In the deep corridors of the city, a pulse can be felt. It comes in chimes of great bell towers sounding across the sky, the thrum of machines in industrial factories, the hoofs of horses carrying carts of merchandise, and the murmur of voices on the streets. Civilization is a thriving ecosystem amidst hovels of stone, clay, cobble, and iron. Every walk of life, profession, and opportunity for something strange and interesting to stumble upon.
Over the course of the past few years, running Dungeons and Dragons and other tabletop RPGs in multiple urban settings, I’ve accumulated quite a list of potential encounters and happenings that are perfect for fantasy city environments.
And why not? The joy of running a game in a city-based setting is knowing how dense and deep your party’s opportunities are. Where a large map contains a wide berth of various discoveries, those same discoveries in an urban landscape can happen just around the corner. The depth of civilization creates countless possibilities for quirky, fated, and dramatic encounters that any table would find compelling. So, I’ve finally gathered these homebrewed encounters together, workshopped them, and placed them into one, big, epic d100 table!
Quick suggestions for this encounter table.
This city encounter table is open-ended for the needs of the campaign. Some of these options are simple observations, while others are full-on adventure prompts. Many will ask you to roll or choose further options, or answer questions on-the-spot.
As the game master, you are completely 100% emboldened to mesh the suggestions of this table into your campaign in the best way you see fit, whether to 1) heighten the stakes of the game, 2) provide context without derailing the current adventure, or 3) intentionally set the party on a new course.
Free download of this d100 Encounter Table!
Also, if you enjoy this encounter table, please feel free to download the PDF version of it at the Chaotican Writer Ko-Fi, or at Itch.io!
It is being provided as a “Pay What You Want” offering, and I would super appreciate any amount you would be willing to pitch in. Running a website, newsletter, and other channels takes time, passion, and effort, and please know that every amount is noticed, appreciated, and goes towards keeping this site (and the Dungeon Delve newsletter) running and providing awesome content to the TTRPG and writing communities!
Also, if you enjoy this d100 table...
… please check out WobbleRockets d100 Table: Things To Find In the Deep Dark Woods, perfects for romps through enchanted forests, gloomy swamps, and deep wilderness.
| d100 | City Encounters or Urban Sidequests |
| 1 | Neighborhood Cult A strange cult has been conducting processions in parts of this neighborhood late at night, and the locals are abuzz and fearful. Its easy for the party to overhear rumors as they pass. What’s even worse, someone who is a known member of the community has gone missing over the past few days. |
| 2 | Action News Reporter Scribe for the local herald is seeking the hot scoop on the party’s exploits, assuming they have already performed noteworthy deeds. They are following up on rumors and want firsthand accounts from the party, though the notes taken are a mixture of truths and falsehoods. Once the reporter has enough, they leave. The story will appear in tomorrows broadsheets, bulletin, or morning herald, sensationalizing the rumors and taking their quotes out of context. |
| 3 | A Chittering Surprise In an industrious area with multiple warehouses, local workers are approaching a large wagon filled with oak barrels, each labelled and carrying salt, flour, meat, whiskey, or other goods. In the midst of offloading, a foreman becomes suspicious and orders one over to have it opened and inspected. Upon doing so, not only are the goods missing, swarms of insects scramble out of the barrel and begin attacking everything in sight. |
| 4 | Street Dunk Inflated ball bounces towards one of the characters. A group of children approach, one betting they can’t put it through the tall hoop set up on the street corner. If they succeed, they get applause from the children. If they manage to do it with style, they become their favorite stranger for the day, and gain inspiration. |
| 5 | I Got A Deal For You A traveling salesperson in a wagon notices the party, stopping to offer them a free ride to their destination. The salesperson tells them about exciting investment opportunity. Choose or roll (1d6) one of the following: a new potion shop in another town, a series of autonomous carriages, a miraculous invention that teleports between two cities, a timeshare in an old castle, a tunic tailorship looking to sponsor, or a new “magic” currency. Roll or determine the likelihood of an all-out scam. |
| 6 | A Flying Omen An enormous creature flies overhead. Choose or roll (d10) one of the following creatures in their giant variant: dragon, griffon, wyvern, bird, insect, bat, tentacled aberration, fiend, celestial, winged mutant animal. How to those on the ground respond to this event? What could be the meaning of this? |
| 7 | Strange Envelope One of the characters steps on an envelope with a note inside which has been left on the street. Choose or roll (1d6) one of the following: a component list to a brand new spell and an address to deliver them to, a torn headline about recent occult murders in the city with co-ordinates scribbled in the corner, a strange incantation that summons an imp or other small fiend, an important missive for the leader of the watch with seal intact, a teleportation scroll swapping the character with a criminal behind bars upon reading, notes to an original song by a local bard with their signature in the corner. |
