D100 Random Wilderness Encounters for D&D 5e

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I’ve got a great list of 100 random wilderness encounters for D&D 5e – and other fantasy tabletop systems (Pathfinder, GURPs, MERP, you name it!) In all seriousness, if you like these, you can check out more D&D random encounters at my other website. Check out these examples first to see what you’re going to be getting. While not perfect, it’s a great launching pad for ideas as a DM. Let’s get started.

1) You see a male half orc on a horse leading a herd of sheep. He is wearing a big cowboy hat, cowboy boots, dancing a jig, and singing (and badly). His name is Hank, and he’s a bard.

2) Up ahead, a clearing opens up and in the middle of it, is a huge campfire. The ground around the fire has been carefully cleared of any sticks or twigs, and an enormous bedroll is laid out in front, with various dried meats and cheeses hanging from trees. The fire crackles and pops. Standing by the fire, you see a female half elf. She is tall, wears chain mail, and her eyes are blue. She is roasting a squirrel on a spit. Her name is Sally and she’s a ranger.

3) You come up to a small house made of wood. Smoke rises from the chimney, and you hear cheerful singing. You knock on the door, and a male human with a brown beard and leather apron opens the door. He is holding two swords and is muttering something about elves as he stomps out the door. He is an NPC, and his name is Murphy.

4) The trail goes through a narrow gap in between two rocky outcroppings. In the gap, you see a stalagmite set into the ground. A small creature, a male halfling, climbs down the stalagmite. He is wearing a fur vest, leather pants, and leather boots. He has a small axe and is chuckling to himself. His name is Snargle, and he’s a druid.

5) The trees start thinning out, and up ahead you see a clearing. A tall, skinny tree grows in the center of the clearing. A short, fat woman sits in the tree. Her legs dangle down the side. She is drinking a skin of something and humming to herself. Her name is Greta, and she’s a ranger.

6) A small, one room cabin made of wood appears up ahead. A tall man with a big build walks in and out, carrying an assortment of items, including a wood table, chairs, and some food. Soon, the cabin is furnished and the man takes a seat at a table and starts eating. His name is Grog and he’s a cleric.

7) You see an old man in the middle of the trail, dirty and cracked. You see a small, lonely house behind him. The man is yelling, but you can’t hear him. The house is empty, but there’s a warm fire up in the fireplace. This is a male human ranger, and his name is Bart.

8) A large, orange and black striped cat is sleeping in a pile of bones. It lazily opens one eye as you approach and then closes it again. This is an animal encounter, and it’s up to the DM to decide what kind of animal it is. The tabaxi is named Roll, and he’s a mid-level ranger.

9) The trail opens up into a wide, deep canyon. A rope bridge spans the canyon. On the opposite side, a tall, thin man stands with a smile on his face and an axe hanging at his waist. He introduces himself as the bridge toll keeper and asks for 10 gold. When the characters continue to the next encounter, you can have the man there again next time. It takes the 5th level party nearly an hour to cross the canyon because the rope bridge is old and sturdy. If the party doesn’t have 10 gold, it’s a DC 15 athletics check to cross the bridge.

10) The characters come upon a treasure chest and find a note on top. “My, my, my. What’s this? An honest man? You have found my treasure. I have one rule: no pick-pocketing. Please, enjoy your stay in the town of Fin City. If you are here to pick my pocket, you should first go to the bar, Ringo’s Inn. I’ll be watching you, so don’t try anything funny.” The chest is a mimic who is looking for its owner.

11) A small, unmapped staircase leads up to a small, wooden shack. Inside, the air is humid, and plants and small, green orchids are growing on the walls. A sage is sitting in the middle of the room. He can answer any three questions. After this encounter, the staircase disappears.

12) A blacksmith is forging a sword in his open-air shop. The walls of the shop are completely white-hot from the fire he’s working with, and the sword is almost finished. He doesn’t speak, but in his eyes you can see that he does not appreciate visitors. Once he’s finished the sword, he gives it to the party.

