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100 Dungeons and Dragons Roadside Encounters

Travel in d&d or pathfinder doesn't need to be boring..

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Travel time in Dungeons and Dragons can be boring. But it doesn’t have to be. Lord of the Rings taught us that the adventure is in the journey. Here are 100 Dungeons and Dragons roadside encounters to make that trip to the next town a little more enjoyable.

You’ll note that few of these lead immediately to “roll initiative.” Instead, these are meant to add intrigue, introduce an important NPC, or perhaps serve as a red herring. And, you know, some will lead to the words “roll initiative,” so that’s nice.

You can read through them to work as inspiration for encounters you want to spring at your players, our you can roll 2d10 and take your campaign off the rails by letting chance dictate. Regardless, enjoy.

1. A huge nest has fallen from a tree on the side of the road. The strange-looking eggs within seem on the verge of hatching.

2. A dwarf falls from the sky onto the road with a splat. (Did a creature drop it, was he launched into the air, did he fall from a floating fortress?)

3. A row of severed heads on spikes and a warning sign claiming, “Dis Rode Belong Negan”

4. A very small goblin wearing an old carpet as a cape leaps into the path and demands tribute.

5. A crazed halfling, starved out of his mind, jumps to the backs of the PCs and rips their packs apart with his teeth in search of food.

6. A bounty hunter tracks his target.

7. A lush garden is filled with ripe vegetables. It is protected by a magical ward, but what is triggered when entering the garden?

8. A monstrous mount is ridden by a gnome. Friend or foe?

9. Two guards hold a wanted poster. They carefully studies the party as they pass by.

10. A smiling roadside merchant roasts rats, frogs, and squirrels on sticks. He offers a bite to the PCs.

11. A chatty bard walks alongside the party. Time for an exposition dump!

12. A bridle ties a well-groomed speckled horse to a nearby tree. The horse is fitted with an elegant but empty saddle. Who does it belong to? Do the PCs take it?

13. A powerful storm forced you to take the only available refuge: an elderly couple’s home just off the side of the road. The two room home holds numerous open cups of the same pungent liquid.

14. A naked bard asks for a lift to the nearest inn where he left his clothes and money.

15. Alongside the road, a charlatan asks the party if they want to see a performance of his trained pets. The slightest affirmative answer causes Steve to give a whistle, and a huge swarm of ravenous locusts suddenly manifests.

16. A fat friar hurries past the PCs mumbling, “It isn’t fair.”

17. An evil wizard is tied to a stake, the body still smoking.

18. Three young men work on tipping over an occupied outhouse.

19. A band of orcs runs toward the party. They look over their shoulders and try to run through the party. Something dreadful has terrified them, and the party is heading in its direction!

20. Traveling off the main road, the PCs feel like they are being followed. Who is hunting them?

21. Three types of meat hang on a spit over a campfire. It is clear that it is three types of humanoids that hang over the flames.

22. A snowy road hides a sinkhole that chutes the party on a slalom slide down the mountainside.

23. A well-spoken bugbear wearing fine studded leather armor is trapped under a fallen tree. He begs the party to come to his aid.

24. A ranger stops by the group’s camp one night and gives them advice on the trail ahead, including places to camp and a tavern where they can get good rates if they mention his name. All his advice is impeccable, but when they mention his name at the tavern, they’re told he died years ago on that very road.

25. A shopping list for potions lies on the ground.

26. The local baron has enacted a toll bridge. Several peasants were unaware, and cannot afford the toll. They beg the PCs for change.

27. You find the remains of a pouch that contains coins fro ma land you do not recognize.

28. The party hears a long stream of curses further up the road. Then they spot a head in the road. A person is still alive, buried up to his neck!

29. An arrow hits a nearby trunk, a message wrapped around the shaft.

30. A bridge is missing. Where it used to be is now a ferry service, for a sizable fee. The ferry looks like it might consist of bridge parts, and only takes a few travelers at a time.

31. A loaded wagon travels down the road toward the party, but it has no apparent means of propulsion.

32. As bandits attack, the PCs realize a friend of theirs is among the robbers.

33. There is a mysterious flicker ahead, and one member of your party suddenly stops, paralyzed.

34. Orcs gather twigs and berries along the road and it’s clear they have non-hostile purpose. Will the PCs attack just because they are orcs?

35. A tree falls onto the road. Then a fireball blows up the tree. It appears the PCs are in the middle of a skirmish between druids and fire wizards.

36. Flowers by the roadside turn their heads to follow the party, and they’re getting larger.

37. An overturned beer cart lies in the road. Nearby, an enormous troll snores loudly, surrounded by empty kegs.

38. A set of shackles lies at the side of the road.

39. A village can be seen to the west. It isn’t on any of the maps.

40. Three pilgrims trudge along the dusty road, an old man and two young men. Simple travelers? Or are they more than they seem?

41. You stumble upon an old scroll case wedged between a tangle of tree branches. Inside is a village’s charter of rights and freedoms.

