100 DND Road Encounters – 5e Compatible

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This is a list of 100 road encounters – 5e D&D compatible, but they can be used for other tabletop RPG systems. I’ve got a free website with even more random road encounters if you need more.

Fantasy RPG Random Tables Books


Make life as a Game Master easier.... If you play Dungeon & Dragons, Pathfinder, or other fantasy tabletop role-playing games, this RPG random tables book is full of encounters, NPCs, and more. Available as an eBook or in a classic print format. Either way, you'll have a wealth of adventure ideas at your fingertips.


  1. Players encounter an old man sitting on the side of the road. He is a philosopher, and he is very strange. He will talk about the nature of Good and Evil for hours. He will not respond to questions or shut up.
  2. Players encounter a group of traveling merchants. They are transporting a large cage full of monkeys. Players can buy the monkeys for 1 copper each. 
  3. Players encounter a group of traveling musicians. They are very good. They are from a distant land and are on their way home. They are willing to join the party for a price. The price is very high. 
  4. Players encounter a group of traveling minstrels. They are very bad. They are on their way to a nearby town to perform. 
  5. Players encounter a group of traveling jugglers. They are very good. They are on their way to a nearby town to perform. 
  6. Players encounter a group of traveling actors. They are very bad. They are on their way to a nearby town to perform. 
  7. Players encounter a group of traveling merchants. They are transporting a large cage full of parrots. Players can buy the parrots for 1 silver each. 
  8. Players encounter a group of traveling merchants. They are transporting a large cage full of ravens. Players can buy the ravens for 1 gold each. 
  9. Players encounter a group of traveling merchants. They are transporting a large cage full of doves. Players can buy the doves for 1 copper each. 
  10. Players encounter a group of traveling merchants. They are transporting a large cage full of crows. Players can buy the crows for 1 bronze each. 
  11. A lone horse is walking on the side of the road. 
  12. A traveling bard is sitting on the side of the road, playing a lute. He looks tired. He will sing about the history of this area and the people who have lived there. He will not mention any evil doings. He will tell you that he was traveling to a local city, but he was robbed by bandits, and he is heading back to the city he came from. 
  13. A man is walking on the side of the road. He is carrying a heavy load on his back. He looks tired and angry. 
  14. A man is walking on the side of the road, carrying a heavy load on his back. He looks tired and happy. 
  15. A man is walking on the side of the road, carrying a heavy load on his back. He looks tired and scared. 
  16. A man and a woman are standing on the side of the road. They are arguing with each other. The woman looks mad, but she is actually scared. The man looks mad, but he is actually sad. They will stop arguing when they see you. 
  17. A woman is sitting on the side of the road, singing a sad song about lost love and lost kingdoms. 
  18. A group of men are sitting around a campfire, drinking and laughing. They will invite you to join them, but they won’t be friendly after they get drunk. 
  19. An old woman is walking down the road, looking for food and shelter. She is carrying a heavy load on her back. She looks tired and mad. 
  20. An old woman is walking down the road, looking for food and shelter. She is carrying a heavy load on her back. She looks tired and sad. 
  21. A group of 3d6+10 human pilgrims from another world are headed to the Tower of the Mad Mage to pay their respects to the late wizard. They are not well armed or well equipped, but they are well fed and will trade food for other supplies. 
  22. The party sees a group of ten men and women wearing robes and carrying staffs. They are chanting a spell, and are trying to conjure a demon. The party can stop them, or let them summon the demon and see what happens. 
  23. A group of four men and women wearing black robes and carrying staffs are approaching from the other direction. They are chanting a spell, and are trying to banish a demon. The party can help them, or let them try on their own. 
  24. A man is sitting on the side of the road, crying. He was walking along, minding his own business, when a group of six kobolds ambushed him. They killed his donkey, stole his possessions, and left him for dead. He is wearing rags and has nothing of value. 
  25. A group of 4d6 humans are heading to the Tower of the Mad Mage to pay their respects to the late wizard. They are not well armed or well equipped, but they are well fed and will trade food for other supplies. 
  26. The party sees a group of seven men and women wearing robes and carrying staffs. They are chanting a spell, and are trying to conjure a demon. The party can stop them, or let them summon the demon and see what happens. 
  27. A group of four men and women wearing black robes and carrying staffs are approaching from the other direction. They are chanting a spell, and are trying to banish a demon. The party can help them, or let them try on their own. 
  28. The party sees an elderly couple sitting on the side of the road. They are holding hands, and have a look of contentment on their faces. As the party approaches, they look up and smile at the party. The woman says, ‘I knew you would come.’ She reaches into her pocket and hands a player a map. It is a map to a nearby dungeon. She says, ‘It’s for you.’ 
  29. The party sees five men and women wearing black robes and carrying staffs. They are chanting a spell, and are trying to banish a demon. They look panicked, as if they need help. The party can help them, or let them try on their own. 
