Sooner or later, every adventuring party ends up returning to civilization. Continuing along with my series of random encounters, I am going to dive into the bustling streets of the city.

One of the biggest challenges to running towns or cities lies in being able to sell your players on the illusion that they are in a vibrant location with lots of activity and interesting people to meet. If one of the characters heads off to go shopping or another goes to visit the church, it can be helpful to have a little something ready for everyone else. This helps to keep everyone entertained but also fleshes out the city a bit.

These are all non-combat encounters (at least they start out that way) and most could be as mundane as can be. That said, I have tried to leave the door open for you to build on them as you see fit. You could easily use many of these as ways to introduce important new NPCs or plot threads within your campaign. These are merely intended to give you little hooks to work with.

That is enough out of me. When you find yourself in need of a little urban encounter, scroll through for something you like or roll a d100 and let the city unveil its secrets before you.

1-2. Mysterious Art Piece: A skilled artist showcases their wares, included a painting that is the spitting image of one of the party members. The character has never met the artist, so how did the piece come to be made? Was it mere coincidence or is there something more at work?

3-4. Unusual Street Vendor: An eccentric merchant peddles curious trinkets and unique items from a mobile cart. While likely mundane baubles, these wares may hold hidden magical properties, secrets, or serve as conversation starters. Might they be a source of information for some items the party recently acquired?

5-6. Graffiti Artist: A graffiti artist captures the party’s attention as she puts the finishing touches on a vibrant mural. Perhaps the artwork conveys a hidden message that is recognized by one of the party members. Alternatively, what will the party do if the city watch attempts to apprehend the artist?

7-8. Lost Pet: A distressed citizen seeks help in finding their beloved pet that has gone missing. The individual would surely be in the party’s debt if they help to return the lost creature. Perhaps the hunt will reveal a hidden side of the city.

9-10. Accused!: A stranger points out the party to the city watch and accuses them of a minor crime. Yes, the band could likely fight their way out but would it be worth being branded as criminals? Why were they accused in the first place and could the party end up benefitting from the situation?

11-12. Urchins: A band of street urchins approaches the party, begging for handouts. The waifs will be thankful for any help that they receive and could become valuable assets to the party in the future.

13-14. Street Performer: A talented bard captivates the crowd with a mesmerizing display of music or storytelling. As the party passes by, he encourages them to join with him in song or dance. Allow characters who oblige temporary bonuses to performance-based skills.

15-16. Wanted!: After making the acquaintance of a helpful stranger earlier in the day, the party sees a wanted poster bearing the likeness of the individual. How will the party respond? Do they seek out the fellow and ask for his side of the story or immediately run to the authorities?

17-18. Street Brawl: A heated dispute between rival factions erupts into a chaotic street brawl. The party can choose to intervene, support a side, or find a diplomatic solution to ease tensions and prevent further violence.

19-20. Secretive Exchange: A party member witnesses two suspicious figures engage in a clandestine meeting, exchanging cryptic messages. Observing or interfering in their dealings might lead the party down a path of intrigue and espionage.

21-22. Fortune Teller’s Prophecy: A fortune teller with a decorated tent beckons the party to unveil their future through palm reading or reading tea leaves. The predictions can provide valuable hints or create new plot threads.

23-24. Mysterious Puzzles: Characters with an appropriate background identify a series of cryptic riddles etched on city walls. These seem to challenge passersby to solve the puzzle. Unraveling the enigma may grant access to hidden locations, secret societies, or reveal a long-forgotten treasure.

25-26. Street Food Extravaganza: A vibrant street market lures the party with an array of tantalizing aromas and mouthwatering delicacies. Trying the exotic dishes may grant temporary benefits or lead to an unpleasant digestive issue. Perhaps the vendor hails from some exotic locale that the party wishes to know more about.

27-28. Crier’s Announcement: A town crier delivers an urgent message, revealing the arrival of a renowned figure. Paying attention to the announcement could open new opportunities for the party.

29-30. Busker Battle: Two competing street performers engage in a friendly rivalry, showcasing their talents in a captivating music or dance battle. The party members get dragged in to deciding on the winner. Taking sides or joining the performers might result in a memorable performance or unexpected rewards.