42. A dead magic user clutches a scroll in his stiff hand. The scroll says something important.

43. A single giant footprint lies along the path. There are no other signs of such footprints in the area.

44. You party awakens to find all your gear has been stolen during the night. A quick search reveals twelve sets of tracks and, lying in the middle of your campsite, a smoldering pouch of herbs that, when you sniff them, make you feel slightly drowsy.

45. An enormous dragon lands on the road in front of the group. It asks for directions to a certain village, gives the party a generous tip, and then flies off saying he intends to raze it to the ground.

46. An exotic, almost alien weapon or tool lies on the side of the road.

47. The PCs mysteriously repeat a piece of road they already passed, though the route has been perfectly straight to this point. The road even includes their footprints.

48. A dozen townsfolk are running after a fleeing woman and attempting to stone her to death for being a prostitute.

49. Two other adventuring groups are arguing in the middle of the road.

50. You see a man-sized shadow from the left side of the road waving its arms at you. “Over here, quickly, I’ve caught one!”

51. A person fleeing arranged marriage seeks refuge with the PCs.

52. Picked mushrooms lay on stump to dry.

53. A strange old man offers the PCs a scroll in a language they cannot read.

54. Gnomes are holding a yard sale! They have any number of strange and fascinating contraptions.

55. Someone has scattered caltrops across the road.

56. You encounter a monk, a monkey, a turtle and a pig, all heading west.

57. A weathered sign points off the road, yet with no apparent trail to follow.

58. The next 100 feet of road are covered with newly grown grass.

59. Ladies clothing and under clothing are strewn in the bushes along the road. How did these get here?

60. A formerly brilliant wizard, now pesters the party with the incoherent rants of a man driven mad by a botched invisibility spell.

61. A drunken dwarf staggers along, challenging everyone to a wrestling match.

62. A goblin, on fire, runs shrieking past the party.

63. A rock with an odd, glowing rune sits by the road ahead.

64. A noble, disguised as a filthy beggar, tests the party’s compassion and generosity. If they pass whatever standard he sets, then he becomes a source of various quests that require personal sacrifice to accomplish.

65. A circus is set up alongside the road. A barker on the roadside cajoles you to “come inside and see what wonders it holds.”

66. The road crests a hill, and spread out before the group is a stunning, sweeping vista of the land beyond. A painter sits nearby, capturing the scene, and asks the group to pose for his foreground.

67. An overturned rowboat sits on the side of the road. There is no river or stream nearby. Under the rowboat is an entrance to a lair.

68. A wandering cleric begs the heroes to recover a relic for them.

69. A road sign saying where you came from is ahead of you.

70. A group of guardsmen hang wanted posters on trees. One face looks familiar to a PC.

71. A carriage is stuck high up in a tree.

72. In the morning while breaking camp, the PCs spot a bush that wasn’t there before.

73. A beautiful woman, adorned in the robes of an enchantress, emerges from hiding near the road and implores you to lend her aid.

74. The road is lined with snakes sleeping in the sun.

75. A necromancer uses his talents to animate animal and human corpses and forces them to perform in a roadside circus. The townsfolk from a nearby village seem to enjoy the show a bit too much.

76. A chain gang digs ditches beside the road.

77. A traveling minstrel challenges the wisest looking member of the party to a storytelling contest.

78. A wizened tinker sells charms from his cart: dried frogs, finger bones, cat skulls, and the like. Leaving him, you turn to find he is eerily out of sight altogether.

79. A paladin of a holy church and his retinue have ridden out on a holy crusade against evil and demand others who serve the cause of good to join their cause on the spot.

80. The road starts to get muddy. Soon the mud is two feet deep. Water in the ditches alongside starts to bubble.

81. A majestic elk sprints past with something golden caught in its antlers.

82. A stranger on the road tells each PC to repent of their sins. He knows details.

83. A door stands beside the road, but there is no sign of the rest of the house.

84. A wine merchant’s wagon has shattered a wheel and he offers passers-by cut rate prices on his wares as it is getting repaired.

85. An ugly old woman struggles to bring her wash basket of wet clothes up from the creek to the road. She stumbles and drops the laundry back down the slope.

86. A monk, collapsed and bleeding on the roadside, pushes an unremarkable ring into a PC’s hands and desperately whispers, “You must…” before exhaling his last breath.

87. A lost gnome asks for directions.

88. A dead raven lies on the road, pierced by a bright blue fletched arrow.

89. A table on the roadside holds a large basket of fresh vegetables. A sign reads “1 copper a bunch: honesty is a virtue!”

90. You find a small leather bag. It smells of moisture, and contains a set of keys and a vellum map to the location of a small keep.

91. The road is littered with bear traps.

92. A thick fog has settled on the bridge ahead.

93. The group arrives late at night at a tiny village straddling the road. They secure accommodation and food from the friendly locals and fall asleep. In the morning the village is empty and ruined, as if abandoned years ago.