  30. A man is laying on the side of the road, groaning in pain. He was walking along minding his own business when he was attacked by a kobold ambush. He was beaten up pretty bad, but he will be okay if he gets medical attention in time. 
  31. A group of pelgrane are attacking a caravan. They are riding on giant lizards. 
  32. A group of human soldiers are standing guard over a group of prisoners. The prisoners are being held in a jail cell. The jail cell is made of stone and is attached to the side of the mountain. The soldiers are being paid by a wealthy merchant to keep the prisoners inside the jail cell. The merchant’s name is Seddar, and he is a merchant that travels between the city and the nearby fortress. 
  33. A group of human mercenaries are travelling through the mountains. They are travelling to the nearby fortress to join its army. 
  34. A group of 2d6 goblins are hiding in the bushes. They are watching a group of 2d6 humans who are walking along the road. 
  35. A group of 2d6 orcs are attacking a caravan. The orcs are wearing dark armor and riding dark steeds. 
  36. A group of 1d4+2 goblins are hiding in the bushes near the road. They are hiding near a stream. The goblins are hunting for fish to eat. 
  37. A group of humans is standing guard over a group of villagers who are working on a bridge over a fast-moving stream. The humans are being paid by one of the villagers to protect them from attacks by the goblins and their giant lizards. 
  38. A group of humans is standing guard over a group of villagers who are working on a bridge over a fast-moving stream. The humans are being paid by one of the villagers to protect them from attacks by an evil wizard who lives in a nearby tower. 
  39. A group of humans is standing guard over a group of villagers who are working on a bridge over a fast-moving stream. The humans are being paid by one of the villagers to protect them from attacks by a nearby dragon and its wyverns. 
  40. An old woman is sitting on her porch, watching the players as they pass by her home. She asks the players if they have seen her lost pony. She has not lost a pony. She sells extremely rare weapons to the highest bidder, but only if they appear to be good people. 
  41. The Players are approached by a man named Sebastian. He is a clown and he wants to join the party. 
  42. The party sees a man wearing a tattered cloak. He is walking down the road. He looks very nervous. He looks around, then approaches the party. 
  43. A local bard is walking through the woods. The party sees him. He is playing his lute and singing. 
  44. A group of 2d6 men are walking down the road. They are all wearing gray tunics and brown pants. They are all armed with short swords, short bows, and daggers. They are a group of mercenaries. 
  45. A group of 2d6 men are walking down the road. They are all wearing gray tunics and brown pants. They are all armed with short swords, short bows, and daggers. They are a group of thugs and they are looking for someone to mug, but they don’t see anyone on the road… 
  46. The players see two men wearing black tunics and black pants. They are walking down the road towards them. 
  47. A man named Henry Henry is walking along the road towards the players. He is wearing a black cloak with a hood, and he has a walking stick in one hand and a lantern in the other hand. He is an elderly man, but he is not frail. He says that he is looking for someone to give him passage to the next village, but he wants to get there as quickly as possible because he has urgent business there… 
  48. The players see 2d6 men wearing colorful tunics and colorful pants, each one wearing a short sword, short bow and carrying a dagger in their belt. They are a group of minstrels returning from a performance at the castle of Lord Dragoon at the River of Dreams… 
  49. The players see 2d6 women wearing colorful dresses and colorful petticoats, each one wearing a short sword and carrying a dagger in their belt. They are a group of ladies in waiting returning from a performance at the castle of Lord Dragoon at the River of Dreams… 
  50. The players see a man wearing a black cloak and he has a hood which covers his face. He is walking down the road towards them and he has a walking stick in one hand and a lantern in the other hand… 
  51. You see a funeral procession. They are carrying the body of the man who died. He was an elderly man who was killed by his son, who is being led by the funeral procession. A nearby town has said that he will be allowed to live and start a new life there. 
  52. A group of merchants with a group of dog pull wagons are heading to another city to trade with another group of merchants. The dogs are not well fed and are not friendly. The merchants seem suspicious and may be intending to rob the players. 
  53. You see a travelling theatre group. They are doing a play about a group of people who travel to a distant land and learn about their ancestors and return home wiser for their travels. It is only one act and it is mediocre at best, but the players will be entertained. 
  54. You see a small village with a small wall around it. A large stone block with a large sword sticking out of it is in the middle of the village. The sword is made of bronze and is twenty feet tall. A famous hero died here and they have decided to make his tomb a tourist attraction. It’s odd, but it gets people to come to the village and spend money there. 
  55. An old, clearly abused woman is sitting on the side of the road with an old dog looking for food. The players can try to help her or ignore her. She is actually a powerful witch who is testing the players’ character. 
  56. Fantasy RPG Random Tables Books


    Make life as a Game Master easier.... If you play Dungeon & Dragons, Pathfinder, or other fantasy tabletop role-playing games, this RPG random tables book is full of encounters, NPCs, and more. I also have a complete adventure, including a dungeon map and room descriptions. Check out the Dungeon Maps Described or Random Encounters series today!

