100 Random 5e DND Travel Encounters

Breathing life into the journeys of your 5e DND characters and enhancing the depth of your roleplaying world just got easier and more exciting. Our meticulously crafted D100 random encounter table is designed to infuse your fantasy tabletop RPG campaigns with a rich variety of engaging and unique travel encounters.

From mystical encounters in enchanted forests to unexpected challenges in desolate wastelands, our table offers a diverse range of scenarios that cater to any travel setting in your world. Whether you’re a seasoned Dungeon Master or just starting out, these encounters are versatile and easy to integrate, ensuring every journey is filled with memorable moments and thrilling adventures.

AI + Procedural Generation = Worldbuilding Tool of your Dreams...

Coming soon to LitRPG Adventures Workshop...

Or check out my ChatGPT Backstory Generator

Feel free to adapt and weave these encounters into your campaign, creating a vibrant and dynamic storytelling experience for your players.”

100 Random Travel Encounters 5e

Embark on a journey through a world teeming with intrigue and wonder, where the path less traveled is strewn with possibilities. Along weathered roads and whispering forests, every corner you turn offers a chance for new encounters—each a story in the making, an adventure awaiting.

From mysterious merchants peddling exotic wares to lost souls seeking redemption, this collection of roadside encounters offers a tapestry of narratives to enrich your travels. Here, you’ll find a hundred carefully crafted scenarios that promise to breathe life into your journey, turning every moment on the road into a memorable experience.

Whether it’s aiding a cursed wanderer, unearthing the plots of vile bandits, or crossing paths with whimsical creatures of the wood, these encounters are designed to spur creativity and inspire storytelling. Prepare to meet unlikely allies, face moral quandaries, and discover hidden treasures—or hidden dangers—under the open sky or amid the tangled underbrush.

So tighten your boots, ready your wits, and set forth on the road. Adventure awaits those brave enough to seek it, and no tale is too small to be told. Welcome to a realm where every roadside meeting can change your destiny, for this is the land of endless possibility.

DND Random Travel and Roadside Encounters

1) Players encounter a small, wounded horse with a saddle and markings indicating it belongs to a local lord. The defensive animal may attack the players out of fear. If the players manage to heal and calm the horse without causing further harm, they find the horse is worth 70 gold, rewarded by the grateful lord.

2) A patrol of soldiers is searching for local bandits. Interaction with them reveals their mission and the possibility of acquiring provisions like food and water. They may also have information on the bandit’s last known location, which could assist the players if they wish to track them.

3) Local farmers are busy in their fields but are hospitable and will share food and water with the players, perhaps sharing local news or the lay of the land, which could be invaluable for navigation.

4) Women working for a nefarious wizard disclose his cruel experiments, turning children into lizards. Stopping this wizard could save the children and earn the players their loyalty, potentially adding new and grateful allies to their party.

5) A lost child seeks assistance in finding his parents, who were victims of the wizard’s curse. Helping reunite the family would not only earn the players valuable information about the wizard but also strengthen their reputation as heroes.

6) Concerned townsfolk outside a building inform players about a missing woodcutter believed to be captured by goblins. Investigating this could lead to a rescue mission and a thankful community, possibly with a reward.

7) Fishermen by a pond offer a moment of respite, sharing ale and food with the players, a chance for the group to gather information and rest before continuing their journey.

8) Farmers in the field generously offer food and water, perhaps along with knowledge of the surrounding area, including information on weather patterns and geographical features that players may face.

9) Hunters around a campfire are willing to share their meal and tales of the land. They could provide tips on tracking and surviving in the wild, or even alert the party of nearby dangers.

10) A traveling merchant with his daughter and a donkey cart appears. His inventory for sale is vast, and while he claims to offer items beyond what is visible, his honesty prevails in fair trade, potentially providing rare goods or masterful craftsmanship.

11) A one-armed woman with a broken leg beside a damaged wagon needs help. Aiding her could reveal her rich background and lead to a handsome monetary reward or insider knowledge of trade routes.

12) A robbed and dethroned king on the road seeks aid in returning to his kingdom. Helping him might not only result in a generous reward but could also secure a powerful ally or royal favor.

13) A man aims to sell 1d6+1 rat pups, their potential as trainable companions or for those looking for less conventional familiars making for an unusual business transaction.

14) Brunhilda, a woman cursed with a ghastly appearance, seeks help lifting the curse. Aiding her could lead to uncovering rare magical knowledge or an ally with potent, unknown abilities.

15) A horse trader, currently with a lame horse, doesn’t have the funds for a new one. Providing assistance could secure future trades at favorable rates or a dependable steed.

