If you’ve ever sat down to make a city the traditional way, you might say a dungeon or a village, and you’ll immediately realize why cities are few and far between in ttRPG products nowadays. They’re huge endeavors, massive timesinks, and they offer almost too many options to the players that prevent you from knowing where they will go next.
In short, they’re a metric shit-ton of work for what seems, at least at the onset, like a minimal amount of viable product.
Or is it?
A city is, after all, just a large town. And I believe there’s a simple way to go from small town to big city that doesn’t require you to make a hundred taverns, eleven guilds, or a region’s worth of politicking:
You make the city what the town isn’t: the potential to be dangerous.
Encounters in the Big City
According to the prevailing advice in the ttRPG sphere, towns are safe places where players can plan, rest, trade, and pass time. The adventures, dungeoneering, and wilderness? Those are all beyond the town’s border.
The city, though? All that stuff is right here — and it’s not waiting for you to leave a certain area to get in your face.
Take, for example, a bog-standard quest: the blacksmith’s neice/nephew has been taken by goblins to the nearby forgotten mound. In a town, it goes like this:
Party finds blacksmith
Party gains quest
Party prepares and leaves for mound
Potential for Random Encounter along the way
Party investigates, infiltrates, and finds hostages
Party talks or fights their way out with said hostages
Party returns to town and gets paid
Potential for Random Encounter along the way
Pretty standard stuff and you’ll notice that on the way to and from the mound are when random encounters are potentially found.
But let’s see what that looks like in a city:
Party finds blacksmith
Potential for Random Encounter along the way
Party gains quest
Potential for Random Encounter along the way
Party prepares…
Potential for Random Encounter along the way
… and leaves for “mound” (more likely hideout or sewer or something)
Potential for Random Encounter along the way
Party investigates, infiltrates, and finds hostages
Potential for Random Encounter along the way
Party talks or fights their way out with said hostages
Potential for Random Encounter along the way
Party returns to town and gets paid
Potential for Random Encounter along the way
Risk (or Reward) Around Every Corner
When the party leaves their place of safety to go find the blacksmith in a city, they’re likely not crossing the road - they’re traveling to a different neighborhood entirely. This allows for all sorts of shenanigans to happen in the meantime:
They run into a rival
They are tailed by a group of thugs
They’re followed by a thief
They’re accosted by merchants plying their daily deals
They witness a crime being committed
They see a cart careening down the road out of control
They see a building on fire with people still inside
They see a character from one of their backstories
They run into a VIP that they gain or lose favor with
and on and on and on…
To be clear, you can do these things in a town too - but too many of them doesn’t suspend disbelief.
In a one-road town, it’s hard to have the party tailed by a thief, a building catch on fire, a runaway cart rush past, and get ambushed by a group of thugs without making the town seem like the most dangerous place in the world.
In a city, though? This feels like par for the course.
But What About All the Buildings? And Factions? And—
Don’t worry about all that stuff. Seriously. That will all come up naturally in play as the party finds their way around the city. Come up with the basic necessities like you did in a starter town and just go from there session by session.
A good way to start is to have the following as your base:
A place to buy, sell, and maintain weapons and armor
A place to buy, sell, and maintain adventuring gear
A place for each of the four archetypes in a fantasy game (fighter, magic-user, cleric, thief) that they’d be interested in
Fighter’s Guild or Arena for Fighter
Mage’s Guild or Library for Magic-User
Temple or Place of Worship for Cleric
Thieves Guild or Seedy Tavern for Thief
A place to rest and relax, like an Inn or Tavern
A place to gather information, like a Job Board or Market
Everything else can spin off from the random encounters between where your players want to go.
Encounters in the City: A Resource
Didn’t think I’d leave you hanging without a download, did ya!?
Check out d100 Encounters in the City for all the rollable random encounters stuff I mentioned above. Making the city is easy, and with this download, filling in the cracks can be even easier.
Thanks for reading!

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Space Pirate
100% in agreement with skip the faction planning. That can come naturally and otherwise would lead to more railroading or lore dumps that’ll tire most out imo
Cool, I’ll check out the resource later