  57. You see a group of men riding horses and wearing armor heading towards the players. They are wearing chainmail and carrying swords and lances. The men are from a nearby area that has been raided by a nearby orc tribe. They are looking for help fighting the orcs as they have stolen their horses and stolen their sheep and killed their children. 
  58. A group of men are carrying a large wooden box on their shoulders towards the next town. They seem tense and are looking around nervously as they travel along the road. They are carrying a large amount of money that was collected for the king’s taxes and it was stolen by thieves. They are taking it to the king to be returned to the people. 
  59. You see a man wearing ragged clothing sitting along the side of the road, holding a sign that says ‘Need work.’ He has been traveling for a long time and would like work doing something. He is an excellent farmer and will work for cheap if players offer him work in their own fields. He doesn’t want any handouts simply work for his board in exchange for his labour. 
  60. A druid named Seanor is walking along the road towards the next village carrying a staff made of oak wood with a crystal on the top of it that pulses with an odd light every now and then when he walks along the road. His hair is long and tangled with leaves and twigs sticking out of it here and there, his clothes look like they have been worn for years and his boots have holes in them and his toes stick out of them when he walks along the road. He looks like he has been traveling for hours, possibly days judging by how tired he looks. 
  61. A group of men wearing chainmail riding on horses with lances and swords are riding towards the players 
  62. A group of 2d6 goblins is attacking a wagon. If the players help the wagon, the wagon driver will give them a free ride. 
  63. A group of 2d6 bandits is attacking a merchant caravan. If the players help the merchant caravan, they will receive a reward, depending on what the merchant is carrying. 
  64. A group of 2d6 ogres is attacking a merchant caravan. If the players help the merchant caravan, they will receive a reward, depending on what the merchant is carrying. 
  65. A group of 2d6 orcs is attacking a merchant caravan. If the players help the merchant caravan, they will receive a reward, depending on what the merchant is carrying. 
  66. Two men are arguing about where to bury a third man who has just died of a fatal disease. They will not let anyone else near the body – not even priests or healers – because it carries such a terrible disease that anyone within five feet of the body will die and become a zombie within minutes. 
  67. The players encounter a man who is stuck in quicksand. He is sinking quickly and will die if he is not rescued! 
  68. The players encounter a man who has been robbed by bandits and left for dead on the road. He has been badly beaten and left to die on the road. He will die if not rescued. 
  69. The players encounter a man who has been attacked by a pack of wolves that has mauled him terribly, leaving him for dead on the road. He will die if not rescued quickly. 
  70. The players encounter a man who has been attacked by a pack of wolves that has mauled him terribly, leaving him for dead on the road. He will die if not rescued quickly. He has a pouch containing 100 gold pieces that he was bringing to a nearby village to pay for some goods. If he dies, it will be lost forever. 
  71. A priest of Good is ranting and raving about how evil people should be punished for their crimes and about how the world would be better off without them. He is clearly insane and should probably be put down like a rabid dog. 
  72. A man is riding a donkey. If the party approaches, he will say, ‘Don’t be fooled by appearances. I’m not a man. I’m a mule.’ If they talk to him, he will tell them that he is a wizard and his donkey is his familiar. 
  73. A group of children are playing. If the party approaches, they will run away. They are actually thieves, and they are hiding in the bushes, waiting for a mark to walk by. 
  74. A group of children are playing. If the party approaches, they will run away. They are actually thieves, and they are hiding in the bushes, waiting for a mark to walk by. They are dressed as animal and are trying to scare people away so they can steal their stuff. 
  75. The party sees a small house with a sign that says ‘Johnson’s Boarding House’. The house looks abandoned. Inside, you see a man sitting in the corner of the room, crying. He’s wearing expensive clothing, but he’s beaten and broken. The MC will not allow the players to ask him what happened here or try to help him. He’s just a random NPC, and all you can tell about him is that his name is Carl Johnson. 
  76. The party sees three small gray wolves in the middle of the road, howling at the moon. If they approach, they will attack. 
  77. The party sees two small gray wolves in the middle of the road, howling at the moon. They are actually werewolves in wolf form, and they will attack if they sense that anyone has sympathetic magic (healing magic, bard music, etc.). 
  78. A man wearing a red robe is walking down the road. If the party approaches, he will stop and say, ‘Do not disturb me or I will cast a spell on you!’ The man is actually a local wizard studying new spells, and he does not want anyone to disturb him while he concentrates on learning new spells. 
  79. A town crier is walking down the road in front of you, yelling out news about the missing nobles and the reward for finding them. People pay closer attention to the town crier than they do to you because the town crier is an important public figure who is trusted by the public because of his position as a trusted public servant while you are just some random strangers no one has ever seen before so no one trusts you yet even though you’re also trying to help find the nobles and bring them home safely too. 
  80. A group of women are walking down the road, talking about how beautiful their dresses are and how much attention they’re getting from men and how much fun it is to flirt with men and how much money they’re going to make from all the rich men who will try to buy them dinner and buy them gifts just so they can touch their pretty dresses and feel good about themselves for a little while because everyone loves feeling good! 
  81. The party sees a group of women in long dresses walking down the road, talking about how beautiful their dresses are and how much attention they’re getting from men and how much fun it is to flirt with men and how much money they’re going to make from all the rich men who will try to buy them dinner and buy them gifts just so they can touch their pretty dresses and feel good about themselves for a little while because everyone knows feeling good about yourself is worth more than money because money can’t buy you love but love can sure as hell buy you money! 
  82. The party encounters a merchant caravan from another land. The merchants are friendly and willing to sell the party all the supplies they need and more. 
  83. The party comes across a man named Henry and his two sons, Michael and Thomas. Henry is a farmer who was attacked by a pack of wolves while he was out in the fields tending to his crops. Henry’s sons were killed by the wolves, but Henry was able to escape from them. 
  84. The party comes across a man named Alfred who is standing by the side of the road looking lost. Alfred says he is looking for his uncle’s farm. Alfred is not sure exactly where it is, but he is sure it’s somewhere nearby. 
  85. The party comes across a farmer who has been attacked by a pack of wolves. The farmer has been badly injured and will likely die if he does not get help soon. 
  86. A group of men on horses approaches from the distance and approach the party. The men are carrying swords and shields, and they look like they are ready for a fight. 
  87. A group of men on horses approaches from the distance and approach the party. The men are wearing robes and carrying staffs that look like they are made of wood. The men look like they are Mages or Priests, and they do not look friendly. 
  88. A farmer named Henry approaches the party and offers to sell them some vegetables from his farm. Henry has several carts filled with vegetables that he is selling to other nearby villages and towns. Henry has several horses and several wagons full of vegetables, and the party can buy anything they want from Henry’s stock of vegetables. 
  89. A group of men on horses approaches from the distance and approach the party. The men are carrying swords and shields, and they look like they are ready for a fight. 
  90. The party comes across a man named Alfred who is standing by the side of the road looking lost. Alfred says he is looking for his uncle’s farm. Alfred is not sure exactly where it is, but he is sure it’s somewhere nearby. 
  91. A group of men on horses approaches from the distance and approach the party. They are mages who will attack when the time is right. 
  92. The party see a caravan of ox-carts carrying sacks of grain and crates of chickens. The caravan is being escorted by 2d6 guards on horseback. The guards are wearing chainmail and carrying spears. The leader of the caravan is a tall man with a white beard and a staff. He will introduce himself as a priest of Pelor. He will offer the party food and drink. He will ask them to protect the caravan. If asked, he will say that he is transporting grain to the city. 
  93. The party see a group of men wearing blue robes and carrying scrolls, books, and writing implements. The men are arguing about whether or not the sky is blue or green. 
  94. The party see a group of men wearing brown robes and carrying a coffin on their shoulders. The men are singing funeral songs as they walk down the road. 
  95. A group of men in black robes approach the party and ask for directions to a nearby town. If the party refuses to help, the men will attack them with magic. The men are cultists of Vecna. 
  96. Fantasy RPG Random Tables Books


