How to Create and Run Urban Encounters in D&D 5e

Urban encounters in D&D 5E are defined by the presence of law enforcement, civilians, and the unique enemies that populate a fantasy city. Players are never entirely alone while they are within a city’s walls. The human element within an urban encounter infuses tension and emotion throughout. If you ever wanted to run an urban encounter, but don’t know where to start, this article is for you!

What Defines an Urban Encounter?

Law and Order or Lack thereof

Rules… Without them, we live with the animals!” -Winston, John Wick 2

How a government handles disturbances is the key factor in any urban encounter. Decide for yourself the following three things:

  • For this town, what alignment is the average guard or law enforcement? 
  • How well are they trained and equipped? 
  • What is their standard response to a violent encounter? 

Understanding Guard Alignment

Alignment is brought up here to help you determine how likely law enforcement is to follow the law and to what ends they do it. It will also explain their relationship to the players quickly. If the Guards are Neutral Evil and are called upon to arrest a powerful group of adventurers for starting a drunken brawl, they’re more likely to let them go in exchange for a personal favor rather than arrest them and charge them like normal people. 

How well the Guards follow the law also dictates the player’s methods while working in town. If the Guards are Lawful Neutral and arrest anyone when they do something wrong regardless of stature, that encourages players to think creatively when trying to solve a problem like breaking into the warehouse they believe their friend is being held. 

Their general strength and ability to help or hinder players matters a lot. If the players are chasing a serial killer and the local law enforcement refuses to help, that tells us: they don’t care, they are incompetent, or are otherwise occupied. If those same players that needed help with the serial killer get in a drunken bar fight and guards arrive to arrest everyone, that tells us they value quiet more than they value justice. They are probably Lawful Evil. 

Shortcomings of City Guards

If the guards are too effective, then there isn’t really a need for heroes. Urban encounters often need a component to them that neutralizes or works around law enforcement as a whole. For example,a Vampire who is also a City Councilor will likely have a lot of influence and be able to convince officers that they are either above the law or threaten to fire them if they intervene.

Criminals that have worked in a city for a long time will be excellent at evading law enforcement. They will know when to strike and how long it will take law enforcement to get there. Modern-day police with call centers and vehicles can sometimes take nearly half an hour to respond to a 911 call. Imagine what that would be like before modern conveniences. 

Players having encounters in Urban settings should almost always be doing something that law enforcement can’t or isn’t equipped to handle. The range of that can be everything from stopping a hostage situation in progress, solving magical crimes that require special skills to investigate, to dealing with a Goblin problem that’s too dangerous for the commissioner’s conscience to send men with families to fight. 

Civilian Concerns

Civilians in the D&D sense are generally a passive force in an encounter but they are still witnesses and environmental hazards. 

Being a witness can be more than just seeing and saying something to law enforcement. Word gets around the town of the heroes of villains affecting it’s day to day life. Even if this town doesn’t have a functioning press corps or a town crier, gossip always finds its way. This can help or hurt your players if their reputation is terrible or honorable. This can influence the way shopkeeps and innkeepers interact with the players. 

Don’t forget, road rage is as old as roads themselves, even Ancient Romans had problems with traffic. A city that is alive will have activities that can help shape encounters. Maybe there’s a parade going on at the same time that the players are being chased by assassins. The players could blend in with the crowd and stealthily turn the tide on their pursuers. Conversely, if they are being pursued within a crowd, your local Wizard or Sorcerer will have to rule out casting Fireball unless they want to be ripped apart by an angry mob or be chased by law enforcement for the rest of their lives. 

Camouflaged Monsters

At the back of the DMG from pages 302-305, Wizards of the Coast suggest monsters for every environment including Urban. There are humanoid stat blocks like Spellcasters or Bandits, but what we’re going to focus on is the kinds of inhuman creatures that have kept up with the times. 

Broadly speaking, Urban environments are the happy hunting grounds of creatures that can shapeshift or look human. A short non-comprehensive list of these beasties includes:

  •  Cambions
  • Doppelgangers
  • Oni
  • almost any variety of Vampire
  • and Succubi. 

Their methods should reflect their relationship with the city as a whole. Given the bulk of them are predators, they’re likely to prey on the poor and the forgotten people within a city. That means the homeless, runaways, elderly, sick, and anyone else who can’t fight back is fair game. 

Since their presence in the city is contingent upon their appearing human, they will fight tooth and nail to protect their reputation whatever that is. Exposing them as monsters to the general population should be difficult and should increase in difficulty the more influential they are. Bards were notorious in Celtic history for being able to shred the reputation of leaders and should be feared by these kinds of monsters. 

