100 5e DND Random City Encounters: Best D100

Need some random city encounters? I’ve got a list of 100 here, or you can head over to Random Encounters AI for even more. I’ve been using GPT-4 from OpenAI to generate all sorts of RPG content for fantasy tabletop campaigns. Enjoy this list of random city encounters for Dungeons & Dragons, Pathfinder, or other tabletop RPG systems.

Random DND City Encounters for 5e, Pathfinder, or MERPs

Step into the bustling streets and shadowy alleyways of your fantasy cities with our collection of ‘Random DND City Encounters’. Perfectly tailored for 5e, Pathfinder, or MERPs, these encounters are designed to add an extra layer of depth and unpredictability to your urban settings. From mysterious merchants peddling magical wares to unexpected rooftop chases, each encounter offers a unique opportunity to enrich your storytelling and engage your players in the vibrant life of the city. Whether you’re navigating through the political intrigue of noble houses or dealing with the underbelly of the city, these encounters ensure that every city visit is filled with potential adventure and memorable moments.

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1) A man is selling maps of the city. The maps appear to be detailed and up-to-date, showing even the most recent changes in the streets and landmarks.

2) A group of men are grumbling about the ticket prices for a new play. They’re haggling among themselves, trying to determine a fair price before they approach the box office with an offer.

3) A group is lamenting their experience at a new tavern, warning others to avoid it due to poor service and watered-down drinks.

4) A man peddling sewer maps claims they’re accurate. His breath smells of strong ale, casting doubt on his reliability.

5) On the street corner, a vendor is selling what he claims are silver and gold jewelry at surprisingly low prices. Skepticism abounds but the offer tempts some passersby.

6) Locals discuss the bitter chill in the air, remarking that winter seems to be arriving early this year.

7) A group of halfling women debate the change in weather, insisting instead that the days are growing warmer, much to the confusion of onlookers.

Sure, I’ll go ahead and refine and expand upon the scenarios you’ve provided:

1) A map seller stands atop a crate, waving intricately drawn maps of the city for all to see. “Get your detailed city guides here!” he exclaims. The maps include notes on shortcuts, points of interest, and even recommended eateries.

2) Nearby, a group of middle-aged men lean against a wall, fervently discussing a new theatrical play famed across the city. Their brows are furrowed over the exorbitant prices, and they’re collectively brainstorming creative ways to get discounted tickets without appearing cheap.

3) At a tavern’s entrance, a few irate patrons are in the midst of a heated debate. They warn incoming customers about the poor quality of libations, advising against the house ale as strongly as though it were poisoned.

4) A scruffy man, with an unsteady gait and liquor on his breath, hawks old, stained maps he insists show the underbelly of the city—the sewers. The maps are a jumble of lines, and whether they hold any real value is anyone’s guess.

5) In a bustling square, a flamboyant character displays a tray of sparkling necklaces and rings, claiming they’re crafted with fine silver and gold. He assures potential customers of a “once-in-a-lifetime” discount, but there’s a clear air of deceit about him.

6) Wrapped in scarves and thick coats, a cluster of city dwellers exchange commiserations over the encroaching cold, some superstitiously claiming that an eternal winter is nigh.

7) Across from them, halfling women paint a different picture, confidently stating that spring is soon to bloom despite the visible frost. Their pleasant conversation about their gardens’ imminent blossoming provides a whimsical contrast to the chilly reality.

8) A shady figure in the shadows near an alley entrance entices thrill-seekers with maps to the city’s secretive catacombs, promising untold wealth to those who follow his leads. His assurance of riches from worlds beyond piques curiosity, even if such tales seem far-fetched.

9) A disheveled man with a tankard in hand sells similar sewer maps beside a pub. He swears by their accuracy with a drunken solemnity that makes it difficult to judge whether he’s a genius or a fool.

10) Three individuals stand by the smithy, engaged in a robust debate over a claim to riches. One, a storyteller type with wild gesticulations, insists he has seen a cave glittering with gold, but his companions suspect it’s nothing more than ale-inspired fantasy.

11) At a nearby vendor’s stall, simple candles appear amongst the goods, priced too good to be true. The merchant claims they are made with a magical formula, able to burn indefinitely. The prospect is alluring, but surely there’s a catch?