    Make life as a Game Master easier.... If you play Dungeon & Dragons, Pathfinder, or other fantasy tabletop role-playing games, this RPG random tables book is full of encounters, NPCs, and more. I also have a complete adventure, including a dungeon map and room descriptions. Check out the Dungeon Maps Described or Random Encounters series today!

  97. A group of women wearing red dresses are collecting money from people walking down the road. If asked, they will say that they are raising money for the poor. They will not attack unless attacked first or if they feel threatened. 
  98. A man carrying a sack of flour stumbles into the middle of the road and collapses. He is unconscious and has been robbed of his money and valuables. A nearby sign reads ‘Beware of thieves.’ 
  99. A man wearing black robes and carrying a staff approaches the party and asks for directions to a nearby city. He will ask for directions in Basic and then again in another language the party does not understand. He will then attack them with magic if he does not receive the directions he wants or if he feels threatened in any way. 
  100. The party sees a group of women wearing robes and carrying staffs. They are chanting as they walk down the road. They will not stop for anyone or talk to anyone. 
  101. A group of men wearing robes and carrying staffs are walking down the road and talking about wizards, magic, and monsters.   
  102. A man wearing a bright red robe attracts the party’s attention by shouting at them. He is selling magic items. 
Road Encounters 5e DND
Road Encounters 5e DND


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