The other variety of monsters to look at are those that are more comparable to animals, that learned how to blend in with the environment rather than the people. These kinds of monsters include: 

  • Mimics 
  • Gargoyles 
  • and Water Weirds 

Civilians could walk past these specifically every day and not be any wiser. They are more on the animal level of intelligence so they likely operate in things like sewers, cemeteries, or abandoned warehouses with as few witnesses as possible while still having some foot traffic. They won’t have social considerations, but they’re likely to know their environments pretty well and will be able to navigate better than someone who’s new in town. 

There are only three other categories of creatures you might run into, but they aren’t as complicated. 

  • Wild undead (Specters, Ghosts, Poltergeists. etc.). are possible enemies at sights of murders of graveyards. 
  • Monstrous varieties of normal creatures (giant centipede, swarms of rats, giant wasps) will crop up in derelict areas without adequate protection. 
  • Yuan-Ti, Kobolds, and Half-Ogres make up a small category of “humanoid but not quite” creatures that can disguise themselves with just cloaks and masks that you might encounter in small organized units, but likely aren’t the apex predator of an area. They are more likely to be trying to survive like everyone else. 

What are some types of Urban Encounters?

Faction on Faction Conflict

There are many factions, both known and underground operations, that fight for territory in a city. Guards and the local Gang can be in open warfare. Two rival families, like the Hatfields and McCoys, can be competing in matters of honor. The Thieve’s Guild and the Tax Authority might be in conflict over how the Thieves are reporting low income but can afford land worth 30,000 Platinum pieces. 

Important to remember with factions, they have reputations and connections. They can call upon friends to do favors like moving goods or making crime scenes disappear. Simply having more active members can do a lot for power imbalances, be they magical or martial. However, if the group starts to get a bad name or attract too much attention, they may need to reorganize or go underground if they want to keep a good grip on members.

How players resolve conflict or even what side they choose is always fascinating. 


Between private eye tales and horror mystery stories, there are a million things to draw inspiration from. Investigating an assassination by questioning witnesses, tracking the kind poison used, and figuring who had access to what and when always changes the priorities of players

The roleplay of tracking a criminal coming to a head with combat can be anywhere from a flash in the pan to a slow burn adventure. 

External Threats

External threats in a D&D urban sense would be something that threatens everyone in the town that originates from a source outside of the town. This can be anything from a flood to a plague to an invading band of Orcs that have breached the walls. How the players handle the situation is unique in an urban setting because of the responsibility and weight of the struggle. The urgency is turned up as every second they waste someone might be dying. 

Pest Problem 

The term “pest” here refers to any creature that requires a different set of skills than the average guard. In the real world, police are not called in to do the jobs of Big Game Hunters or Exterminators. Each division has special training that sets them apart. Even within urban environments, there are monster hunters. 

For example, your players might be contacted to deal with what the Guards think is a wild animal that is attacking construction workers at night near a dig site, but it turns out to be a Gargoyle that is mounted on the nearby building that was attracted by the noise. Reversals and surprises can be super easy within an Urban setting. 

Chase Sequences 

(For a refresher on chase rules, please check out the DMG. pg. 252-255.)

If you’ve ever played Assassin’s Creed, you know how fun this is. Being on the run, dashing through buildings, jumping behind cover, all with your pursuers on your heels the entire time. Dashing through buildings is so much fun that the DMG literally expects you to and has SEVEN pre-built tables to help (DMG 113).

For example, your players are running from a Debt Collector who has mistaken them for someone else and isn’t taking no for an answer. They run for three actions straight and we need a complication. You roll a d20 on the Urban Chase Complication table (DMG 254) and the complication is a beggar laying in the road. You could try to push past, jump over, or scare him, OR you could pay him a comfortable sum of 5 Gold to get out of the way and trip the Debt Collector as he goes by. 

We know it can be difficult to plan ahead during a chase sequence, so we encourage you to consider what part of town your players are in and select the hazards accordingly. This will help you tailor the experience to the town and make it feel dynamic and alive. 

For example, the town may have a zoo they are known for. If your players dash through, you can require an animal handling check as they pass by the Owlbear cage, provoking an attack of opportunity on a failure. This may even slow their pursuers if they’re knocked flat on their back. 

…and Carousing

Once again, the DMG expected this (pg. 128). However, let’s talk about how to use these tools rather than just pointing towards them. 