13) A thin woman with the face of a gazelle is preparing some food by a small fire in her small, stone home. She offers the party food and drink. She’s a loner and doesn’t ask for much. She’s simple, though she is powerful for a druid. If the characters accept, she’ll tell a story about a dragon that used to fly over her home. As she’s telling the story, the players see an immense shadow flying above the house. She tells them to be on their way, and she will give them a piece of advice: never get into a staring contest with a dragon.

14) It’s raining heavily, and the characters hear a boy’s cry. They look around a corner and see a boy being held up by two orcs. One orc is holding an axe, and the other orc has a large sack. The orc with the sack looks at the party and shouts, “Come on, stop staring at us! If you’re nice, we might share our gold with you!”

15) The party meets an elderly man with a bad back on the side of the road. He says he’s been fending off some goblins, and he is walking toward the next village. He can’t make it on his own, so he asks the party to escort him. If the party accepts, he will follow. He complains of difficulty walking and constantly needs to rest. On the third day, he suddenly vanishes, and the party hears a voice whisper: “You’ll never walk again!”

16) A group of adventurers are camping for the night. They are in a circle, and a fire burns in the middle. It’s a band of five adventurers on their way to the next town. One of the adventurers is taking the first watch. He’s a tall, dark-skinned human with a scar across his face. The party can approach him and ask for directions if they’d like. When the watch ends, he says “Good morning, how did you sleep?” and continues walking.

17) A farmer is staring at the party, and he says, “There’s something you need to know. It’s the shadow! I’ve seen it, but no one believes me! We need to get together and talk about this. The party can approach him at any time before finishing the quest.

18) Two goblins are arguing in a cave. The argument is about which direction to go to find a larger party of goblins. One says south, and the other says north. They are about to fight, when a goblin hiding in a corner says, “I know where the others are! I overheard them talking last night. We should go west!”

19) An orc is walking down a trail. He’s seen the party, but he continues to walk. He comes to the next turn in the road and turns around. He walks back to the party, and he says, “This is where I got lost last time!” (This is your chance to roleplay!) He asks if this is the right way, and he will follow the party if they say yes. When night falls, he will sneak off into the woods and run away.

20) A man is standing on the side of a road. He’s holding a baby, and he says, “I’m not sure if you are the ones I want to speak to, but the lord of the castle told me to wait here. He said you’d be passing by, and you’d be more likely to speak to me than him. He says you’re looking for a missing child. I know where to find him. He’s in the village, locked under the floorboards. I found him! He’s been there for years! I was a servant in the castle, and I was taking a nap. He’s been trapped under there for a decade! This? Oh, it’s another baby. Don’t worry about it.”

21) A fat man slumps over. He’s dead. If the party searches the body, they will find a letter that says, “I have your gold. If you want it back, come to the cave on the side of the mountain. My bandits and I have already gone to the village to buy supplies. If you don’t show up, your corpse will be a long time in the ground.”

22) A man carrying a pack is walking down a dirt road. He’s cold, and he’s looking for shelter. If the party offers him shelter in their camp, he will approach the camp. He will tell the party that he is from the next city over. He has a job offer, but he lost his way, and he will ask for directions. He can’t recall the name of the next city, so he asks for a description of it. Make something up, and he’ll say “Oh, right. I know where that is.” He tells the party he’ll stay with the party overnight, and he’ll get up early to continue on his way.

23) The party hears a woman shouting, “I don’t know where we are! Tell me, or I’ll kill you both! Wait, I can kill you with my magic, so I don’t need to know! You’re just hurting me more by lying to me! If you don’t tell me where we are, I’m going to kill you both! No, I don’t know where we are, I swear! We were driving, and the road just disappeared! I’m telling the truth!”

24) A dragon turtle and three ogres are arguing. The ogres say they won’t go till the dragon turtle goes first, and the dragon turtle says he isn’t going into the cave until the ogres go first. The ogres are saying the dragon turtle will eat them, and the dragon turtle is saying the ogres are stupid. They argue for a long time, and the party overhears them.

