a set of over 2 dozen RPG tools you can use at LitRPG Adventures. Members also get access to our growing library of RPG content. We’ve currently got over 25,000 generations in the library, so come check us out!


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Paul Bellow

Paul Bellow

Paul Bellow is a LitRPG author, RPG game developer, and old school webmaster. He's been playing tabletop games since the 1980s. He started Random Tables RPG as a way to give out free D&D and Pathfinder content to the world. Enjoy!