12) Dr. Robert, a self-proclaimed wizard of great repute, operates from a makeshift booth tucked away in a side street. He boasts a glittering elixir claimed to cure any malady. Desperate souls come with coins in hand, though skepticism looms about the potion’s veracity.

13) On the corner, a man displays copper charms fashioned into rat silhouettes, declaring they will ward off vermin. Locals glance with intrigue, pondering if superstition is worth the modest investment.

14) A smiling woman has set up tables laden with adorable kitten statuettes. They catch the light and the hearts of passersby, who can’t help but appreciate their craftsmanship.

15) An elderly man unrolls scrolls with a flourish, offering ancient wisdom at a price. But as he recites excerpts, which sound more like nonsensical ramblings, most scoff and carry on their way.

16) A merchant proffers tiny vials filled with a mysterious potent liquid, promising Herculean strength to those who imbibe it pre-endeavor. Some townsfolk seem tempted, but others question if it’s merely strong spirits in disguise.

17) At the center of a captivated crowd, an old crone weaves elaborate tales of legendary beasts that once clashed above and beneath where the city now sprawls. Her morbid prophecies of their return lend a chilling air, leaving some to wonder if there is truth in her words.

18) Another woman further down the street is hawking books, the covers bearing titles of the return from death’s embrace. While varied in authorship and era, they exude an eery consistency—tales of the dead reincarnate.

19) At a corner stands a man, boasting a detailed map to a mythical oasis beyond the craggy mountains. His confidence is enticing, his directions simple—follow the map to the letter for success. Adventure beckons for the hopeful.

20) A scuffle turns heads as a lone figure is set upon by thugs. Those who intervene find themselves embroiled in a battle against street toughs adamant about punishing the stranger.

21) A ragged street preacher imploringly asks for alms. When he receives a few coins, he dashes with unexpected vigor, vanishing as quickly as he appeared, leaving benefactors befuddled and lighter of coin.

22) The street performance captures attention with a troupe imitating a familiar band of adventurers—remarkably similar to the party. Chuckles and cheers abound as the escapades unfold, the flattery of imitation not lost on the actual heroes.

23) In the plaza, raucous laughter cascades from a play mocking the local lordship. The jests, however, draw the ire of the law, and as the constables approach, the party’s sense of justice is put to the test. Do they defend freedom of speech or avoid confrontation?

24) At the edge of civic unrest, angry voices chant for the ousting of a despot. Flames flicker in eyes seeking change, and the once peaceful street steels itself for a siege upon a tyrant’s residence.

25) Children animate the streets with cries of “Bandits and Raiders,” their excitement palpable as they scheme to plunder imaginary gold from the “lord’s vault.” What’s play to the children, however, could spark real trouble if misinterpreted.

26) As rumors of hidden dragons circulate, tavern talk turns speculative. Some claim a beast slumbers within the town’s plaza, others say it soars silently through the night sky, and more speak of cavernous lairs.

27) Yet the town’s most captivating tale speaks not of treasure or draconic myths, but of Alyana’s disappearance. Appan and Ehelda, her forlorn parents, weave through the crowd, their silvered visage bespeaking aristocracy in distress. Becoming rescuers could lead to a noble’s gratitude—or entwine the party in familial intrigue.

28) A band of battle-worn mercenaries pitches a contract; they seek respite in work, willing to lend steel and shield to the party’s endeavors for a just wage.

29) Theological arguments echo from a temple’s steps as two clerical factions spar over the righteousness of magic. One champions benevolence, the other power. Their discord poses a conundrum—does one school deserve the party’s aid?

30) Soldiers march with intent, tales of recent skirmishes trailing their boots. Yet, beneath the valorous veneer, disillusion ferments. Engage them in conversation, and a sobering narrative of conflict unfurls.

31) Marlon, a keen collector of discarded weaponries, boasts a robust collection of arms and armors scavenged from forsaken fortresses. His wares hold the allure of history, battles long fought and sieges weathered. They may not be the finest quality, but they carry a sense of nostalgia.

32) In a corner, a shoe vendor hawks her wears with a twist. Claiming herself as an elf in search of kin, she offers intricate stories of the far-flung Black Forest in exchange for silver-coins-and-a-pair-of-shoes deal.