94. As the road passes through a hilly region, you spy a cave, from which can be heard the voice of a singing female.

95. As you turn the corner, a dwarf and elf are standing over a stack of goblin corpses. They argue over the kill count.

96. The party notices a sudden and drastic change in temperature, then just like that, things are back to normal.

97. A little girl is watching you from just off the road. The next time you glance over, you see a wolf run away.

98. An ecstatic farmer presses a cigar into your hands and proclaims, “It’s a girl!”

99. Scratched into the dust of the road are the words, “Good luck tomorrow. You’re going to need it.”

100. The entire party suddenly loses their bearings and realize that they’ve walked the same mile three times. Are they road weary or are they caught in something manipulating them.

Enjoy. if you want more encounters, check out the work of Johnn Four .  Or give our 100 City Encounters  and 100 Forest Encounters lists a look!

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100 Riveting D&D Random Road Encounters

travel encounters for dnd 5e

Venture forth on the well-worn trails and hidden byways of your fantastical realm with this comprehensive compendium of 100 D&D random roadside encounters. As a diligent Dungeon Master, ready your wits and conjure your unique brand of enchantment to breathe life into these captivating travel scenarios.

Within this page lies a vibrant mosaic of unexpected interactions, each crafted to ensnare the imagination and inject a pulse of exhilarating spontaneity into your campaign. From the eerie stillness of a ghostly procession to the boisterous challenges of tavern-bound travelers, our thoughtfully curated list invites your party to an array of rich experiences that lie just beyond the bend.

Forge narratives steeped in intrigue and wonder as your adventuring party faces the uncharted whims of destiny. Will they parley with silver-tongued merchants, conspire with secretive cabals, or draw swords against hidden foes? This list is your springboard to limitless adventures that will leave your players riveted, eager for the next revelation along their journey.

Arm yourself with these imaginative traveling encounter ideas, and elevate the path less traveled into a legend that will echo through your players’ memories. Let the dice roll, and let the stories unfold, as each step on the road brings with it the promise of glory, treachery, and the unbreakable bonds forged in the heat of shared adventure.

100 Random Roadside Encounters

Embark on a journey teeming with chance encounters and roadside intrigue! Our list of 100 Random Roadside Encounters is the quintessential guide for any Dungeon Master who seeks to enrich their world with spontaneous moments of adventure and unpredictability. Whether it’s a cunning ambush by goblin raiders or the mysterious allure of a wandering minstrel’s song, this treasure trove of dynamic scenarios is designed to seamlessly weave into your campaign, ensuring that no two travels are ever the same.

As your party traverses the untamed wilds or well-trodden paths within your realm, this curated collection offers a vibrant tapestry of potential interactions, each brimming with storytelling opportunities. From the haunting wails of a tormented spirit to the hearty laughter of dwarven revelry, these encounters beckon adventurers of all stripes to engage with the living, breathing world you’ve crafted.

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Perfectly suited for both seasoned veterans and those just beginning their foray into the rich universe of tabletop role-playing games, this list ensures that around every bend lies the possibility for excitement, danger, and tales yet untold. So ready your dice and let the road rise up to meet your players, where fate may smile upon them or where peril awaits with bated breath.

1) You come across a hexagonal hay wagon pulled by three cows with the sound of a bard playing inside. If you approach, you are offered a ride.

2) A man in beggar’s clothing asks for your help. He claims to have been cursed by the local Duke because he witnessed the Duke murdering his wife.

3) You come across a group of acrobats performing. If you join them and give them a show of your own skill, they will invite you to join their circus

4) You come across a riverboat with a sign advertising passage to the next town.

5) You see a woman standing by a tree, holding a bundle. She asks you to hold it for a moment, and she runs off. When you open the bundle, you find a newborn baby.

6) You come across a troll passed out on the side of the road.

7) You come across a horse whose rider has fallen off. The horse will let you mount him if you can wake him up.

8) You come across the burnt remains of a wagon.

9) You see a man in armor, waving his sword in the air, demanding that people move out of the way.

10) You see three men in animal masks, juggling fruit.

11) You come across a blacksmith, who claims that he will pay you to watch him while he runs errands.

12) You come across a man who invites you to play a game. If you win, you get a prize. If you lose, you owe him a favor.

13) You come across a group of people arguing about a hill giant.

14) You see a group of large men standing around a pit.

15) You see four men dressed in black, riding horses.

16) You see a wagon being pulled by a giant snail. A wizard tips his hat as he passes.

17) You come across a group of young men parading down the road dressed in costumes.

18) You see a group of women walking down the road. They are singing a song about a famous battle.

19) You see a group of people painting a wagon at a crossroads.

20) You see a man and a woman standing next to a wagon, arguing. If you tell them to make up, they will ask you to choose their punishment.

21) Two men are arguing about a goat.

22) As you walk along the road, you see a gleaming red gem. If you touch it, you will instantly turn into a gem that can talk for 2d20+20 days.