16) A band of seven disarmed soldiers seeks work or revenge on their banishers. Offering them a place in the party could bolster ranks for a significant venture or lead to a quest for retribution against a formidable adversary.

17) Brunhilda, apparently under duress, angrily confronts passersby. Soothing or assisting her could reveal her situation’s true depths, possibly leading to uncovering greater plots at work or the items of a powerful enchantress.

18) An eccentric man has an unusual array of rat pups for sale. Whether for curious buyers or questioning his motivations, this peculiar encounter could lead to uncovering a potential plot involving trained vermin or hidden treasures.

19) The same group of seven soldiers presents multiple options for collaboration—aid in returning home, assist in their vendetta, financial support, or self-defense. Their story could be intertwined with broader political machinations.

20) Four men isolated by choice remain aloof from influence and troubles. Their sage advice or possible insider knowledge could be invaluable, especially if players discover the reason for their solitude.

21) Vines entwined around a skeleton offer a clear warning of potential natural dangers in the area or a supernatural threat, urging cautious travel and possible discovery of a lost traveler’s belongings or cursed items.

22) An abandoned wagon with a dead horse may hold leftover goods from a raid or accidental tragedy—a chance to salvage goods but also a clue to lurking dangers or marauders nearby.

23) Two goblins in a dispute over a map might lead to treasure or a hidden location. Interceding could result in gaining a helpful guide or key information if players can settle the quarrel or outwit the goblins.

24) A man and his horse seeking directions to town may award guidance with appreciation or incidental information critical to navigating the area or a shortcut to their destination.

25) A funeral procession seeking help in burying their friend presents a chance for the players to pay respects and possibly discover the deceased’s history, affecting future encounters or uncovering hidden lore.

26) Young lovers picnicking offer shared company and a meal. Their innocence could offer a respite, but their presence might also be a sign of peace in the region or a prelude to a local legend coming to life.

27) Bandits scouting for a camping spot will rob those with gold. This unexpected threat could lead to confrontation or a tactical advantage if the players can outwit or negotiate with the bandits for safe passage.

28) Wedding attendees may become allies if the players are attending the event, or foes if not. Deft social maneuvering could turn this chance meeting into a valuable networking opportunity or even an invitation to a grand event.

29) Funeral attendees may treat the players with suspicion or welcome them as fellow mourners. Either way, the encounter provides a window into local happenings and influential families.

30) Wedding attendees in distress present an opportunity for the players to offer comfort or solve a mystery, potentially resulting in alliances or rewards.

31) A roving band of orcs presents an immediate threat; their aggressive nature demands a swift and potentially violent resolution or a strategic retreat, depending on the party’s strength and goals.

32) Traveling humans armed and ready for conflict suggest a region fraught with peril; their willingness to fight could point to recent hostilities or signal an upcoming encounter that may require the players’ intervention.

33) Roland, a job-seeking man with a bad leg, promises guidance and treasure knowledge for a wage. His specific skill set could be of great use for navigating treacherous areas or uncovering hidden riches.

34) Elderly women, victims of robbery by the notorious duo Bob and Bill, seek justice and the return of their possessions. Aiding them might reveal a local criminal network or lead to a heartfelt reward.

35) A group of goblins seeking supplies threaten violence. Their desperation could provide a chance for a truce and mutual aid, or players might have to fend off an attack and question their motives.

36) Fleeing kobolds offer an opportunity for linguistic exchange if players can communicate. Discovering what they’re escaping from might prevent future danger.

Apologies for the confusion earlier. Here’s the continuation from number 37:

37) Disguised as a beggar, an old man in tattered clothes offers the players riddles in exchange for coin. Solving his puzzles could reveal hidden treasures or unlock ancient secrets known only to a few.

38) A lively band of seven soldiers looking for work could become valuable allies if the players offer them a mission, or a threat if the players disregard them, leading to a sticky situation down the line.

39) Despite her intimidating screaming, Brunhilda is a beautiful but cursed woman in need of aid. Assisting her could lead to gaining a powerful magical artifact or the solution to a dark mystery in the region.

40) A peculiar man attempting to sell or feed an array of rat pups presents an ethical dilemma, potentially unearthing a strange new magic or a dark plague that threatens the land.

41) The same seven soldiers from before, armed and riddled with tales of exile, present a choice for the players to escort them home, aid their vendetta, or fend off a potential robbery.

42) Four men, secluded and around a campfire, speak of esoteric and occult matters, potentially granting arcane knowledge or foreshadowing a significant supernatural event.

43) An ominous sight of vines strangling a skeleton warns of hidden dangers, possibly leading to a haunted location or an artifact that binds the living with the dead.

44) An empty wagon with a deceased horse alludes to recent violence or plague. It may hold vital clues to prevent a wider disaster or lead to salvageable goods and lore about the lands.