33) A boisterous game of dice captivates a dingy alley as two men make sport of their fortunes, inviting passersby to try their luck on the roll of a dice.

34) A bustling trade in the street sees an array of peddlers from different lands. Oddities and trinkets abound, but a closer look reveals the not-so-convincing facade. Counterfeit silks, wines that taste more like vinegar, and rusty antiques add a dash of caution to the shopping spree.

35) Gerald, a local doodler turned cartographer, shows off his supposedly treasure-laden maps, more a product of imagination than exploration. A good draught of ale might loosen his imagination and the price.

36) Setting up their canvas for a grand show, a group of art merchants discuss the arrival of affluent patrons and the grand fortune they hope to amass.

37) An antique dealer sells an old mirror, hinting at its mystical property to show the past. For some, it’s a novelty; for others, it offers a tantalizing possibility of reliving bygone days.

38) A skin-and-bones man stands ranting at the intersection. Every now and then, he warns passing folks about the dire possibilities of goblin invasion from the sewers, his wild gestures and unsettling smirk making people question his sobriety.

39) A lost dog hunt proves oddly intriguing for the sizeable reward, pittance of copper pieces. But as the party investigates, they stumble upon a twist—it’s a mimic, mischief in the form of an innocent hound.

40) In another part of the town, a man’s drunken rambling about his brush with a vampire takes a serious tone when he implores someone to destroy the vampire’s remains. A tedious trip later, the party faces an unexpected predicament—the remains are of man’s deceased dog.

41) A missing ring sets a curious quest, a handsome sum drawing many seekers. Tales of an ape dancing around the town with a shiny piece appear ludicrous until the adventurers confront the ring-stealing primate.

42) A seemingly harmless game of children turns challenging as they lure adventurers into their make-believe “Bandits and Raiders” world. Suddenly, the stakes are real when thieves mistake the game for an actual heist plot independent of the kids.

43) Finally, in the city’s heart, a clamor against the government brews. A menagerie of the downtrodden prepares for an act of civil disobedience, the line of justice murky as the party must decide their alignment.

44) The whispers of a con artists’ group out to dupe the city under the disguise of doomsday prophets makes the rounds. Pious robes mask the deceitful hearts as they harness faux-divine powers to protect their ill-gotten wealth.

45) The same street bears witness to another chaos—an ape running amok, its captors struggling to control it. The uncanny amusement disintegrates rapidly into terror as their attempts go awry, pulling the party into the unexpected disaster.

46) A man famed for his crooked ways promises an exotic, rare sword carrying a supposed curse. A rich offer, a perilous gamble. Is the risk of being cursed by the blade worth the reward—only the party can decide.

47) An innocuous scene of halfling kids chased by seemingly villainous orcs takes a surprising turn as the orcs turn out to be playing along, the halfling kids screaming in delight rather than fear.

48) Deep beneath the hearty spirit of the city, an ominous undertone emerges as tales of slave traders run rampant. Wolves and lions being sold off as exotic meals or dangerous bodyguards cast a dark shadow on the city’s underbelly.

49) In the midst of an uproar, an argument between merchants unfurls that price-fixing cheap knock-offs could drain their competitors and monopolize the market, resulting in an unsettling power shift.

50) The city’s grand plaza lies in disarray—a group of children using a historic cat statue as their plaything. It’s all fun and games until a stricter, vindictive group of adults approach, leading to a confrontation—the party caught in the middle.

51) A street corner hosts an unfortunate drunkard belting out slurred songs about a hidden treasure. His claims are as questionable as his sobriety, yet they spark curiosity among the eavesdropping crowd.

52) A devout cleric approaches with religious fervor, eager to invite the party to a celebration at the local thieves’ guild—a rare occasion where mischief and reverence collide in harmonious camaraderie.

53) A melancholic vendor offers a selection of sweets that resemble rat skulls a little too closely for comfort. “Candied fruit, unique taste,” he claims, but one must wonder if there’s more to these treats than meets the eye.

54) A gathering of children becomes unruly as they pelt a statue with stones. Reprimanded by an adult, the game quickly ends as they scatter into the nooks of the city.

55) One merchant seems particularly keen on disposing of his stock, which includes a suit of +1 plate armor, or so he claims. Closer inspection reveals it to be an elaborate ruse crafted from paper-mache—a decoy for the unobservant buyer.