31-32. Fanatic: A follower of a fringe cult preaches what seems to be nonsense in the town square. However, as the party passes some of what the fanatic says starts to sound very familiar to the party. Do they shrug it off or attempt to question the individual further?

33-34. Lost Heirloom: A distraught citizen recounts the story of a stolen family heirloom and implores the party’s help in recovering it. The search could unravel a larger conspiracy or connect the party with influential individuals.

35-36. Drunken Celebration: The party witnesses another group of adventurers who are celebrating a successful campaign while quite inebriated. In their impaired state, is the group boisterous and looking for a fight? Perhaps they let slip a mention of some great treasure that they failed to recover?

37-38. Mysterious Street Merchant: A half-starved merchant sells bizarre and seemingly useless items. These seemingly worthless objects might hold hidden properties or serve as catalysts for unique quests and encounters. Is there some benefit if a party member takes pity on him?

39-40. Public Debate: Intellectuals or scholars engage in a spirited debate on a prominent topic that interests the party. Participating in the discussion may grant valuable knowledge or insight into ongoing events in the city. Alternately, it may show the party’s hand and allow nefarious individuals to know their stance.

41-42. Secret Meeting: A group of cloaked figures gathers in a secluded alleyway, exchanging hushed whispers and secretive glances. Eavesdropping or confronting them could reveal a conspiracy or lead the party into an unexpected alliance.

43-44. Wizard’s Apprentice: An aspiring young wizard performs tricks on the street. He is not terribly skilled but is clearly giving the performance his all. Assisting the apprentice may help to gain the favor of his patron, who may hold valuable information.

45-46. Fortune’s Wheel: A mysterious woman offers the party spin on her wheel of fortune  for a nominal cost. The outcome of their spin may grant them a boon, bestow a temporary curse, or open a pathway to unexpected encounters.

47-48. Eloquent Orator: A charismatic orator captivates a crowd with a powerful speech, stirring emotions and raising awareness about a pressing issue. Choosing to support their cause or challenge their beliefs can shape the city’s future.

49-50. Ghostly Haunting: The party encounters a ghostly apparition or lingering spirit seeking closure or assistance. Helping the ghost find peace may unravel a dark secret, lead to hidden treasures, or unveil forgotten history within the city.

51-52. Cryptic Street Art: An enigmatic piece of street art appears overnight, featuring symbols or cryptic messages that seem to defy interpretation. Deciphering its meaning may lead the party to a hidden location, a secret society, or a mysterious individual.

53-54. Hidden Resistance Movement: The party stumbles upon a covert resistance movement working against an oppressive regime or corrupt organization. Earning their trust and joining their cause could lead to a city-wide revolution.

55-56. Dragon Chess Master: A skilled dragon chess player sets up a public board, challenging passersby to a game. Defeating the master could earn the party member a seat at an underground tournament, with a special prize.

57-58. Illusionist’s Performance: An illusionist stages a breathtaking performance in a public square, showcasing mind-bending tricks and optical illusions. Knowledgeable party members can see through his illusions but he is passing them off to the gullible as being legitimate. Citizens are spending their hard-earned money, will the party intervene?

59-60. Local Celebrity Encounter: The party encounters a well-known figure from the city’s social scene, such as a famous actor or renowned author. Engaging with them could lead to unexpected opportunities or potential complications. What if he is not all he is cracked up to be?

61-62. Wishing Well: While passing by an ordinary looking well, one of the party members hears a voice saying, “Drop a coin and make a wish.” Was this some trick played by local youths or is there some enchantment to the well?

63-64. Bizarre Street Vendor Competition: Two eccentric street vendors engage in a whimsical competition, each trying to outdo the other with peculiar and exotic goods. The party can choose to assist one of the vendors or find creative uses for their extraordinary merchandise.

65-66. Mysterious Midnight Procession: The party stumbles upon a solemn and mysterious midnight procession, led by robed figures carrying cryptic symbols or sacred relics. Following the procession may lead to an ancient ritual or a secret gathering of cultists.

67-68. The Haunted Alley: An infamous alleyway is rumored to be haunted by a vengeful spirit or ghostly apparition. Exploring the haunted alley could unveil a tragic past, provide clues to a murder mystery, or even grant an unexpected boon.