23) Two men are arguing about the value of a bridge. If you offer to buy it, one of them will sell it to you for 10 silver pieces.He does not own the bridge. He’s just hungry.

24) You see a loaded cart that is trapped. If you touch it, it will explode. A group of 2d8 bandits will then attack.

25) A cart is being pulled by a giant ox. The farmer riding in front says, “Hello! Goodbye!”

travel encounters for dnd 5e

26) As you approach a barn, someone comes out and invites you in for some cider. If you drink it, you will be poisoned.

27) You come across a group of young men on their way to a feast. They will invite you to come along with them, but the feast is held in the basement of an insane cult leader who will force you to eat human flesh.

28) You come across a wineskin on the side of the road. It never runs out of wine.

29) You see a man carrying a large wooden box. He will offer to give it to you, but he wants you to answer three riddles. If you fail to answer, he will become enraged and attack.

30) You see a cleric of a god you don’t believe in. If you insult him, he will challenge you to a debate.

31) You see a farmer who claims to have been cursed. As you watch him, he transforms into a unicorn and trots away.

32) You see a man arguing with a boy. If you intervene, the man will thank you and the boy will attack you.

33) You see a dead rabbit on the side of the road.

34) You see a man carrying a board that has a long message written on it. It is a letter from a father to his son. If you stop to read it, he will steal something of yours that you will never get back.

35) You see a sign that says, “Fork in the road. Go left.”

36) A man dressed in black is standing in the distance. If you approach, he will ask you if he can buy your soul for 1,000 gold pieces.

37) You see a stack of coffins. They are all empty.

38) You see a barn painted on the side of the road. A board is nailed to the wall that says, “Welcome to Barnsville. Population 37 rats!”

39) You see three old men carrying a heavy load down the road. If you help them, they will invite you over for dinner. They are three brothers.

travel encounters for dnd 5e

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40) A bunch of men are standing in the road, arguing about a wooden barrel.

41) You see a man carrying a bucket with a sign that says, “I am lost. Will you show me the way to the nearest tavern?” If you agree, he will follow you around for the rest of the day, slowing you down.

42) You see a man in the distance, waving his arms.

43) You see a group of prostitutes. They will ask you to help them carry their supply of cocoa leaves to the local brothel. If you help, they will then ditch you.

44) You see a group of men praying at a crossroads. If you join them, they will ask you to pray to their god. If players do not, they will attack.

45) You come across a man digging a hole. When you ask him what he is doing, he says that he is burying a vampire queen who was killed by a paladin. He’s actually burying his mother in law.

46) A man is standing in the road with a sign that says, “I’m lost.” If you try to give him directions, he will demand donations.

47) You see a group of men arguing about what to do with a sheep.

48) You see a group of horsemen. If you approach them, they will ask you to join them in a battle.

49) You see men dragging a large wooden barrel. They are too drunk to explain what is in the barrel, but it is heavy and is not beer.

50) You see a group of men tossing a ball around. If you join in, it will quickly become very competitive.

D&D Random Road Encounters

51) You see a group of farmers arguing about what crop to plant.

52) You see a group of men carrying a dead man behind them.

53) You see a group of young men singing songs.

54) You see a man in the distance. He’s very angry at someone named “Dave.” He will engage players in conversation, angry about Dave, until he is calmed/lied to, or he is given directions to find Dave.

55) You see a group of men digging a hole. When you ask them what they are doing, they say that they are burying their friend, who has been gravely injured. They are actually burying a fallen member of their group.

56) You see a man in the distance. He is walking with a limp. If you approach him, he will tell you that he has been attacked by a group of men, who stole his money and kicked him in the shin really hard. Really hard!

57) You see a group of young men examining an old helmet, with various things growing out of it, including plants, fungi, and insects.

58) A group of 2d4+2 men dressed in colorful clothing and masks are chasing a wild pig. They will challenge players to try and catch the pig, and if they succeed, they will be invited to a feast.

59) You see a group of crying young boys and girls. “Our parents were taken away by an ogress! It was horrible!”

60) You see a group of children near a dead campfire. They will ask the players to listen to their tale of woe. The children are offspring of the 2d8 bandits hiding nearby.

61) You see a group of young men who are apparently fishermen. They do not have any fish, but they do have a fish shaped hat and fish shaped shoes. They claim to be from the future.

62) You see a group of men fighting over a piece of food. They will attack the party if not fed.

63) A small group of 2d4 young men are playing catch with a live chicken. The chicken is not enjoying the game.

64) You see a group of merchants in colorful clothing, with all sorts of trinkets and baubles for sale. They are supposedly the only source of the items that they are selling.

65) You see a group of men in the distance. They are in the middle of a game of chess. They will challenge the party to a game of chess for their lives. They take the game very seriously. The chess board and pieces are actually cursed.

66) You see a group of rangers in full camouflage. They’re embarrassed when you notice them.

67) A group of 2d4+1 men in matching clothing are having an arm-wrestling competition on the side of the road. Betting is encouraged.

