60+ Random D&D City Encounters, Medieval City Set Against Rolling Hills

D&D 5e Fantasy City Encounters

Many Game Masters and players tend to think of cities in Dungeons & Dragons as safe places. But, large places of civilization often abound with daily encounters, be them for good or bad.
Part of making a city feel alive in your D&D 5e game is the potential of running into something unexpected, something which makes the city seem like a dynamic ecosystem involving its people.

So, I’ve put together four 3d6 lists of random D&D city encounters for you to use in your game! Each list is separated out by the Tiers of Play, you have options for every level.
All I ask is, if you use these city encounters, please let me know either in the comments or tag my on Twitter @RolePlayRespite!
Be sure to check out my other random encounters as well as my D&D plot hooks for more inspiration for your game!

Without further ado, here are over 60 random D&D city encounters for you to use!

D&D City Encounters: Tier 1 (1st-4th Levels)

  1. An Owlbear (or a pair of them, if you think your players can handle it) rampage through the market. The creature was being sold as exotic pets to a noble house but broke free of their containment. Either way, the noble is angry they escaped (and potentially killed).

  2. Several pieces of outdoor furniture animate and begin accosting the city folk, including the player characters. Use the rules in the animate objects spell to determine stats.
  3. Several Giant Centipedes crawl out of sewer drains and begin attacking the city folk.
  4. A band of ruffians (use the Bandi stat block) surround the party asking for a toll to use their street.
  5. A small group of guards start harassing the party claiming they need to pay a tax for using the street they’re on. They’re not overtly threatening violence, but they seem eager to use their weapons.
  6. Someone bumps into one of the player characters at a full sprint. They hand something mundane over to the character, asks them to hide it and not tell anyone about it, and promptly runs off a side alley. Shortly after, a small group of guards jogs in the direction of the party, asking if they’ve seen a thief pass by.
  7. A fight breaks out between two groups of drunks. Some of the participants try to rope the party into the brawl.
  8. A haughty noble crosses paths with the party demanding they move aside for them and their entourage.
  9. A seemingly desperate person with their child attempts to haggle with a food merchant nearby.
  10. A beggar asks the party for some coin or food.
  11. A dog darts past the party with a well-dressed, noble-appearing individual running and calling after them. If the party helps the noble retrieve their dog unharmed, they are rewarded 2d12 gold pieces.
  12. A group of people gather outside a tavern, challenging each other to arm wrestling matches while spectators place bets on who they think will win each match-up.
  13. A veteran adventurer recognizes the player characters as kindred spirits. They offer the party a drink and some company for the evening. This adventurer has some information concerning the party’s current goal but not that much.
  14. A traveling merchant with exotic and rare items for sale sets up shop in the market. The have a number of spell components, foci, and a few uncommon magic items available for purchase.
  15. A water spirit appears from a fountain on the street the party walks down. This spirit offers anyone who enjoys the waters of the fountain a boon to their health. Any creature who drinks from the fountain gains +5 temporary hit points for 24 hours and gains advantage against poison.
  16. A wagon passing by hits a bump in the road, dropping an uncommon magic item. If the party returns the item, the merchant rewards them for their honesty and either lets them keep it or take 1d4 x 100 (or up to you) gold pieces. If the party keeps the item without attempting to return it, the merchant doesn’t notice until several days later and has little-to-no methods of finding the item.

D&D City Encounters: Tier 2 (5th-10th Levels)