| 8 | Trail of Ancients At a busy sprawl of narrow streets, at an alcove between two buildings, a disheveled stone monument with giant runes stands with small weathered leaflets piled underneath. Each leaflet has the same runes marked upon it, but it seems whatever ceremony these were for happened weeks ago. If successfully transcribed, its determined that this is the first marker as part of the local pilgrimage of some unknown religion. A feint divine magic aura surrounds the runes. |
| 9 | Corrupt Shakedown Taking a shortcut, the party turns a corner into a nearly empty street to notice what appears to be a city watch patrol. Three armed and uniformed guards are interacting with a shop owner and a couple of locals nearby. The scene holds an air of discomfort. The leader, a sardonic fellow, notices the party and stops them, claiming this street is closed and they’ll have to go around. If they refuse, the officer requests papers and another raises to point a crossbow at the party. If the shop keep is questioned, they claim a burglary took place the night before. The two locals refuse to speak, visibly frightened. … Something about the situation doesn’t feel right. |
| 10 | That’s Not A Dragon (Eagle, Bee, etc.) A small two-person zeppelin floats several stories above the street. The ship-like vessel bears a banner of a small crate with wings, and the hot air balloon is in the shape and style of a recognizable flying creature. However, a trail of smoke can be spotted, as it appears the vessel has caught fire. One rider is waving a rug at the flames failing to put it out, while the engineer is peering down to the street, yelling for a couple buckets of water, lowering a rope with a hook. |
| 11 | 21 Rage Street A city watch unit has established a perimeter around a nearby stone-brick building, cautioning passersby from getting too close. Occasional sounds of thrashing can be heard from inside the door. One officer dabs a handkerchief across their forehead, clearly nervous. If questioned, they mention a rather large barbarian is in a fit of rage and they’re having a hell of a time trying to de-escalate the situation. What could the anger be about? |
| 12 | Oh Look! A Manhole Due to an obstruction in the path, or in avoiding a threat whose risk has increased throughout the day, the party has reached a dead-end where the only way to go forward is through the sewers. Proceed through the rest of the journey under the city streets, and either roll for a sewer-based combat encounter, or this table again revised for a sewer-based environment. |
| 13 | The Oathbreaker A powerful outsider descends from the sky in a fiery blaze, and makes a hard three-point landing in the middle of the street. This entity, whether celestial, infernal, or otherwise, is on a mission of retribution over an oath (or deal) being broken by someone nearby. Who is the oathbreaker? What oath did they break? |
| 14 | The Days Events A town crier or broadsheet seller is declaring the most recent news at the street corner. It is a mixture of tabloid news, including exaggerated claims about recent city threats, a scandal surrounding a celebrity or person of renown, and an upcoming festive event hosted by a small faction. |
| 15 | A Muddy Gift A small rodent brushes past as the party crosses a canal bridge. As it jumps into the water, a group of uniformed men rush onto the bridge, firing crossbows at the ripples the animal left in the water. While they curse and fire the last few missiles they have, one of the party members notices the animal left a muddy gem on the top of their shoe. |
| 16 | No Mas A protest march is happening in the path of the party. Choose or roll (d6) one of the following options; a crafting guild demanding policy change from the local magistrate, a group consisting of one or more ancestries are advocating against a new law marginalizing them further, a group of artists and musicians protesting a new ordinance suppressing works of a certain topic or nature, a union of laborers advocating for better wages, citizens advocating for the release of a falsely or negligently imprisoned figure, or an eclectic group advocating something innocent and silly. |
| 17 | Company Town Metal gates have been recently built in this path, and hired guards who are not city watch halt or redirect passersby. It seems that a local wealthy and corrupt magister had secured permit to gate the neighborhood. The party can do some haggling or bribing to get through the gates. If they do, they witness an impeccably clean and quiet neighborhood, though one of mixed unease and cold distrust of outsiders. Not to mention, entirely too many armed guards. |
| 18 | Thirsty Thursday Over the crest of a hill, a straight road stretches before the party, the near horizon dotted with a mixture of tavern entrances and stumbling patrons. The air is vibrant with noise, laughter, song, music, and the occasional glass breaking. Through a window, a series of people are gambling with cards, and some courtesans from a nearby brothel are conversing with eligible clients. It seems the party wandered into one of the more drink-friendly stretches of the city. Perhaps they party could fit in some carousing before continuing to their destination? |
| 19 | Pedal Pub Tour A pedal pub, the first of its kind! A burly and jovial bartender invites the party onto their pub on wheels, which moves by the use of pedals under the patrons feet while the driver pedals and steers. Two other travelers are riding along. Taking a historic scenic route, your party has time to get to know the strangers. One is a retired enforcer for a local faction, the other is a drunken pilgrim from out of town with a bizarre quest. |
| 20 | Tense Negotiations Two rival trade guilds clad in contrasting outfits bearing their respective emblems glare at each other from across the street. Tense negotiations are happening at a nearby tavern, and by the look in their eyes, a fight could break out at a moments notice. The city watch are cautious to get involved, but standing by a block away in case things get nasty. If the negotiation is interrupted by an adventurer, both leaders immediately accuse the other of paying the party to strong-arm the other. |