56) In a panic, another merchant frantically attempts to sell his stash of barrels before they start to leak, threatening to spoil whatever mysterious contents lie within.

57) A third merchant forms part of this chaotic tableau, determined to sell as many fake gold coins as he can before his deception is uncovered. The allure of gold is a strong one, but at what cost?

58) Amidst this bustling market, another merchant is hastily trying to sell bags of beans while shouting “Thieves!” at any who dare to approach his wares. Is this an elaborate distraction or a genuine plea for help?

59) A quaint game among children capturing the innocence of imagination—they entangle their fingers with strings, inviting unsuspecting adults to play along. The rules are simple; evade the traps, outwit your peers, and enjoy a hearty laugh.

60) The song of innocence turns into a cacophony as another group of children engage in a dangerous game, hurling stones at one another’s heads. A moment of childish fun, perilously close to causing real harm, puts the party’s intervention instincts to the test.

61) A group of youths sing a harmonic, yet scathing ballad about a local thieves’ guild, not realizing the potential wrath they might invoke from the unsavory characters they mock.

62) At the edge of paranoia, a man threatens the populace with apocalyptic visions of goblin forces emerging from the sewers. When he finally lunges forward to defend the city, it reveals itself as stage one of a campaign-spanning quest.

63) A row among merchants, all of whom accuse the other of treacherous dealings and market manipulation. Only time will tell if their collective finger-pointing will lead to an open brawl or mutual understanding.

64) In a peculiar show, residents attempt to glimpse their reflections in a large mirror. Vanity, or is there something more mystical at play? Dare the party peer into its depths and see what gazes back?

65) With a tone of cautionary fervor, a woman warns of the vampiric threat lurking in the sewers. But is she a harbinger of truth, or is her ‘quest’ merely the ramblings of a fantastical mind?

66) Breaking the city’s humdrum, a man’s frantic claims of ogres hiding in the sewage system adds a layer of excitement or perhaps unwarranted fear.

67) Treasure buried in a nearby dungeon sets the foundation for fierce debates over its whereabouts, as treasure hunters, scholars, and adventurers alike converge with maps and scrolls to dispute its true location.

68) Similarly fervent discussions about a different dungeon echo through the streets, a heady mix of confirmed facts and fanciful rumors blurring the lines between lore and reality.

69) In another curious spectacle, locals brandish a mirror in a vain attempt to capture elusive reflections—whether of strangers, friends, or otherworldly entities is anyone’s guess.

70) A cloaked figure appears, enigmatic in demeanor, selling an ostensibly majestic sword with an equally imposing curse—beware the blade that bites its master.

71) As a vivid tableau of creatures and curiosities paints the urban landscape, tales of a hidden dragon stir the collective imagination. Whether it slumbers in local caverns or brazenly prowls the skyline, the city abounds with whispered theories and potential quests.

72) In the midst of this mosaic of myth and market, Appan and Ehelda, elegantly attired, seek out the party with tales of their vanished daughter, Alyana. Could this be the prelude to an epic journey or a descent into a web of deception?

73) A ready collective of grizzled mercenaries searches for purpose among the cobblestones, offering their services to the highest bidder, or perhaps to kindred spirits in search of glory and gold.

74) At the temple’s foot, a schism of thought—magic and its moral compass become the crux of heated arguments between priests. Their divine dialectic beckons the party to weigh in on the ethical points of arcane practices.

75) Soldiers, fresh from the fray, shoulder tales of valor as easily as their battered shields. Yet beneath their storied scars lurks a truth untold—a battle’s glory is often overshadowed by the grim reality of combat’s aftermath.

76) A seasoned entrepreneur named Marlon, set up upon a temporary stall, peddles an assortment of artifacts—each a silent witness to history’s forgotten conflicts. These relics of yore carry the potential for greatness and the scent of past bloodshed.

77) A crafty shoe-seller, her eyes gleaming with sly intent, entices the party with footwear seemingly perfect for their journey. A few stories of elven woods and mysterious kin are part of the bargain, spun with the promise of guiding the weary traveler to wonders untold.