  1. One of the statues in a city square animates and goes on a rampage. Use the Stone Golem stat block.
  2. A pair of Vrocks escape from a mage’s study and begin wreaking havoc throughout the city.
  3. A Dust Devil manifests in the middle of a street and starts damaging property and harming by standers.
  4. A foreign dignitary’s procession begins passing by the player characters moments before a pair of Assassins emerge and begin attacking the procession.
  5. A Succubus / Incubus in disguise approaches the player characters claiming to be an old acquaintance and attempts to charm one of the characters.
  6. The party comes across someone running a shell game on the side of the street. This individual calls them over to try their luck and wager an increasing amount of gold pieces for three tries; the player character wins, the game runner doubles the number of gold wagered. The person running the game plays fairly for two rounds with a character succeeding on a DC 10 Wisdom (Perception) and DC 12 Wisdom (Perception) check for each round. However, the game runner cheats on the third round and slips the ball out from under the cup. Spotting this requires a DC 22 Wisdom (Perception) check.
  7. A parade procession takes place down the main streets of the city. The most perceptive of the player characters notices a few pickpockets making their way through the gathered crowds.
  8. A temple undergoing renovations and construction suffers a massive collapse, trapping multiple workers, temple staff, and by standers beneath piles of rubble.
  9. A pair of horseback-racing nobles rapidly come up from behind of the party, threatening to run them over if they don’t act quickly enough.
  10. A small band of musicians perform on the street side. Some of the city folk stop and toss a few copper pieces in a nearby crate.
  11. A local tavern declares a drinking contest for that night. The winner of the contest takes home the 3/4 of the registration pot with a 5 silver piece entry fee per participant.
  12. A sweet smell drifts from a nearby bakery, catching the noses of the player characters. This bakery presents many brightly-colored pastries including enchanted cupcakes. Each cupcake costs 25 gold pieces and restores 1d4 + 1 hit points when consumed.
  13. The most observant of the player characters notices a book store advertising affordable spell scrolls. This store has a small selection (1d8 + 2) of spell scrolls including spells ranging from 1st- to 3rd-level spells at slightly cheaper than normal prices.
  14. The most observant of the party hears the shouts of terror resonate from a nearby alley. They find a young, noble-looking child being accosted by a small group of shady-looking figures (use the Bandit stat block). Should they run off the ne’er-do-wells and help the child, they’re quickly approached by a nobleperson on the street, thanking the player characters for finding their child. This noble offers a favor in return for the party’s help.
  15. A retired adventurer spies the party and offers them a pack full of single-use magic items ranging from potions to spell scrolls all of which are of rare or lower quality.
  16. A beggar asks the party for either a few copper pieces or bit of food. If the party treats them kindly, the beggar thanks them and disappears down an alleyway. One of the player characters then feels their pack grow slightly heavier as a rare magic item appears within it.

D&D City Encounters: Tier 3 (11th-16th Levels)

  1. An Archmage and their followers attack the city folk in an attempt at grabbing power for themselves.
  2. A mysterious, robed individual approaches the party offering them a deal; one player character receives a single use of the wish spell on behalf of their employer in exchange for a favor. This individual is a Rakshasa in disguise and works for as powerful Pit Fiend vying for a position as an Archdevil.
  3. Some time after sundown, the most observant player character hears a scream tear through the quiet night. Should the party investigate, they come across a Vampire with 1-3 Vampire Spawn (depending on the party’s level) assaulting a man and woman in a nearby alley.
  4. An experimental, automaton guardian (use the Iron Golem stat block) designed by a state-affiliated mage malfunctions and rampages through the town, destroying property and injury many of the populace.
  5. A massive earthquake tears through the region, demolishing several buildings in the city. Fires break out and many become trapped beneath the rubble.
  6. An invisible pickpocket attempts to steal from one of the player characters. The player character notices if their passive Perception is over 20.
  7. A local scholar stops and asks the player characters if they’re willing to participate in magical potion trials. The scholar is willing to pay 50 gold pieces per participant, per potion tested. Should a player character participates, roll on the Sorcerer’s Wild Magic table to determine the effect of each potion tried.
  8. The party passes a loud, over-the-top argument between two seemingly romantically involved individuals.
  9. An acting troupe performs a scene on the street as a way of advertising their show that night. They hand out flyers and ask bystanders to attend
  10. An artist calls from their market stall, offering to paint the party. The painting costs 100 gold pieces but has a slight animation to it through the use of enchanted paints.
  11. The party comes across a rather boisterous adventurer regaling a small crowd with their exploits. This adventurer recognizes the party as fellow adventurers and begins recounting the first time they saw the player characters to the crowd as their inspiration for setting out on their own.
  12. A local book store advertises a partnership with a magic academy. As part of this partnership, they now sell a wide variety of spell scrolls priced with students in mind.
  13. One of the noble families of the city have taken notice of the player characters’ adventures and exploits. They’ve stayed up-to-date on news regarding the party and wish to extend their assistance when / if the player characters should like. This is explained by a courier under the employ of the noble family.
  14. The party notices a flyer advertising a galley or airship for sale at 75% of the normal cost. It’s to be retired and dismantled unless someone purchases it.
  15. The local mages’ college advertises a festival to introduce the staff and new year students. This festival is free for anyone to attend offering free food and beverage for guests. If a character spends at least one hour attending the festival, they gain the benefits of the heroes’ feast spell as if it were cast as a 6th-level spell.
  16. A very rare magic item catches the eye of the most observant player character simply sitting on a crate down an alleyway. No one else around seems to notice it until the character picks it up.

