D100 DND Fantasy Roadside Encounters

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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.

Want even more random encounters? Head over to Random Encounters AI today.