45) A disagreement between two quarrelsome goblins over a map might be a chance to acquire guide services to hidden treasure or a cursed location that invites brave adventurers.

46) A lost man with his horse, seeking directions, offers an occasion for good deeds to be repaid with essential regional knowledge or a trusted future guide.

47) Mourners transporting a coffin beside the road might share local history and lore in appreciation if aided in their solemn task.

48) Two young lovers out for a picnic could offer a light-hearted break and share stories of local legends or rumors of treasure if the players join them.

49) A group of bandits looking for a suitable campsite could provide an encounter full of risk or opportunity, depending on the players’ actions and intentions.

50) A wedding procession invites or threatens the players depending on their response, potentially leading to alliances with local families or social entanglements.

51) A funeral procession, laden with gifts and sorrow, might reveal the area’s deeper stories or superstitions if the players pay their respects or offer assistance.

52) A party of wedding attendees in a despondent mood might seek the players’ help, hinting at a side quest involving family feuds or lost heirlooms.

53) A patrol of orcs searching for provisions offers a confrontation that could lead to battle, negotiation, or an uneasy alliance based on the players’ approach.

54) Human workers on the lookout for employment present a potential labor force for the players, or a disguised group with ulterior motives, creating a twist in the narrative.

55) A man named Roland, with a chest of treasures and tales, seeks employment as a guide, bringing an opportunity for adventure and wealth, if the players listen to his stories.

56) Elderly women, victims of thieves, present a quest for retrieval and justice, offering a storyline that could delve into the thieves’ network or reveal the women’s mysterious past.

57) Goblins eye travelers for potential loot, presenting danger and the chance to better understand the regional threats if the players engage or parley.

58) Babbling kobolds fleeing from terror could offer foresight into approaching hazards if the players can calm and communicate with them, or add a chase sequence to the adventure.

59) Gramps and Gramps, the elderly watchers from their hilltop perch, may provide warnings or prophetic guidance about dangers ahead, or requests for assistance that could lead the players onto a new path.

60) The traveling gnome women with a vegetable cart have much to barter and may share agricultural secrets or hints at fertile grounds for new endeavors or hidden groves.

61) The hunters on horseback, while seemingly aggressive, could share their vast knowledge about the local fauna and dangerous territories or entail a potential escort mission.

62) A demon-summoning cult performing incompetently presents a chance to prevent a great evil, learn a new dark secret or gain cursed items if the ritual is disrupted.

63) The card-playing group, while lacking in skill, could offer intriguing gossip, local intrigue, or a chance to win some easy coin and make new friends or rivals in the region.

64) A group of leonin collecting firewood is friendly and will allow the players to gather what they need, possibly hinting towards areas where magical or rare woods can be found, or where dangerous creatures lurk.

65) A group of villagers collecting water offers to share and trade stories. The encounter may lead to the discovery of a nearby water source with healing properties or the prelude to a local crisis involving the water supply.

66) Farmers in a field will protect their crops fiercely. Players can choose to assist them in exchange for a share of the harvest, learn valuable agricultural techniques, or gain insight into an ecological mystery affecting the crops.

67) A group of hobgoblins on giant dogs rides fiercely down the road. If the players manage to negotiate or follow them, they might discover the location of a hobgoblin outpost or the reason behind their aggressive patrolling.

68) A gathering at a roadside makes for a communal event; villagers invite players to join and warm themselves by the fire. The players could learn of local customs, festivities, or the dark secrets that some revelers might divulge in their merriment.

69) Brunhilda, once beautiful, curses every passerby due to her hideous appearance. Helping her find the source or remedy for her curse may grant the party a faithful ally with arcane knowledge.

70) A curbside sales pitch by a man with rat pups could turn into a breakthrough in pest control magic or an unexpected adventure into an alchemical experiment gone wrong.

71) Seven banished soldiers openly recruit; they offer to join the player’s cause, be it in seeking vengeance, reclaiming their homeland, or providing martial prowess in exchange for gold or other services.

72) An unusual tree along the road grows tall, with a luminescence and mysterious aura. It might provide magical substances or harbor secrets of an ancient druidic ritual imbibed in its rings.

73) Abandoned signs of villagers’ past trouble, like broken possessions and a burnt-out campfire, may lead to untold stories of a group’s misfortune, the remnants possibly holding forgotten heirlooms.

74) The ever-watchful pair of Gramps, looking out for trouble, offer the players advice and foreshadowing of perils ahead, telling tales of the area’s history or legends if prompted.

75) Momma, Ma, and Mango carting turnips harbor more than fresh produce; there could be hints at underground fey activities, smuggling routes, or simply the warm company of a home-cooked meal.