25) The party hears a woman singing. She’s walking down a dirt road, and she’s singing “I’ll Take You Home Again, Kathleen.”

26) A riderless horse has escaped from the nearby town. The party sees it running, and they chase after it. The horse runs through the woods, and the party follows it. They will eventually catch the horse and lead it back to town.

27) The party hears a voice screaming. It’s a fae voice. A fairy says, “Shush! I’m trying to speak with them!”

28) The party hears a woman singing. She’s walking down a dirt road, and she’s singing, “Bibbidi-Bobbidi-Boo, anyone can cook.” She’s a drunk half-elf named Rhondasia.

29) A hunter has fallen asleep in a tree. The party looks up and sees a human in a tree. They approach him and ask if he’s seen any bandits. He says no, and he was sleeping because he was hunting prey all night. He says he’s been hunting for a long time, and he can’t find any animals for miles. He asks the party if they’ve seen any animals.

30) The party sees a man practicing archery. He’s standing in the middle of a field, and he’s shooting at a target. He’ll say “I’m practicing archery. I’m trying to get better at it.”

31) The party hears a woman singing. She’s walking down a dirt road, and she’s singing, “O, do not tell the priest, let not thy vision be confide in me.” The woman is a witch named Yvaine.

32) There’s a wild wood elf adolescent chasing chickens. He says, “Catch the chicken!” The party can try to catch the animals for him. If they catch them, he’ll give them a reward.

33) The party sees two people fighting with a large snake. The snake is wrapped around their arms. They are trying to free themselves. If the party saves them, the man and woman will be eternally thankful and offer to help the party with knowledge about the surrounding area – including how to avoid snakes … most of the time!

34) A group of four bandits are playing knucklebones, and they want to play the party. The bandit leader is a mid-level assassin who was sent into the wilderness to attack the party.

35) Up ahead, the sound of a horse galloping can be heard. You can hear him coming around the bend ahead. He’s running at full speed. He comes running around the bend, and he looks terrified. He stops for a second and frees a bag from his saddle . . . and you see a flash of blue and a flurry of movement. He takes off again.

36) In the distance, a large bird is trying to take off from a field. He’s flying straight into the air, but he keeps falling back to the ground. He tries to take off a few more times, but he keeps falling back down.

37) The party sees a small cottage on the side of the road. It’s an abandoned home. If the party enters, they’ll find that the cottage is abandoned.

38) The party hears the sounds of a remote wilderness tavern. When they go there, they see a bartender named Butterfoot Buttercup. He’s a mid-level halfling who is on the run from the law for some sketchy magic mishap. He’s a good guy, though.

39) Two bandits on horseback are attacking a merchant. They’ve already killed his guards. His horse is carrying a trade wagon full of goods. One of the bandits rides up to the merchant, and he tries to take the wagon off the merchant’s horse. The merchant says, “Get away from me! I’ll never let you take my wagon!” Then, the bandit punches the merchant in the face.

40) A drunk halfling walks up to the party and asks what they’re doing. He says, “I think you’re doing a great job. I’m proud of you!” He then scurries away.

41) Two humans are bickering. They are in the middle of a field, and they are arguing over the ownership of a cow. One of the humans says, “How are we going to divide this cow?” The other says, “We’ll take it to the town square and let the town decide.” The other one says, “We’re doing this right! If someone wants a part of the cow, they can take it and go wherever they want with it.”

42) An old couple is walking down the country road, and each of them is carrying a large basket full of plants. The two are walking and laughing together.

43) Overhead, you see a dragon fly across the sky. He’s flying towards the mountain range and away from the party. You’re far away from the dragon, but you can hear a dragon roaring in the distance.

44) A man is driving a cart pulled by a camel. He rides slowly down the road, and he’s selling wool socks at every town he passes.

