One of the most fascinating settings in any Dungeons & Dragons campaign is a city. From a medieval metropolis to an industrial powerhouse, it can be exciting to have a campaign arrive at a large spanning setting where practically anything can happen. It's to the point where you could even have some campaigns have a city be the main setting, with monsters, thieves and other threats crop up in the underbelly of a city.
However, because cities are so large, there tends to be a case where you're spoiled for choice over what to throw at your party. You could theoretically do anything from an attack from Mindflayers to a gang of thieves trying to rob them. But if you're looking to add a little extra spice to your encounters, then here are a few that you can throw at your adventuring party when they find themselves in city streets.
6 Magic Merchant Machines
It's always interesting to think about how technology would progress in a world of magic. Much like fiction, Dungeon Masters are allowed the freedom to come up with their own worlds or even versions of settings released by Wizards of the Coast and so imagine just what this technological progression would look like. One idea to have in a city would be vending machines, or at least something similar that could get you the best potions or other items gold can buy.
Imagine a sort of stone construct, whether like an actual vending machine or simply some sort of slab with shelter like a small wooden rooftop. Upon this slab or platform are the runes that are a small Teleportation Circle, except it seems to be rearranged slightly, the runes not properly put together for some reason. All one has to do is look at some writing, perhaps a protected piece of parchment, on potions or other basic items they could order and how much gold it costs. They place the amount of gold and some writing on parchment for their order and push a button. The stone rearranges so that the teleportation circle moves and rearranges to form the proper circle and runes. Gold and parchment disappear, and the item appears shortly after.
5 Kids These Days
Dungeons & Dragons can be so wholesome, and what could be more wholesome than some kids, especially kids that look up to the party? However, these aren't the kind of children who need to be saved or are solely there to admire the party — they have questions. As the party are walking down a street, a small group of kids, around three to five, approach them excitedly and ask if they're adventurers.
Upon confirmation, the children will excitedly ask questions about what adventuring is like, what their roles are and any advice for them. These kids clearly want to be adventurers. However, whether the party will tell them the ugly truth about such a risky career or take a bit more of a gentler approach is something to be seen.
4 The Last Delivery
Some of the best kinds of encounters are the ones that can set things up in the future and that's exactly what this is when players come across a courier being attacked in an alleyway. If they are assisted, the messenger is too badly hurt to carry on and without healing will soon perish. Even if they are healed, they will come up with the excuse that more people will be after them and that they've been compromised. Either way, whether it's their dying request or a quick plea, they will beg the party to deliver a letter of great importance to somebody. If you want, you could even have the encounter turn into an escort side-quest to protect the courier on their delivery.
If the party try to look at the letter, it will magically burst into flames, as if knowing that it isn't being seen by the right eyes. Whether they fail to deliver the letter or succeed isn't important immediately, but this is a nice encounter to set up a future questline where the party's decisions in this encounter can have all sorts of effects on a quest surrounding this mysterious message and its fate sessions later. Don't forget that, in a city, you're likely to have all sorts of groups and guilds involved, so having a thieves' guild, for example, that wanted the delivery or that have more information can be helpful for future plans.
3 We Have To Band Together
The party comes across a frantic figure who is strumming a lute nervously and striding up and down outside a tavern. When they spot the party, they waste no time being thankful to see a group of talented-looking people to grab and ask for help. It's not a monster that needs slaying or something that needs collection; it's a show that must keep going. The bard explains that a band he's hired has gone out sick with a recent illness going around, and he doesn't have the money to buy them any potions to stop the disease or hire a cleric.
That's where the party comes in, as the Bard begs for them to head into the tavern and perform with them. They can perform a well-known song or freestyle, whatever it takes to get the show going. This is a great encounter especially if you have a Bard in the party. Let's just hope the party manage to pass their performance checks.
2 The Street Act
In a city, there's always something going on. Sometimes it's the illicit dealings of the criminal underbelly or just the machinations of the local politicians, but often it's just people living their lives. A popular thing to see in most city streets would be performers, especially of the magical kind where spells like Prestidigitation or Minor Illusion can go a long way to impressing a crowd of commoners.
But when a street act goes too far and a magician accidentally summons a monster, the party has to step in to stop a demon, elemental or another creature of your choosing from causing chaos in the streets. This is an easy-to-run encounter, with it also being quite easy to have a monster planted in the city uniquely, while being able to change what type of monster this is, so it's balanced well for your party.
1 Hostage Situation
This is for when the party are in a crowded place like a market. Those perceptive enough witness the end of a chase as someone rushes after another and catches them. They then fire something in the air, perhaps the bullet of a firearm or a flaming spell out the end of a wand, as the party realises this is a hostage situation. Now, this is the kind of encounter where you would have to put in a bit more work. Why is this person being taken hostage? What was the chase about? What's the end goal here?
Of course, to make things more intense, the town's guard could soon be involved, perhaps even with a couple of them being part of the chase. Will the party enter combat and try to save the poor hostage? Or will the party's face lead a negotiation to a peaceful conclusion to this encounter?