| 21 | Feeding Time A loud screech echoes from the distance. Multiple figures of giant flying birds (or other creatures) are seen approaching, as they swoop down and attempt to snatch panicked citizens. A few such creatures come down upon the party. If the fight serves difficult for them, one will call the others over (or take off with the citizens). |
| 22 | A Rookie Courier A young courier with a dark leather satchel rushes out onto the street and stops, their eyes resting on the party. Straightening their uniform, approach with an exaggerated stride. When close, they give greetings, announce their name and profession, and then salute (for a bit too long). In their satchel, they have a scroll for one of the party members. A summons, to be answered within a couple days. |
| 23 | Nobility Soap Opera Two esteemed individuals from separate houses, factions, guilds, or otherwise cross paths with each other, along with their armed escorts. There is an exchange of words between these individuals, indicating they are not the best of friends, and one subtly provides threat if the other proceeds on a current course of business. What is the tension about? What will this mean for the stability of the peace? |
| 24 | Its Just A Bowl of Soup A poor traveling cook has set up a makeshift fire pit and a rusty cauldron on the side of the street, offering soup for those who chip in coin to help them afford a stay here in the city. Depending on the neighborhood, the action is either an unlawful violation of city code, or is lawful but at the distaste of the sheriff or magistrate. |
| 25 | On Campus In this ward, lanterns are replaced with floating brass sconces with magical flames that shift in color, from cyan, to magenta, to gold. The casuals seem to be of a scholarly sort, clothed in linens, sigiled robes, and exotic fabrics. Elderly gents have an audible debate near the entrance of a school adorned with majestic columns and colorful banners. Some students pass a magical ball between one another with their feet for amusement. One solitary student is moving from person to person, trying to gather signatures for a petition. |
| 26 | Memory Lapse The party realizes they are at their destination. No once remembers anything about the journey; they only thing they know is that someone has a black eye, another has a cut across their arm, and a third has something in their pocket; a note that says. “Sorry for the confusion. A little something for your troubles.” |
| 27 | Flower Pot Disturbance A married couple are engaging in a spat over a recent cheating, and are taking their fight out on the open street. Others around the area have make a wide berth, almost as if they’re familiar with this couple and are aware of what could happen. The locals have secretly had enough of their chaos, as they’ve been cheating and getting back together for years. To make matters worse, one throws a flower pot at the other, and hits a character instead. |
| 28 | Burning Down A brick three-story building is on fire, and residents are trapped inside. The street is filled with panic as the local citizens are struggling to put the fire out with water from the local well. A novice mage is attempting assist, and has succeeded in freeing some of the trapped, but the fire is getting worse and their magic doesn’t seem to be enough. There is a yell for help from the third floor window. |
| 29 | The Hero They Needed In an alley, the party happens upon a costumed hero with a cape, having just swooped down to break up a bunch of thugs ganging up on poor bystanders. Their fighting style is highly acrobatic, and well trained, nearly fighting off the whole gang by themselves, with some struggle and taking of nasty blows. If the party helps them take out the trash, perhaps they may help them out in a future battle. … Furthermore, the hero speaks in a grim voice, and is prone to monologue themselves in the third person. |
| 30 | More Than They Appear A wandering priest with blank eyes and long white hair is drifting from person to person asking for charitable donations for the local temple of their peaceful nature deity. While hard of seeing, the humble priest does not forget a presence, and has more influence in the local neighborhood than they let on. Those who donate receive a blessing. A large donation will earn a favor in an unexpected place, though the party may not know about it until it takes place. |
| 31 | Pay It Forward A destitute beggar approaches asking for a bit of coin to afford bread. If provided either, they will share information about the area ahead that is useful for the party. Roll this encounter table again, but gain an advantage on the next situation. If none is provided, they will be caught stealing food later. |
| 32 | Chance Composition A bard is walking down the street with little notice to their surroundings, busy in their writing of a poem or song as they hum along. They recite part of the poem out loud, a phrase about the troubling times in the city and its outlook. Stumped at a particular line, they manage to poll a character for some help. If they do, the bard agrees to make that character co-author in the piece. The piece ends up in the broadsheets or bulletin, and becomes part of that characters reputation going forward, for better or worse. |
| 33 | Rent-A-Watch Due to low enlistment, the city watch is screening for volunteers in a booth at a city corner. They are seeking individuals with an enforcement or martial background, while remaining cautious about mercenaries or troublemakers. Otherwise, they are offering a quick training course, along with minimum of one day of service, an honorary service badge for good performance, and a days wage. |
Looking to receive updates on NEW articles, NEW resources, and NEW random name generators from Chaotican Writer? Subscribe to DUNGEON DELVE, the weekly newsletter and get a FREE 11-page Fantasy NPC Generator PDF!