During a night of carousing, the DMG recommends rolling a D100 + player level to determine the outcome. Let’s say the player rolled a 25, this means they now have made an enemy. The DM decides the offended party and the player decides what they did. While it is up to the player to decide how they offended their new enemy, if they are having trouble thinking of something or say “surprise me,” consider the following story: 

“During all the merrymaking as the party relaxes and spends some of its hard-earned gold, your Wizard player finds themselves chatting up a local anti-war protest group. With their guard down and some drinks in their system, they may find themselves persuaded into joining in on a demonstration in front of the local Guard Garrison. The protest brings their drinks with them and throws them at the walls of the Garrison. 

Your Wizard then intends to create a light burn mark as graffiti, and casts Firebolt. The alcohol catches alight and even reaches one of the windows with a bedroll that also catches flame. The visiting dignitary from a few towns over who was staying in the Garrison for safety awakes to his hair ablaze. He looks out the window and meets eyes with his new enemy.” 

Always remember to personalize the flavor of your encounters and have fun with whatever the dice roll and work it to meet your players. 

I only have 15 minutes to prepare for an urban encounter for my players. What can I do to make it work? 

Ah yes, DM crunch time. I know it well. Here’s your ultimate quick build! We’ll list the steps as we go and build an example alongside. 

Get your town’s name: Click the hyperlinked text and go to Fantasy Name Generator’s auto-generated names and click “Get City Names” until you find something you like.

Example: Xico 

Roll a d20 + d8 on the Random Urban encounter table (DMG. 114)

Example: 11, there is a fire. Your players will have the opportunity to put it out before it consumes a building or hurts anyone. 

Roll a d20 and determine the nearest building that will be on fire (DMG. 113):

    Example: 18, there’s a Shop nearby

Since we rolled a shop, we now roll a d20 to find out what kind of shop (DMG. 114)

Example: 1, it’s a Pawnshop. Maybe the shop keeper will feel like giving some of the goods after they save the building. 

For additional details and story developments, consider the following:

Roll a d20 on the Current Calamity table: 

Example: 9, there are Marauding monsters. It’s possible the fire could be their doing. For a list of possible monsters, consider the recommended monsters for Urban encounters on DMG 305. 

Roll a d20 on the Race Relations Table (DMG. 112): 

Example: 14, there’s racial tension rivalry. The fire could be arson by someone trying to drive a Half-Orc shopkeep out of town. 

Roll a d20 on the Ruler’s Status (DMG. 112): 

Example: 7, Xico is ruled by a feared tyrant. Authoritarians come in all styles, so this could go any direction. For this example, we’ll say he’s a laissez-faire tyrant that considers building fires a problem to be solved by the citizenry. The Half-Orc who owns the shop could report the fire, but it wouldn’t go anywhere. He may ask the players for help dealing with the attack on his shop. 

The details of this story were all generated just using the tables in the DMG, one website, and some speculation and it has the makings of a good session. There are even more tables and resources in Xanathar’s Guide to Everything. Don’t have it yet? Click the link to buy it and save $10 off retail price! (I love Noble Knight Games!) 

Let’s say you’re struggling to know where to go next now that you’ve survived the first random encounter you had to throw together on the fly. Ask your players what they think is going to happen next. What’s incredible about the human mind is its ability to recognize patterns. When you present events or information in order, your players can take over and start seeing the storyline sometimes before you do. They can make order out of chaotic rolls and that’s honestly beautiful. 

DM Tips to remember for Urban Encounters

Cities have personalities because of their inhabitants, what binds them together? 

If everyone knows that the Baker on Kingston Road has ants baked into the bread, it’s going to come up. There will be phrases and nuances that are familiar to residents or frequent commuters. 

Your players might not have any preexisting knowledge of the town, but their characters might. 

Think about your player’s character backgrounds and what they might have done in the past. Even in the past, peasants had to travel into town to trade for goods. Soldiers had to go to fortresses to train. Scholars had to go to school somewhere. Having knowledge of the area as they arrive at it helps a player feel integrated with the world. 

It’s ok if you don’t have every avenue planned and prepared. 

To quote the DMG: don’t worry about naming every street and identifying the inhabitants of every building; that way lies madness

Weather can still be horrible behind city walls. 

While many wilderness effects are not applicable to an Urban setting, rain falls on the city and country alike. Feel free to use appropriate weather effects (DMG 110). If it’s the middle of a winter night and your players are running all over town in sub-zero weather, they might be risking frostbite. 

In conclusion…

Urban encounters are some of the most diverse and interesting storytelling environments out there. You can tell almost any story humans can create within it. There are loads of charts and tables to take the headache out of running them, so don’t be afraid to try out city life in your campaign!

Until next time, my friends,

May your game have advantage!

-Halfling Hannah

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