68) Two elderly women are gossiping about a group of men involved in a nearby trial. The players are welcome to listen in.

69) You see a group of young men. They are drunk, but are polite. If the players are also drunk, the men are belligerent.

70) An old beggar is lying on the side of the road.

71) You see a group of men running away from something. It is unclear what they are running from. They do not stop.

72) You see a group of men and women inspecting a dead body. They are very upset and will not allow the party to investigate the body.

73) As you continue down the road, you hear a loud noise from ahead. It sounds like a wagon full of gears and scrap metal is careening down the road. A traveling gnome trinket offers to sell you his wares.

74) You hear a loud squawking from above. A large vulture is circling the party.

75) A man in a wagon is asking for protection to rest for the night. He has a large amount of gold in a chest.

76) A group of men is in a wagon. They are insane and will not let you pass.

77) Up ahead, you see a group of men in a wagon.

78) There is a group of men at the side of the road arguing over some gold.

79) A group of men are on horseback arguing with a merchant.

80) As you travel you hear a loud snorting sound. A large wild hog is rooting through the bushes nearby.

81) A large wild boar is sleeping on the side of the road.

travel encounters for dnd 5e

82) A goblin is standing at the side of the road, at first glance he appears to be a small, human boy begging for food.

83) An elven bard and a halfling spy have been captured by a group of slavers and are being taken to a nearby fortress.

84) There is a small pond with a few ducks swimming in it.

85) A large black pig is rooting through the bushes.

86) A large black bear is standing at the side of the road. The bear looks healthy and well fed.

87) A group of young children are playing a game of “Hide and Seek” in a nearby field.

88) A group of children are running through the forest, laughing and playing tag.

89) A group of children are playing a game of tag in a nearby meadow.

90) A group of adults are having a discussion in a small clearing. You can’t quite make out what they are discussing.

91) A woman carrying a basket is walking down the road.

92) A maiden is sitting on a rock at the side of the road looking sad.

93) A small cottage is in the distance, smoke is billowing from the chimney.

94) A small house is on the side of the road with a sign that reads “Cobblestone Inn”.

95) A small dog is barking at you from behind a fence.

96) A horse is grazing on the side of the road.

97) A horse-drawn wagon is stalled in the road. A man is arguing with a farmer.

98) A shepherd is herding a flock of sheep down the road.

99) A small dragon is sitting on the side of the road playing with a pile of rocks.

100) A small black kitten is sitting by the side of the road. It hisses right before a witch appears and attacks.

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travel encounters for dnd 5e

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D100 Great DND Travel Encounters for 5e

travel encounters for dnd 5e

Need some great DND travel encounters? I’ve got you covered! And if you enjoy this list of one hundred encounters while traveling, be sure to read to the end for even more great D&D tools to use in your campaign.