| 34 | Illusory Swindle A signpost has something strange written on it. One of the arrows pointing toward an establishment has indecipherable script. If an astute and curious person attempts to understand it, that person will no longer speak common, and be forced to speak in strange tongues. If they approach the building the arrow points towards, they will find an eccentric an shady merchant who offers to fix their malady for a price, while attempting to swindle them for other services. While the swindler claims it could last a lifetime, the effect lasts for 24 hours and goes away on its own. |
| 35 | Street Sweep Due to the city’s most recent troubles, tending to facilities in the city had fallen behind. An overflowed sewer grate stirs an awful scent which travelers avoid by navigating elsewhere. A shop owner mentions they wish someone would take care of the mess as it’s driving customers away. If it is cleaned up, the owner gives a voucher for a 15% discount. |
| 36 | Not Just Parlor Tricks A charismatic street magician with a peculiar tattoo strikes up a conversation with the party, performing simple parlor tricks with a flair for performance. However, a scream is heard, and someone nearby collapses to the ground. While a crowd gathers, the “magician” slips away in the confusion. Upon investigation, the victim was killed by poisoning. Was the magician involved? |
| 37 | Prison Caravan A small caravan of armed soldiers guarding a prisoner transport passes by the party. On passing, one of the inmates peers out the barred window on the side, directly at the party. What about the party, or a character, has their attention? … Optionally, as the transport passes a block away, an explosion is heard. The wagon is toppled, and the prisoners are escaping. |
| 38 | The Spirit Shroud A thick fog has made traversing the city difficult, threatening to derail the party from their current journey. The nature of this fog seems just a bit more than a natural occurrence, as subtle silhouettes of incorporeal passersby form and vanish intermittently. Choose one of the following two options: add this strange complication to their destination, or reroll the encounter table as the party fails to traverse the streets and find themselves in another part of the city. |
| 39 | Tentacle Trouble A magic portal opens nearby. A wizardly individual with a deep blue robe drenched in water stumbles out, frazzled and gasping for breath. Moments later, a series of tentacles reach out of the portal, and attempt to pull the stranger back in while they do their best to fend off the monster. Those unlucky to be too close also risk being grappled and pulled in. |
| 40 | A Dead Body As the party winds through a series of side-streets, they turn the corner and happen upon a corpse lying on the ground. It is obvious from first notice that the individual did not die of natural causes, and their expression is one of shock. What caused the death of this individual? What clues lie nearby? Does the party decide to investigate? … and if not, how does this event ripple throughout the journey later? |
| 41 | My Baby! Yells can be heard from a nearby street. Those standing near hear sounds of a baby crying and a woman shouting about their baby being taken. Any who rush forward to assist will turn the corner and be met with an empty alley. Its an ambush! … However, if ignored or distrusted, the party will be visited late in the night by thugs dressed as city watch claiming the party was nearby and ask they step outside as they make a second attempt. |
| 42 | Meteorite Mayhem A fiery object falls from the sky, and crashes down a number of blocks away. If investigated, the party notices a chaotic scene. The block is filled with frightened locals. The top of a nearby building has been damaged, and rubble lies where a few shop stalls once stood. A few people have been severely injured and are lying on the ground. Finally, at the center of the street, they notice a smoldering crater with a glowing green rock at its center. |
| 43 | A Secret Shrine A narrow route through a twisting alleyway appears as a likely shortcut to the party’s destination. While navigating the busy corridor, a wrong corner is turned, and the party happens upon a makeshift shrine nesting at one of the dead-ends. The shrine consists of lit purple candles, strange-scented incense, a large rare feather, a small stone bust of a faceless horned figure, and an amulet with a red spinel gem. A silent cloaked individual is nearby, sweeping the alleyway with a broom. |
| 44 | Hung Out to Dry A hanging cage in a small town square contains a lone adventurer. The watch claim they are guilty of a heinous crime, but the prisoner claims innocence and wants the opportunity to prove innocence and get revenge on those who wronged them. |
| 45 | Snowcone Snafu A gnome tinkerer is demonstrating their new machine; a wheeled contraption that makes snowcones. This is part of an attempt to advertise their new business in town. However, shortly thereafter, the contraption begins malfunctioning. |
| 46 | Lady of the Doves A black dressed woman is sitting on a bench throwing seeds to rock doves, joining in with their coos. As the party passes, she bestows sage advice; the kind which seems a little too related to the party’s current goals. Who is this woman? Wait… where did she go? |
| 47 | Hungry Tome A traveling rare book merchant is selling their wares from a wagon. A particular book slips out in front of a character; an old philosophical tome with a mind of its own. Its looking for a new owner. And it hungers for knowledge. |
| 48 | I Know That Person A wanted poster hangs from a bulletin, bearing the likeness of someone of whom the party knows or has met recently on their travels. This comes as a shock, as the individual seemed pleasant and charming enough. This has to be a mistake (Or is it?). Roll a die to determine the severity of the crimes. |