76) Patrols of rangers roaming the area suggest a tactical or environmental affair in the region. They might share skills, provide guidance, or recruit the players for a nature-focused mission.

77) A band of adventurers known for their malice and cruelty traverses the forest, potentially a group to rival or confront, each with their own ever-growing legend ready to clash with the players’ mettle.

78) Traveling bards en route to a local inn could be a welcome opportunity for collaboration, a jovial encounter filled with music and news from across the lands, or a seduction into a grandiose plot with the artists.

79) A stronghold occupied by sneaky bandits hints at a possible infiltration mission, a direct confrontation, or the uncovering of a regional crime syndicate with ties to the broader narrative.

80) A detail of elven travelers hints at peaceful trade or requests—perhaps an opening for diplomacy, learning exquisite arts, or the players becoming entangled in an ancient elven affair.

81) Thieves lying in wait present a potential trap and an immediate threat, opportunity for intelligence gathering, or the test of the players’ ability to navigate through deceit and stealth-driven engagements.

82) A roaming group of hobgoblins could signal a larger militaristic strife in the area, offering battle, tales of mighty conquests, or information about a pending siege or conflict zone.

83) Seeking employment, a small band of halflings equipped with various tools are ready to assist the players, offering their unique skills, knowledge of the local land, or even companionship for a fee.

84) A procession of soldiers ensures the road is secure—a sign of stability, or perhaps of martial law. They may share strategic information or seek recruits for the cause of the local lord.

85) As a group of merchants travels with great haste, their suspicion indicates they may not be as trustworthy as they seem. Dealing with them could reveal black-market trades, espionage, or forbidden knowledge if the players dare to dive deeper.

86) An unforeseen rainstorm pours down, presenting a survival challenge with the need for shelter or the chance to exhibit heroism by helping others caught in the deluge, earning goodwill.

87) The smell of fresh blood on the road guides the players to a brutal scene, a sign of lurking predators or a recent skirmish, and an introduction to a storyline of vengeance or survival.

88) An old man on a bench weaves captivating tales hinting at nearby dungeons and dragons. Whether fact or fiction, his stories may inspire the party to seek adventure or caution them against certain doom.

89) A snapped signpost, possibly a victim of monstrosity or angered entities, may provoke the players’ curiosity about what lies ahead or urge them to repair it, improving travel for all.

90) Remnants of an old, unattended campfire might be a mere traveler’s site or the mark of a secretive gathering, leaving clues for the players to uncover hidden gatherings or lost travelers.

91) Dusty tracks leading in and out of the forest beckon the players to follow the journey of an elusive creature or traveler, presenting an opportunity to track, hunt, or perhaps save someone in trouble.

92) Abandoned yet intact, a campsite lies forsaken in time. Exploring might yield lost journals, ancient relics, or uncover a tragic tale of a past expedition that may be connected to the players’ ongoing quest.

93) A mysterious tree with hard, stone-like bark seems out of place. Studying it may reveal that it’s a petrified ent or a beacon for a hidden druidic sect, offering secrets or an ally within.

94) A singular cow with an ethereal glow, possibly an enchantment or omen, may lead to a divine quest, cursed artifact recovery, or the birth of local myths starring the players.

95) An ordinary road stretches before the players, but a disquieting feeling looms, suggesting an invisible force, a magical threshold, or the precognition for an extraordinary event that awaits.

96) A man named Maugh, strong yet jobless, is willing to carry burdens for coin. Hiring him can ease travels and potentially reveal stories of lost caravans or secret traveler’s paths.

97) A man offering work named Entik is an outcast wizard, bringing the opportunity for magical tutelage, a dangerous spell, or uncovering a wretched excommunication from a mage’s circle.

98) A wandering man named Gorc seeks to lend his sword for hire. Dealing with him could bolster the party’s strength with his war tales, or unravel a disgraced warrior’s path seeking redemption.

99) Soldiers patrolling the region might be protectors against theft, or enforcers with ulterior motives. The players’ interactions could lead to uncovering conspiracies or allying with the local militia.

100) Two elderly women approach seeking help to reclaim their belongings stolen by robbers. Their narrative might interweave noble heritage, secrets of an ancient guild, or a heartwarming reunion.

Even More Travel Encounters for 5e DND

Want even more random encounters? Check out Random Encounters AI today. The site already has over 10,000 random encounters you can use for free – with more coming all the time. Check it out and find me on Twitter to let me know what you think.

AI + Procedural Generation = Worldbuilding Tool of your Dreams...

Coming soon to LitRPG Adventures Workshop...

Or check out my ChatGPT Backstory Generator

Paul Bellow

Paul Bellow

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