78) The rhythmic clatter of dice echoes against the walls of the city, where two enthusiastic gamblers seek companions to share in their game of chance. A roll here could mean easy coin or hard lessons in the fickle nature of fortune.

79) Merchants from distant lands unfurl their collections in a vibrant display of commerce. Hidden amongst the wares lies the challenge of discerning genuine treasures from well-crafted replicas designed to befuddle the unwary.

80) With a salesman’s charm and an ear for good gossip, Gerald invites onlookers to peruse his collection of hand-drawn maps. A sip of fine spirit might sway him to part with his creations—provided the tales accompanying them hold water.

81) Art merchants, with their swathes of canvas and brilliant pigments, set the stage for a day rich in color and commerce. For those astute enough to discern the strokes of a master from an amateur’s effort, investment in the right piece might yield returns beyond the canvas’s edge.

82) An elderly merchant’s pitch to sell a mirror of the past creates a ripple of interest. Whether he holds a relic of time or a well-polished looking glass is a question that tempts those with nostalgia or curiosity in their hearts.

83) Amid the town’s bustling activities, a man’s vehement warnings against the dangers lurking within the city’s sewage system strike an odd combination of anxiety and bemusement among his audience.

84) A desperate man—whiskered and wild-eyed—warns of vampiric remnants haunting the shadows below. His plea for a resolution is an enticement to delve into the darkness, for the satisfaction of ending a haunting or uncovering the truth behind fearsome whispers.

85) Ogres in the sewers? The raving claim from a corner prophet draws a murmur of fear and skepticism. Yet, if his words hold a grain of truth, courage and readiness could be the light that purges shadow from the depths.

86) A gruff blacksmith pounds away at his anvil and eagerly shows off his latest creation—a sword he claims can cut through the thickest armor. He offers a demonstration, slicing through a pile of metal scrap with ease.

87) A florist’s stall overflows with an array of exotic blooms, releasing intoxicating scents into the air. The florist claims that each flower has a unique property, from inducing sleep to acting as a love charm.

88) A man in tattered robes stands on a street corner, handing out pamphlets about an imminent doomsday. He speaks with such conviction that a few citizens stop to listen, entranced by his apocalyptic tales.

89) A troupe of acrobats performs breathtaking feats in the plaza, drawing a crowd of admirers. Amid their flips and spins, they surreptitiously pick pockets—a theft act hidden in plain sight.

90) A furrier displays pelts of unusual creatures, some shimmering with unnatural hues. He claims they’re from beasts of far-off lands, though skeptics whisper about magical tampering.

91) A cheery pie vendor claims her treats are baked with fruit from the enchanted orchards of the Feywild. She offers free samples, and patrons find themselves momentarily lost in euphoric taste sensations.

92) An improvised comedy troupe turns everyday squabbles into a side-splitting spectacle. Their spot-on improvisation and wit draw in titular donations from the amused crowd.

93) A stone-faced guard patrols near the town gate, wearing a plumed helmet much too large. When asked, he admits it’s a penalty for losing a bet with his captain—a reminder to stay solemn in his duties.

94) A collection of dolls, each intricately fashioned to resemble various city officials, can be found at a quiet stall. The dollmaker assures you that they’re just toys and definitely not for casting curses.

95) A hunched old man at a street crossing insists on telling fortunes for a copper piece. His predictions are vague but unnervingly accurate.

96) An exotic pet merchant presents a cage with a creature that looks like a cross between a cat and a lizard. He swears it can hunt down any vermin and even claims to eat small terrors in the night.

97) A woman keeps exclaiming about lost keys. When approached, she explains a riddle given to her by a fortune teller, implying that whoever solves it will open the door to great wealth.

98) An inviting aroma leads you to a food cart where a quarrelling couple throws ingredients into a pot, each claiming their recipe is superior. The result is a surprisingly delightful stew, creating quite the line.

99) Two jugglers toss flaming torches to each other with alarming casualness. They shout challenges to the growing audience, suggesting tasks for them to make the show even more thrilling—for a few silvers, of course.

100) A reputed palmist reads hands, his table overflowing with trinkets purported to enhance his sight. He holds an audience captive with revelations that seem too personal to be mere guesses.

Remember, if you want more RPG random city encounters, head over to Random Encounters AI, another website I built. Enjoy!

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!