| 49 | Rocks Underneath A small tremor knocks over loose various objects as the party passes. Fruit roll from stalls, pots fall from window sills, people stumble. Normal conversation says that these tremors have been happening intermittently in different parts of the area, but deep rumor suggests that a series of explosive battles underground are taking place, and that its even forced some creatures towards the surface. |
| 50 | Danger Is My Middle Name A gathering lies in the path of the party where a stage has been erected. Acrobats in festive attire are performing impressive acts of dexterity, juggling dangerous items while sitting on the shoulders of others who are having a light fencing match while another on a tight rope spinning fiery polearms passes above. Once finished, applause sounds, in which the charismatic leader in a jester hat riles up the crowd, and asks for a volunteer while spinning a large knife in their hands. |
| 51 | Rooftop Grove A druid who is in charge of a one-of-a-kind rooftop grove inhabited by earthen golems is distributing fresh fruits and vegetables to the most needy in the community via a couple pulley systems down to the street. The druid calls out a character to deliver a box of food to one of the neighbors. There is no expectation of payment in return, but it may afford a favor to the party later. Its good to know there are people in the community who know how to help out their own. |
| 52 | Wild Potions A traveling potion merchant with a festive hat and a large satchel approaches the party. Fast-talking and overly friendly, they attempt to convince to the adventuring party to purchase some of their wares. Many of the potions they have are unlabeled, and are in strangely shaped bottles, so only the merchant can tell what may be in them, and even this may be misleading. Once locked into conversation with the party, they refuse to leave until they purchase at least two or three items. |
| 53 | Renown and Ransom A canvasser wearing the colors or emblem of a local noble or aristocrat is moving from block to block, posting flyers with information about a recently missing person; a child or relative of the noble. |
| 54 | The Candymaker Can A colorfully clothed candy-maker is providing samples of their treats to passersby. If inquired by the party, they might be inclined to have a character test some “experimental” confectionary which they have created using exotic ingredients. If ingested, the effects are latent. In a couple hours, those who ingested the candy will be subject to a random effect from a wild magic table. |
| 55 | Delegate Caravan A small caravan transporting a delegation from a neighboring town, city, kingdom, or nation is passing through the street, escorted by armored soldiers on horseback. Choose or roll (1d4) one or more of the following: a simple opportunity to introduce a new NPC or world lore, the caravan stops at a shop as the emissary wants a special item or service performed, a lone anarchist throws an incendiary bomb at the main carriage, crowds of people are booing and throwing objects at the caravan. |
| 56 | Bakers Dozen As the party passes the bakers quarter, the aroma of baked goods fills the air. A number of small buildings staffed by caterers of various breads, muffins and other goods mingle beside other quirky shopfronts. One offers gourmet goods which provide a heightened sense of inspiration for those who partake, and who knows? Purchasing and offering one may help incur good terms with a stranger on their journey in the future. Meanwhile, another shop is not what it seems, and is in fact the front for a local gang. |
| 57 | Greedy Gamble Two nobles are in a betting mood, and someone in the party is their target. One thinks the person will perform a task, the other thinks they’ll reject it. They approach, and offer to pay a party member a substantial amount of gold if they perform an illegal act, uncharacteristic of them, or something risking of their life and limb. If attempted, the loser becomes petty and refuses to provide the money unless pressured. |
| 58 | Depressed Thief A goblinoid thief tries to stick up the party. However, they quickly become discouraged and begun sulking in a depressed state. If inquired, the thief confesses that its no use, and they will never get out from under their boss who they owe a large amount of money to… Unless the characters can confront he boss and either kill them, or get the thief off the hook. If they do so, the goblinoid joins the party and refuses to leave. Even if rejected, they’ll be found sleeping at the foot of one of their beds the next time they rest. |
| 59 | I Need Your Protection A stranger approaches the party, requesting protection and escort and is willing to pay. Choose or roll (d8) one of the following options; a noble whose escort has abandoned them, a vulnerable victim trying to avoid a stalker, a minor crime boss trying to avoid the law, a scholar looking for protection in a seedy part of town, an arcanist taking a shortcut through another plane, a son or daughter at the request of a parent whose family is the target of a vendetta, a courier who is carrying a highly secret message or item to the local magistrate, or a prisoner caravan whose escort is in need of support. |
| 60 | Rogue Warning A watchful individual is leaning against the wall near the entrance of an alley. If a roguish character is present, the person slips their ring past their finger knuckle and back as a sign. Provided that character is from the greater region, they understand it as a gesture signaling gang territory, and that the party should either avoid the area, or keep their eyes on their moneybags. Is this person a friendly acquaintance, or a threatening one? In either case, if they are approached, they will slip into the alley and disappear. |
| 61 | The Showmaker Canvassers in slacks and colorful vests with roses on the lapel are seen passing out flyers to an underground magic show later in the evening. The show is located in a building that was thought to be long abandoned. Unbeknownst to the party, the showmaker is not quite of this world. And they have business here which requires an audience. |