69-70. Secret Underground Gambling Den: The party accidentally discovers a hidden entrance leading to an underground gambling den. High-stakes games of chance unfold all around them but there are a lot of shady characters. Participating in the games could lead to fortune or ruin.

71-72. Conspiracy Theorist: A passionate conspiracy theorist pulls aside one of the characters and shares their theories about secret societies or government cover-ups. Engaging with them might reveal kernels of truth or inspire the party to investigate further. Alternatively, he may be a total nut.

73-74. Urban Oasis: Amidst the concrete jungle, a gardener has created a stunning oasis of vibrant flowers, herbs, and foliage. Assisting the gardener in maintaining the sanctuary could unlock benefits or provide a valuable source for ingredients.

75-76. The Enigmatic Beggar: A seemingly destitute beggar possesses an uncanny knowledge of the city’s secrets. In exchange for simple acts of kindness, he will gladly share his knowledge with the party. Building a relationship with the beggar may unlock vital information or unexpected assistance.

77-78. Execution: A large crowd has gathered in the town square to witness a series of public executions. As the prisoners are marched through the crowd, the party realizes that one of the condemned is someone they know!

79-80. Pickpocket: While walking through a crowded square, a youth bumps into one of the party members in an obvious attempt at pickpocketing. Catching them red-handed, how will the party react? Do they turn the would-be thief over to the authorities? Could the young fellow become a valuable asset?

81-82. Foreigner: One of the party member notices a foreigner who is clearly new to the city. The poor soul can’t speak the language and appears confused. Will the party lend a hand? Perhaps this individual is from somewhere of interest to the party.

83-84. Underground Market: A stranger mistakes a simple gesture from the party to be a secret password. As a result, the party gains access to a hidden underground market where illegal goods and contraband are traded. Navigating the market may reveal rare items or lead to encounters with dangerous criminals.

85-86. Rats!: Some of the party members witness rats scrabbling over the wares of a local food vendor. Do they keep this knowledge to themselves, risk upsetting the vendor, or possibly help with the issue?

87-88. Noblewoman: A noblewoman and her retinue barge their way through the busy street. It is clear to the party that she views the townsfolk as being beneath her because her retainers roughly shove them out of the way. Does the party let this stand or do they stand up for the regular folks?

89-90. Wedding Objection: A wedding procession makes it way through the busiest part of the city. All is well until a spurned suitor and his family arrive to object. Things could become violent. Will the party intervene? What if they personally know one of the individuals?

91-92. Sculptor’s Commission: A renowned sculptor approaches one of the party members and asks them to model for their latest masterpiece. Participating in the project might lead to unexpected connections or lead to unexpected fame.

93-94. Afflicted Outcast: In a quiet corner of the city, the party comes across a secluded figure shrouded in tattered rags, clearly afflicted by disease. He piteously calls for aid. Will the party keep a safe distance or offer to help the poor soul?

95-96. Follower: One of the group notices that the party is being followed. The follower isn’t particularly stealthy but is persistent. Is it someone with an evil agenda or perhaps the hireling f a foe? Alternatively, it could be a fan of the party or someone looking for help.

97-98. Citywide Celebration: The entire city is swept up in a grand celebration for a local holiday. Apparently it is customary for outsiders to put on a little performance for the citizens. This could take the form r a song, dance, or story. Will the party participate when they are put on the spot or disappoint the crowd?

99-100. Wagon Wheel: A local farmer, visiting the city with his produce is having trouble. One of his wagon wheels has come off in a busy intersection. The party could easily ignore this but if they help, a farmer could be a handy friend to have.

Conclusion:

That will wrap up my 50 urban encounters. Most of these are simply intended to give you something to toss out to the group while some of the party members are engaged in another activity. Little shorts like this have always been useful for me, to help make my cities feel alive. If you happen to be using my suggestion of providing a Who’s Who for your campaign, be sure to jot down the names of any new NPCs you end up creating.

Do you have any standby tips or tricks for when you are running your characters through populated areas? If so, drop a comment below. I would love to hear what you do. That is all for now.

If you would like some more random lists, you may find them here.

If you would like to access my maps with plot hooks, you may find them here.

Have a great week. Good gaming!