45) A man is playing the lute in the middle of the road. He’s singing a song. A sign near him says, “This is my only source of income. Please give generously!” He’s actually a bandit. A group of 2d10 other bandits are nearby, waiting for an opportune moment.

46) A half-orc is arguing for her life. She’s in chains, and she’s standing at a crossroads. She’s surrounded by 20 soldiers. The half-orc says to the soldiers, “Please, let me live. I’m sorry for what I’ve done. I didn’t mean to break the law. Please, let me go.”

47) An old man is in a field of tall grass. He’s standing in about waist-high grass. He’s staring up at the sky with a look of wonderment on his face.

48) A human is in a field and he’s digging a hole in the ground with a shovel. He’s digging the hole in the shape of a skull. His name is Captain Skullface, and he went insane after the last big war in the land. He’s been digging this same hole for the last 10 years.

49) A woman is yelling at two men in armor. She says, “Please, don’t hurt me! I didn’t do anything! I just live here!” The woman is crying.

50) A dragon is flying towards the mountain range. He’s 80 feet in the air. He’s diving straight towards the ground and turning into a humanoid while he’s at it. Mid-way down to the ground, he changes back into a dragon. He’s a wind dragon. He’s a high level scout from the Dragon Queen. He is flying fast and looking for the party.

51) A young elf is playing in the woods. She is running between the trees and ducking under low-hanging branches. She’s wearing a green dress. The dress is fancy. It looks like it’s made of silk. She’s an illusion cast by a gang of gnomes nearby up to mischief.

52) A drunk dwarf sits in the middle of the road. He’s wearing a fancy purple vest, and he’s really dirty. He has a jug of ale next to him. He’s singing a song. A sign near him says “Drunk Dwarf.” Another dwarf runs up to him and says, “Man, you’re getting really drunk. You should probably head home.”

53) An owl is sitting on the branch of a tree. He’s staring down at the ground, and he’s looking for food.

54) A human man is sitting on the ground. He wears dark, hooded robes. He’s a necromancer. He’s trying to bring his undead army back to life.

55) A wolf is running through the field. He’s chasing after a deer.

56) A group of goblins is traveling in the forest. They’re carrying a chest between them. They’re walking at a very quick pace.

57) A group of goblins are riding giant rabbits through the forest. They’re riding through at a very quick pace. They’re going to get to the edge of the forest around midnight.

58) A group of adventurers is traveling through the forest. They’re traveling in a very well-kept line. Their leader is in the front. They carry long spears with them. They look like a military unit.

59) A group of adventurers is traveling through the forest. All of them are holding sticks with marshmallow on the end. They’re roasting the marshmallows. The smell of the marshmallows fills the forest.

60) Thirteen elves are playing in a meadow. They’re doing tai chi.

61) A woman is sitting on a log playing a dulcimer. She’s playing a sad song. People are gathering around her, and she’s singing.

62) Two old men emerge from the woods. Both of them are really dirty. They’re bandits who got lost ten years earlier. They’re carrying bundles of sticks on their shoulders.

63) A group of dwarves is trying to navigate a forest. They’re doing it in the dark. They’re trying to find their way back to their ancestral home in the mountains.

64) A group of adventurers is walking through a forest. They’re deciding what to do with a giant gem they found in the mines. They had to pay a lot of money to get the gem out of the mine. They’re trying to decide if they should keep it or sell it.

65) Up ahead, a roar can be heard. The party hears the sound of trees being knocked down. Something big is headed towards them.

66) A group of soldiers are chasing a satyr through the forest. They just want to bring him back to their encampment alive. He’s their prisoner. The soldiers are tired and hungry. The satyr is holding a golden chalice. They don’t know why he has it or what he’s doing with it.

67) A party of adventurers are returning to their village with a wagon full of supplies. They’re on your side in the war. They want to get back to their village before nightfall. They’re worried that a bunch of orcs that live in a nearby cemetery will awake and attack them.

68) A druid is tracking a deer through the forest. He’s almost found it, but then the deer slips away.