| 62 | A Matter of Possession An argument is taking place nearby between a man with a rolling pin in hand, and a darkly clad woman with her arms crossed. A third figure with a couriers outfit is standing next to them. Upon closer inspection, the woman is a necromancer, the man is a local chef, and the third is his undead brother. The matter of the argument; rights over the brothers body. |
| 63 | Small Dragon Fort The city watch has established a perimeter, as it seems a young dragon has made its home in a large pile of furniture, carts, and other small structures. If approached by a stranger, the dragon lashes out. However, if some method of communication or friendliness is established, it become apparent that this confused young dragon is a lost and frightened, and has created a “fort” with a small horde of items to feel safe. |
| 64 | Haggling and Hacking A thick scent of a rare spice is in the air as a small market of exotic trade goods lies before the party. Colorful banners hang from each stall, which carry an assortment of cages with small exotic animals, oddly shaped fruits and veggies, various colors of dye, and other sundry items. An overly eager merchant sprays a member with strange cologne, triggering an allergic reaction which lasts the entire day. |
| 65 | The Alley Cat A woman with frazzled hair marches into a nearby house, yelling at someone within. A young voice inside replies “Yes mother!”. Meanwhile, a floor up, the party notices someone slipping out of the second story window. Someone the party knows, OR a notable person who the party wouldn’t think. |
| 66 | Juggling and Jostling An eclectic band of entertainers have gathered a crowd on the corner. These jugglers, fire dancers, drummers, and various acrobats are putting on quite a show! When the party approaches, one of the characters is pulled into the fun, becoming the center of attention and gaining whoops and hollars. Once completed, the character is returned to the crowd inspired, … but missing an item. |
Chaotican Writer and Dungeon Delve are independent and lightly-ad supported, but there’s a ton more that goes into maintaining and delivering your favorite content! … Consider supporting via Ko-Fi!! <3 <3 <3
| 67 | Day at the Spa A cloaked individual steps into a wall mysteriously. If noticed and investigated, the party will realize it is the entrance to a secret spa located in a pocket dimension, ran by fay creatures. The party’s attention on the current quest is distracted, and whist forgetting what they were doing, may be tempted to bathe and rest at the spa instead. If the party consents, the fay queen refuses to let them leave until she has extracted information, dreams, or memories from them in payment. |
| 68 | From Out of Town Oddly-dressed travelers from a far-away region have only just arrived to the city, and are asking passersby for directions. Their presence is one of exploration and discovery, through its not immediately apparent whether this is their final destination. If the party assists them, the travelers converse with the party, and share a combination of lore about the region they are from, what they’re hoping to seek on their journey, and provide information on a place of interest in the wilds or another city that they stumbled upon. |
| 69 | Stone Cold Passing through a city park, the party notices a statue in the park seems quite realistic. It looks impeccable, as if it was chiseled out of stone yesterday. If the characters detect magic, they notice an aura. Upon an investigation, they realize it’s actually a petrified adventurer. What monster did this? |
| 70 | Cart Needs Help An overturned cart is causing gridlock at a busy intersection. The ones transporting the cart are busy trying to gather the items that have fallen onto the street. Those in the path are more concerned with complaining than helping. A simple, yet ridiculous situation to be certain. |
| 71 | Fencing In The Alley A handful of passersby are stepping into an alleyway with haste. If investigated, the party encounters a bald-headed rhyming peddler with a nervous tick parked with a cart and selling expensive goods for a fraction of the price. The cart bears a coat of arms, is clearly stolen, and the goods are going fast. In the middle of a purchase, someone shouts that guards are coming. |
| 72 | A Matter of Territory A large dead and skinned wilderness animal is hanging in front of a storefront or park gate. This gruesome display comes with a tribal symbol branded into the side of the creatures torso. If a rogue or barbarian is with the party, they may identify this as a warning that a dangerous gang or clan is moving into the area, and has marked this neighborhood as their territory. |
| 73 | Rush For Goods At an extremely crowded intersection of narrow streets, a dense market has sprung up in the party’s path with several vendors selling goods, bards playing music, and other loud activities. It is a veritable zoo of people. One merchant shouts loudly offering remaining wares for half price, and a sudden surge of people push through where the party is standing. All party members are at risk for either getting trampled or routed, along with the presence of a muddy puddle, a large pile of horse manure, a rather large brute with new boots. |
| 74 | Meet the Champion A famous athlete or fighter wearing flashy and extravagant clothing is crossing the street, a group of excited fans clamoring to get their autograph. They are on their way to train and prepare for the prize fight later in the evening. However, further down the road, a man in a cart full of crates is driving at reckless speed, and it appears they are on a collision course with the athlete. |
| 75 | Builders and Blunders A jet of steam shoots out of an exhaust pipe of a wheeled automaton that passes you, driven by a grizzled looking gnome, carrying a load of materials. Multiple laborers are loading and offloading crates of items, bundles of lumber, and metal rods. A dwarvish foreman yells out everyone to get a move on, and begins looking at a set of blueprints. Looks like the party has stepped onto a construction site by the local builders guild. What they are building? And why is that rope pulley holding up a plank supplies look like its about to break? |