100 DND Travel Encounters

  • A Elf Scout is running towards the players with a panicked look on his face. He is about to be attacked by 2d4+2 Giant Spiders. The players can help him defeat the spiders, or leave him to die.
  • A group of halflings are running away from a group of kobolds. The kobolds are about to catch up with the halflings. The players can help the halflings, or help the kobolds catch the halflings.
  • A group of people are gathering around a merchant’s wagon. The merchant is selling a rare and valuable item. The merchant is asking for an outrageous price for the item. The players can try and buy the item for less than the merchant’s price, or the players can try and haggle with the merchant for a lower price.
  • A group of villagers are gathered around a fire. The villagers are telling stories about a nearby dungeon and the dangers within it.
  • A group of people are gathering around a new statue that has been recently erected in the city. The statue is of a famous hero from the city’s past. The players can learn about this hero’s history by listening to the people talking around the statue.
  • A group of children are playing with a ball. The ball rolls into the street and is almost run over by a wagon full of goods. The players can help the children get their ball back, or not bother helping them.
  • A man is trying to sell the players a map to a nearby dungeon. The man claims the map is a copy of an original map that was discovered within the dungeon. The man is lying and wants to trick the players into buying a worthless map.
  • A group of people are gathered around a new statue that has been recently erected in the city. The statue is of a king from the city’s past. The players can learn about this king by listening to the people talking around the statue.
  • A man is trying to sell the players a map to a dungeon. The man claims the map was drawn by a famous explorer who has been lost in the dungeon for many years. The man is lying and wants to trick the players into buying a worthless map
  • Hordes of giant grasshoppers attack. They will ambush the players from behind and surround them. Players will need to fight through hoards of giant grasshoppers to continue on. This encounter can be used as a way to introduce the players to the horrors of the grasslands.
  • A young and lost drow wanders near the players. If the players approach, he will run away. If players chase him, they will find him dead at the end of the trail. If they approach again, they will find an ambush of 20 kobolds.
  • The players find a group of 5 human bards. They were traveling through the grasslands when they were attacked by a group of kobolds. They are lost and need help getting back to their home city. They are desperate and will try to con the players into helping them.
  • A group of 3d6+3 bandits are attacking a group of 3d6+3 farmers. They are fighting over the farmers’ supplies. Players can choose whether to help the farmers or the bandits.
  • Five wandering human wizards are searching for ingredients for their spells. They are lost and need help getting back to their home city. They will tell the players what they are looking for and offer to pay them for every ingredient they bring back to them.
  • A group of 3d6+3 traveling merchants are transporting a wagon of goods through the grasslands. They are lost and need help getting back to their home city.
  • A group of 2d6+2 farmers are traveling through the grasslands in search of a better place to farm. They are lost and need help getting back to their home city.
  • A group of 2d6+2 old women are traveling through the grasslands in search of a better place to live. They are lost and need help getting back to their home city.
  • Litter of 3d6+6 wolf puppies. They are not aggressive, but they are very hungry.
  • A single old man. He is a retired bard. He has no teeth and wears no shoes. He asks for food and money. He is a con artist. If players give him money, he will vanish. If players give him food, he will sing for them. He is not a good bard, but he is a good con artist.
  • A random arctic encounter with a band of 2d10 wolves. They seem to be stalking something, but it is unclear what.
  • A group of 2d4 hunters are out looking for game. They are wearing leather armor and carrying bows. They will ask if the players have seen any game in the area. If players say no, they will ask to join them on their hunt.
  • A group of 2d4 soldiers are patrolling the area. They are wearing chainmail and carrying shields and swords. They will ask if players have seen any orcs in the area. If players say no, they will ask to join them on their patrol.
  • A group of 2d4 soldiers are patrolling the area. They are wearing chainmail and carrying shields and swords. They will ask if players have seen any orcs in the area. If players say yes, they will ask to join them on their hunt.
  • A group of 2d4 merchants are traveling from town to town selling their goods. They are carrying various goods including: cattle, sheep, pigs, chickens, goats, horses, etc.
  • A random encounter with a band of 2d10 orcs. They are carrying various items including: sacks of grain, sacks of potatoes, sacks of flour, sacks of oats, sacks of carrots, sacks of apples, etc.
  • A group of 2d4 hungry humans are looking for food. They are carrying various items including: sacks of grain, sacks of potatoes, sacks of flour, sacks of oats, sacks of carrots, sacks of apples, etc.
  • A group of 3d4+3 humans are looking for a place to settle down. They are carrying various items including: sacks of grain, sacks of potatoes, sacks of flour, sacks of oats, sacks of carrots, sacks of apples, etc.
  • Wagon of hay with 2 dwarves sitting on the hay. Inside the hay are 4 goblins. The dwarves are on their way to the nearby city to sell the goblins. They will not sell the goblins to you. They will fight you instead.
  • A horse-drawn cart full of turnips and a human farmer. The farmer will offer you some of his turnips. If you accept them, then a nearby turnip patch will have a major turnip blight and the farmer will be ruined. If you refuse them, the farmer will get angry and attack.
  • A horse-drawn cart full of apples and a human farmer. The farmer will offer you some of his apples. If you accept them, then a nearby apple tree will have a major apple blight and the farmer will be ruined. If you refuse them, the farmer will get angry and attack.
  • A wagon full of apples and a human farmer. The farmer will offer you some of his apples. If you accept them, then a nearby apple tree will have a major apple blight and the farmer will be ruined. If you refuse them, the farmer will get angry and attack.
  • A merchant cart full of copper coins and a merchant. The merchant will offer you some copper coins. If you accept them, then the merchant will be robbed and killed by bandits later that night. If you refuse them, then the merchant will get angry and attack.