69) A group of lizardfolk scouts have set up a camp in the woods. Their chieftain has sent them out to find a group of goblins that passed nearby three days earlier. They’re waiting for the goblins to return. They’re going to ambush them. If the goblins approach their camp, the lizardfolk will alert their chieftain.

70) A group of pilgrims are trekking through the forest. They have a small cart. They are traveling from town to town and selling religious trinkets. They have a large wooden cross with them. They’re hoping to sell it to a large church in a nearby town.

71) A small elven village is completely hidden in the forest. There are a few dozen buildings made of wood. Thatched roofs. The postman is delivering mail to the town’s zip code.

72) A forest tribe of wildlings lives in a nearby forest. They’re hunters and gatherers. At night, they move from one campsite to the next. They are afraid of humans, because one day, a group of humans attacked them. All of the wildlings learned how to speak common, because they had to beg for help. They need food and medicine, but they’re afraid to approach a village, in case the humans return.

73) A nearby campsite / outpost is celebrating its founding anniversary. It’s the biggest holiday of the year. A big festival will be held at noon. A bunch of people are washing their clothes by the river. The innkeeper has agreed to hire a few people at the tavern who want some work.

74) A group of deer are grazing in the forest. They’re looking for orchids.

75) Six elves are walking out of the woods in single file. Each of them is carrying a small box. They’re delivering merchandise to a nearby town. They have no money and have to barter for everything.

76) A farmer is trying to repair his wagon. He’s out of rope. He’s tied a few logs together, but that won’t hold his wagon together for more than a few more days. He’s hoping to find rope in the forest.

77) An orc war party is doing battle training. They’re practicing spearing at a target.

78) A group of goblins is riding wolves. The wolves are vicious. The goblins are trying to find a village to plunder.

79) A group of rangers is trying to find a deer they shot. They want to make sure they didn’t hit anything.

80) A group of elves is hunting deer. They’re using a spear launcher to kill deer that would otherwise be too far away.

81) A group of orcs is trying to get a sheep off of a cliff. They think it fell off. They don’t know it’s their sheep.

82) A group of goblins is trying to fix their cart. Something broke, and they’re trying to fix it.

83) A group of dwarves is cutting down trees. They have a set of massive chainsaws. They’re working on cutting down a massive tree.

84) A tribe of human barbarians is having a funeral for a friend. They’re burying him with all of his possessions including his car.

85) A merchant is trying to hire an elf to deliver a message to his friend. He’s offering a lot of money, but his friend lives on the other side of the forest.

86) A barbarian is trying to make his way back to the barbarian camp following his latest raid. He’s lost and exhausted.

87) A dwarf is trying to get a deer off of a cliff. A goblin is trying to get a sheep off of a cliff. They’re trying to help each other.

88) A band of goblins is looking for a village to attack. They’ve been traveling for weeks. They’re exhausted.

89) A group of elves is following a trail of blood. They’re hunting a wounded deer. It’s their only source of meat.

90) A group of orcs is moving logs through the forest. They’re moving them for their village.

91) A group of elves is hunting a deer. They’re tracking a deer. They’ve been tracking him for days.

92) A group of humans is looking for a lost friend. He’s got a map, but he got lost.

93) A group of humans is cooking on a bonfire. They’ve got a deer roasting. An old woman is teaching them how to cook it.

94) A human hunter is tracking a bear. He crashed her and he needs to take her head.

95) A group of orcs is moving logs. They’re trying to get them to their village.

96) A group of elves is hunting a giant deer. They’re trying to bring it back to the village. The village is starving.

97) A group of elves are following a trail of blood. They’re tracking a bear. They think it’s wounded.

98) A group of humans is picking berries. They’re camping with a druid and a bear. They know that something is watching them.

99) A group of humans is caught in a storm. They’re camped by a lake. They’re trying to stay warm.

100) A group of humans is hunting. They’re trying to track and kill a deer. They’ve been tracking it for days.

Final Thoughts

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