| 76 | An (Un)Friendly Ride A carriage pulls over and a stranger in the back offers the party a free ride to their destination. The stranger has a scar across their left eye, contrasted with a cordial demeanor, and is accompanied by a large and silent bodyguard. If one or more party members accept, the stranger reveals in transit that they are an agent of a local faction (thieves guild, noble house, resistance, etc.). Aware of the recent exploits of the party, they wish to buy them off to betray their most recent quest giver. Otherwise, they give a veiled threat. |
| 77 | Magical Mishap A local wizards experimentation has gone wrong. Choose the effect; small animals become giant size and begin attacking the locals, or a single storm cloud passes triggering a wild magic effect, or the wizard themselves has become translucent and needs assistance before they disappear entirely. |
| 78 | Checkpoint Chance A security checkpoint has been established by the city watch, likely as a result of a current crisis in the city. Choose one of the following options; a typical security check with an opportunity to gain important information, a random interrogation over suspicions about potential involvement with a criminal event, or a illegal shakedown requiring a bribe to pass. |
| 79 | Wanted Poster A wanted poster bears the face of an unknown individual. Roll a d8 to determine who this individual is; a bandit leader, faction agent, cult leader, murderer, a pair of iconic bandits, a fallen paladin, a manic alchemist, or a rogue wizard. The bounty is posted, and demanding retrieval of a key item in their possession . |
| 80 | Peaceful Exorcism A band of ghosts are being directed by a group of chanting clerics in blue robes with brass hanging censors toward a nearby shrine from a large abandoned structure. The public is astonished, but the clerics assure them of this strange but peaceful exorcism. If interrupted, one of the ghosts flees to haunt a building the party shall enter later. Otherwise, the abandoned building is soon to be demolished, and there may be hidden possessions still inside. |
| 81 | Faction Violence An explosion rocks a storefront as a body of people engage in a violent brawl. Two opposing groups are taking their rage out on each-other, and it appears a number of injuries and some property destruction has already taken place. Review the various factions of the city, including city watch, noble houses, gangs, military orders, guilds, religious fanatics, political movement, and more. Roll to determine which two factions are fighting each-other, and roll to determine who appears to be winning. The party may deal with, or avoid the situation as they see fit. |
| 82 | A Delightful Melody A talented musician is busking on the street corner with a jar for tips. Anyone who donates a tip is provided a small melodic thank you. The highest tipper is offered to hear a sample of the musicians latest song If accepted, the character is momentarily entranced, and granted inspiration. |
| 83 | Calvary Collision A calvary officer in knightly armor is chasing a large animal on-foot, clicking their tongue and trying to compel their steed to come back. Stumbling on a gap in the stone road, the officer collides with a shop stall, damaging the display and spilling its contents all over the ground. As the merchant stands in surprise, and the animal trots away, the officer lies on the ground dazed. |
| 84 | Day at the Bathhouse A well-known bathhouse is advertising a day of free admittance for first timers to the establishment. If taken up on the opportunity, the party can spend some time refreshing themselves before they reach their next destination. That, or the party can roll another encounter, which is remixed to happen inside the bathhouse instead. |
| 85 | Noble Brats A band of pilgrims to the local temple lead by a pacifist preaching the rejection of material wealth are being jeered at, and having stones thrown at them by a group of young miscreants dressed in fancy coats. The youths are the children of a noble who has a disdain for their “pathetic” religion. Any disruption to the youths fun will attract the ire of the family. |
| 86 | Roll for Hilarity A slick of slippery or sticky liquid has spilled onto the street ahead, unbeknownst to the party. If anyone stumbles into the mess, they are in for a humorous, clumsy, and humiliating few minutes. To make matters worse, a group of laborers are sitting off the street nearby enjoying their meal, and will loudly welcome the entertainment while laughing at the unfortunate passersby. |
| 87 | Voice in the Well A stone well rests in the party’s path, As they pass, a young voice speaks out from within the well, begging someone for help. It is too dark and too deep inside of the well to see. Whatever it is, it is not what it seems. |
| 88 | Bridge is Out The bridge ahead appears to have collapsed down its center some time ago. Depending upon the setting of the city, it is constructed over a deep gorge, a shallow muddy channel to assist with flooding, or another hazardous gap. The characters will need to solve their way to cross, either by leaping, flight, a large object across the gap, or they may need to climb down and suffer the risk jagged rocks or diseased critters. If refused, the journey is delayed, and any events at their destination progress while they arrive late. |
| 89 | Taking Out the Laundry In a narrow street, a series of common clothes hanging across cords crossing between buildings on the upper floors. As the party moves forward, an overt group of thugs saunter into their path. One of them bears a bludgeoning weapon and spits on the ground, while the face of the group steps forward with a grin, feigning a courteous demeanor. They state that a nameless benefactor has asked their fine group of professional vagabonds to “take care of them”. No city watch appears to be in sight. |