  • A wagon full of hay, a dwarf, and 4 horses. The horses are pulling the wagon full of hay along the road to a nearby city where they will be sold. The dwarf is watching the horses and making sure they don’t stray too far from the wagon. He is not interested in talking to anyone and will attack if provoked.
  • A horse-drawn cart with a human selling cooked chickens and potatoes. He will offer you some cooked chicken and potatoes if you give him 10 copper coins per meal. He will not accept any other currency. If you pay him, then he will run off with your money and become a low level bandit later on.
  • A horse-drawn cart with a human selling cooked chickens and potatoes. He will offer you some cooked chicken
  • Unexpectedly, a caravan of one hundred mules and horses, led by one hundred men armed with axes, swords, and bows, storms onto the road. They are from a large kingdom and are on their way to a nearby city. They are on their way to trade merchandise with the residents of this city. They will not stay for long.
  • The players see a group of one hundred men and women, led by one hundred men and women, running to the east. They are fleeing from a group of one hundred men and women, led by one hundred men and women. The band of refugees is seeking the safety of the nearby city.
  • A group of seven men and women, dressed in black robes and hoods, rush by on their horses. They are carrying a large chest that they are trying to hide from the players.
  • A group of five elderly men and women are sitting by the side of the road. They are sitting around a small campfire, roasting a rabbit or squirrel on a stick. They will ask the players to join them for lunch. They will offer the players advice on the best way to get to the nearby city safely.
  • A group of three men and women are sitting by the side of the road. They are sitting around a small campfire, arguing about the best way to get to the nearby city safely. They will ask the players for their advice on the best way to get to the nearby city safely. They will then follow the players, thanking them for their help.
  • The players see a group of two men and women, led by one man and one woman, sitting by the side of the road. They are sitting around a small campfire, roasting a rabbit or squirrel on a stick. They will ask the players to join them for lunch. They will offer the players advice on the best way to get to the nearby city safely.
  • The players hear a loud sound coming from the sky. Looking up, they see a large flock of birds flying overhead. As the flock passes overhead, one bird drops a small object on the players. It is a small, leather pouch. If the players examine the pouch, they will find it contains ten copper pieces.
  • The players hear a loud sound coming from the sky. Looking up, they see a large flock of birds flying overhead. As the flock passes overhead, one bird drops a small object on the players. It is a large sack containing ten pounds of wheat or potatoes.
  • The players see a group of four men and women, led by one man and one woman, rush by on their horses. The four riders are carrying what appears to be a dead body on the back of their horse. The body is covered by a blanket.
  • The players see a group of 2d10 gnolls on the warpath.
  • I smell something cooking… It smells like bacon… Oh, it’s a group of Halflings cooking breakfast for themselves and the players. They are on the road to their new home. They are travelling with a wagon full of their belongings.
  • A group of men with spears are running toward the players. It looks like they are running from something…
  • A man with a large bird cage with a bird inside it is running toward the players. It looks like he has been chased by something…
  • A large rock is on the road. It is laying on its side. It looks like it was recently dropped…
  • A man is walking along the road. He is carrying a large bag of feed. He is walking to his farm. He has been doing this for many years. He knows the area well and can give players directions if they ask him. He has no knowledge of the nearby dungeons or ruins .
  • A group of 5 men are walking along the road. They are carrying swords and shields. They are on their way to the local city to join the local city guard. They are practicing their swordsmanship along the way.
  • A group of men is standing near the road. They are waiting for the players to pass by. They are standing in the road and they are holding swords, ready to attack players if they are approached by them.
  • A man with a donkey is walking along the road. He is carrying a large jug of wine. He is heading toward a nearby inn to sell his wine to the innkeeper there who pays him well for the wine he brings him.
  • A group of 3 men with swords and shields are walking along the road. They are on their way to the local city to join the local city guard. They are practicing their swordsmanship along the way.
  • A man with a donkey is walking along the road. He is carrying a large bag of feed. He is walking to his farm. He has been doing this for many years. He knows the area well and can give players directions if they ask him. He has no knowledge of the nearby dungeons or ruins.
  • Unexpectedly, the party comes upon a group of 3d6 acolytes who are traveling on the road to a nearby temple. If players talk to them, they will give the players a map to a nearby dungeon that they have found while exploring.
  • A man is walking down the road with his dog. He is headed towards the nearest village. The man is named John and he is an ex-soldier. He lost his home in a war and has been searching for a new home for him and his dog. His dog is named Fido.
  • The party comes upon a group of 3d4+4 goblins playing a board game. If players approach them, they will challenge them to a game of their board game. If players lose, the goblins will rob them of their possessions!
  • The party sees a group of 3d4 skeletons riding horses. If the players approach, the skeletons will attack and if possible, ride away on their horses.
  • A group of 3d4+4 gnolls carrying spears are walking down the road. If players approach, they will attack!
  • The party sees a group of 3d6 human soldiers. They are carrying swords and shields. They are headed towards a nearby village to fight in a war. They are unaware that they are headed towards their own death.
  • A group of 3d6 farmers are walking down the road with their axes and shields. They are traveling to a nearby village to harvest wheat and bring it back home. They will give the party a small reward if they help them harvest their wheat.
  • Two female elves are walking down the road. They are headed towards a nearby village. They are carrying bows and arrows. If players talk to them, they will tell the party that they are hunting for food for their village.
  • A group of 3d6 gnolls carrying spears are walking down the road. If players approach, they will attack!
  • A group of 3d6 humans are walking down the road with their swords and shields. They are headed towards a nearby village to fight in a war. They are unaware that they are headed towards their own death.