D&D City Encounters: Tier 4 (17th-20th Levels)

  1. An Ancient Red Dragon and their minions descend on the city, intent on destroying it.
  2. A dozen 80-foot diameter meteors appear above the city and descend rapidly, destroying large swaths of the city. The player characters have enough time to react to 1d4 of the closest meteors before they impact.
  3. Dozens of devil-worshipping Cultists open a portal, allowing a Pit Fiend and several lesser devils to pass through.
  4. Hundreds of different types of oozes start emerging from drains, wells, and fountains across the city and keep appearing, amassing a huge number and causing panic amongst the populace.
  5. The party notices a thick plume of smoke rise into the sky a few streets over. A massive fire has broken out and is spreading rapidly from building to building.
  6. One of the local taverns starts shifting from its place on its own, speeds up rapidly, and starts careening down the city streets. The party hears the screams and destruction as the building rounds a corner and rushes down the same street as the player characters.
  7. A group of young punks bump into one of the player characters and act generally rude towards the character. These punks use the Commoner stat block and don’t seem combat capable, just young and arrogant.
  8. A local shopkeeper calls to the party asking if they’re interested in purchasing their latest stock of necklaces fresh in from the greatest dwarven jewelers.
  9. A baker shouts and rants while gripping onto the arm of a young child who holds an armful of bread loaves. The baker mentions turning the child into the guard for stealing the bread.
  10. A very confused looking Archmage stumbles about the street asking what year it is and what city they’re in. They don’t seem to recognize anything but insist they’ll be fine on their own.
  11. The city holds a fireworks show that evening. Exotic vendors from around the region sell unusual goods including enchanted food and valuable trinkets.
  12. An escaped Blink Dog from a local mage evades capture with a small, rare magic item in its mouth. The mage declares anyone may keep the item if they catch the Blink Dog without harming it.
  13. A emissary from the fey realm brings a magical garden with them to the city. This garden seamlessly intertwines with a section of the city streets with exotic plants magically adapting to the shape of the road and buildings. All of this culminates in a sort of street fair with vendors of both the city and fey realm selling their best wares including some enchanted, single-use magic items. Anyone who spends at least an hour at this garden festival also gains advantage on Wisdom and Charisma saving throws for the next 24 hours as the magic of the fey binds itself to the attendees.
  14. The party comes across an estate sale of a former adventurer. Many magic items of rare and lower quality , even a few very rare enchanted items, and many art objects of varying price are up for auction. Additionally, the estate itself becomes available for purchase also through an auction.
  15. One of the professors from the mages’ college wishes to try out using a new spell. They wanted to monitor a duplicate of a chosen creature to see how closely it behaves to the original. One of the player characters has a duplicate made of them through the use of the simulacrum spell so long as they agree to report their observations back to the professor.
  16. A friendly, seemingly homeless individual offers to help the party with their journey. This person reaches into their tattered cloak, producing a very rare magic item; they then promptly dash into the nearest alley and vanish from detection.

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