| 90 | Trouble is A-Soot! A burst of smoke shoots out of a chimney nearby. At first, it looks benign, until another cloud billows and out crawl multiple creatures from the depths of the chimney, sprouting batlike wings and flying around the stack. Breaking formation, the smoke mephits swoop down to the street with a trail of smog, and begin causing havoc, breaking into windows, and attacking passersby. |
| 91 | Suffering Refugees A group of poor refugees huddle together. The atmosphere around them is one of suffering and loss. They speak of their homeland, their lives before the recent troubles, and the current state of things. Some have lost relatives, and those they care about. Where are these refugees from? What happened to their homeland that brought them here? What information can they provide to the party about the affairs of the world at large? |
| 92 | A Rival Party A small group of mercenaries saunter down this street, an air of conceit and ruthlessness accompanying them. A couple push aside passersby who stray too close, while another snatches food from a stall and bites into it without paying. This band is lead by a large individual with an officers uniform and several menacing tattoos. When one notices the party, they all quickly take notice, and begin sizing up the party as they pass. Whoever this group is, they’re sure to be trouble for the remainder of the party’s stay. |
| 93 | Bank Robbery Alarm bells ring inside a nearby brick building which holds a bank or jewelry store. A band of masked kobolds burst out of the windows or doors, making off with bags of goods. As they jump into the getaway carriage and take off, the party notices unattended horses. |
| 94 | Invite Only A hooded figure slips by one of the party members, sliding a small note into their pocket. It is a special invitation provided to individuals of “potential” and their party. Choose one of the following event options; a secret thieves market that deals with stolen and smuggled goods, an illegal gladiatorial combat event attended by the biggest names in the underground, a secret masquerade organized by a cabal of masked attendees. |
| 95 | Torrential Tower A strange micro-climate has sprung up in front of the party, consisting of severe weather that obstructs their view and slows their ability to move while possibly damaging them. People are rushing to get indoors. Above them, a small tower with top shaped like that of a witches hat hovers over the neighborhood. One of the locals yell at the party to get off the street. If inquired, they reveal that this has been a recent and common occurrence, and the residents are sick of it. |
| 96 | Ghost in the Machine A clocktower nearby strikes the hour, its ring resounding above the heads of the party. The most arcane-adept will feel a boom of thunder wash over them. However, the face of the tower is in disrepair and not moving. No pedestrian seems to hear it, claiming it’s been abandoned for years. |
| 97 | Mistaken Identity An aristocratic gentleman dressed in a dapper button-up coat approaches in a fit of glee to shake the party’s hands. They offer thanks for protecting him from a bandit ambush a week ago, including helping with a “personal favor” with a wink. Clearly mistaking yours for a different party, he invites yours to a ball this evening, where the real adventurers will later show up uninvited. However, if he’s corrected, he will apologize and appear later to hire your party for protection when those adventurers extort him for money. |
| 98 | Newcomer Finds Trouble A newly arrived traveler of a culture and ancestry uncommon in these parts. They appear to be at peak curiosity, wandering the streets, studying little peculiarities of the city, and taking everything in. As they stand out, they attract some curious or cautious attention. Who is this individual? Are they alone, or part of a group who arrived as well? What brings them here to the city? … But more pressing, who are the band of bumbling locals now approaching the traveler with a wolfs glare in their eyes? … This could get ugly. |
| 99 | We Have A Tail Someone seems to be tailing the party. They aren’t very stealthy, but they are persistent. Do they have bad intentions? Roll a die to determine their stance against the party, friendly or hostile. Roll another dice to determine their loyalty to one of a few factions in town. Otherwise, this person is just a courier concealing a small package; a gift from an unknown benefactor. |
| 100 | Clairvoyant Insight A doomsayer wearing a hat with a wide brim stands at the corner, shouting and warning all about signs from above and evils from below. The rising and mesmerizing tone of their voice attracts small crowds of people, who then scoff and leave. Upon the party passing, the individual peers directly upon a party member as if into their soul. They approach, claiming clairvoyant powers, and warn them of an evil on their path. While truthful enough, their description is infernal, darkly metaphoric, and highly exaggerated. |
HEADER IMAGE CREDITs: Aerial Shot of City Buildings by Pat Whelen
“Oh. How wonderful random encounter tables are! So may… pawsibilities!! … If you are seeking other resources for your Dungeons and Dragons, Pathfinder, or fantasy TTRPG campaign, why not check some of these other links below?“
- 5 Awesome Fantasy Map-Making Tools on Steam
- Unleash Your Imagination: Download our Fantasy NPC Generator
- Six Deadly Traps for Dungeons and Dragons/Pathfinder!
And dont forget to subscribe to Dungeon Delve, the weekly newsletter! Ta-ta!
Lead Writer/Editor at ChaoticanWriter
Avid geek, amateur historian, long time tabletop game master, content creator, and storytelling enthusiast. Matthew is a Augsburg University grad with a focused passion on fantastical storyworlds. He is also a musician, improv actor, live streamer, and proud favorite uncle. If you would like to know more, contact him, OR follow him on social media!
Latest posts by Matthew A Olson (see all)
- d100 City Encounters and Urban Sidequests - April 26, 2025
- Dirtbags! a Sci-Fi Shooter RPG: Gameplay Review! - March 23, 2025
- Nerds and Knights: a TTRPG “Nerd Nite” Presentation - February 28, 2025