  • Wagon full of dwarven traders, who are selling their goods.
  • A pack of wild dogs are chasing a farmer’s sheep.
  • A lone farmer is standing in the middle of the road. He is standing there, holding a small box. He will ask the players if they want to trade with him. If they do, they will find out that he wants to trade them one of their chickens for the box, which holds a small magical dragon that will follow them around if they agree to the trade. If they refuse, he will try to attack them with his two sheepdogs.
  • A group of 5 mercenary soldiers are standing near the side of the road. They will ask the players if they want to hire them as bodyguards for a price of 10 gold pieces per day.
  • A man named Joe is standing in between two trees, holding a sign that reads ‘I will work for food’. If players give him food, he will follow them around until they get rid of him.
  • A group of five traveling minstrels are standing next to their wagon, which holds their instruments and their food supplies. They are looking for somewhere to perform with their band.
  • A pack of wild dogs are chasing a farmer’s sheep. If players help the farmer, he will give them 1d4 silver pieces. If they help the dogs, they will get 1d4+1 silver pieces from the Pack Leader.
  • A traveling merchant is looking for someone to escort him to a nearby town, because he has some goods that need to be sold there, but he is too afraid to travel alone because of recent bandit attacks along this stretch of road.
  • A group of 2d6 farmers are walking down the road towards a nearby town. If players ask, they will tell them that they need to sell their harvest in the city and then they will be going home again.
  • A group of two men are walking down the road, talking about how they spent all their money in the last town and now they have no money left for food or lodging and now they have to walk all the way back home again because no one will give them work because they have no money!
  • Orog scouts have spotted the party and are preparing to attack. They are riding wargs and have several other orcs with them, who are mounted on wolves. The orcs and wolves will attack, but the wargs will wait until the orcs are dead before attacking. If the party does not attack the orcs first, then they will retreat after losing two orcs.
  • A group of men is walking down the road. They are carrying a statue of a horse. If the party asks, they will say they are taking it to a nearby village. If they are asked to rest, they will say they can’t because they must get the statue there before dark.
  • The party sees a man carrying a large jug of wine. If they ask, he says that he is taking it to a nearby village where he will sell it and make a profit.
  • A man is walking down the road. He appears to be lost and is looking around, obviously confused about the direction he is going in. If asked, he will say that he is trying to find his way back to his village but got lost because he was busy thinking about something else and did not notice that he was going in the wrong direction.
  • A dog barks at something, but nothing is there. The dog will bark at this spot again if the party comes back this way later.
  • A group of men is walking down the road. They are carrying several large statues of horses. They will tell anyone who asks that they are taking them to a nearby village where they will sell them for a profit.
  • Two men are walking down the road, carrying a large chest between them. They will tell anyone who asks them that they are taking it to a nearby village where they will sell it for a profit.
  • A man is walking down the road, carrying a large sack of coins over his shoulder. If asked, he will say that he is taking them to the nearby village where he will sell them for a profit.
  • A group of men is walking down the road. They are carrying several large chests between them. If asked, they will say that they are taking them to a nearby village where they will sell them for a profit.
  • A man is walking down the road, looking around nervously as if he is expecting to be attacked any moment. He is carrying a large chest between his arms and looking around nervously as if he is expecting to be attacked any moment but does not appear to be armed or ready to fight or defend himself if attacked by anyone at all despite looking around nervously as if he is expecting to be attacked at any moment.
  • Lava flows have blocked the roads. The party sees a group of five humans who are attempting to clear the path. They are wearing chain mail, but they are not armed with weapons. They have shovels and axes.
  • A group of 4d6 humans are fleeing from a pack of 3d10 wolves.
  • The party sees a group of 4d6 humans who are fleeing from a pack of 3d10 wolves. They are carrying sacks of valuables.
  • A pack of 4d4 wolves are attacking a flock of sheep. The flock is guarded by a shepherd who is armed with a sling and a staff.
  • The party sees a group of 4d4 deer who are grazing near a pool of water. There is a group of 4d4 humans who are hunting the deer.
  • A group of 4d4 orcs are riding on horses, they are riding towards the party lashing out with lances and spears at any human they see.
  • The party sees a group of 4d4 humans who are hunting deer.
  • The party sees a group of 4d4 humans who are hunting deer. They are dressed in leather armor and they carry bows and axes.
  • A group of 3d6 bandits are riding on horses, they are riding towards the party lashing out with lances and spears at any human they see.
  • 1d6 goblins are trying to steal an animal from the party’s cart. (If they don’t have an animal, one snuck in.)

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Related Random Tables RPG Gems

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  • D100 Random Castle Encounters 5e DND+
  • 100 Random 5e DND Travel Encounters
  • Random Travel Encounters Table DND 5e
  • Leonin DND 5e: 100+ Names and Generator for Tabletop RPG
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Paul Bellow

Paul Bellow

IMAGES

  1. D100 Great DND Travel Encounters for 5e

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  2. On the Road: Wilderness Travel Encounters for DND 5e

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  3. 100 Random 5e DND Travel Encounters

    travel encounters for dnd 5e

  4. Random Travel Encounters Table DND 5e

    travel encounters for dnd 5e

  5. 100 Travel Encounters for 5e DND

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  6. An encounter map in the mountains [30x40] [OC] : r/DnD

    travel encounters for dnd 5e

VIDEO

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  2. Real Time Travel Encounters That Changed History

  3. Using Alignment Better! #short #dnd

  4. Can a Fighter Cast Time Stop?

  5. When Alignment is just a GIMMICK #short #dnd

  6. Using Alignment to Fool yourself! #short #dnd