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| The Free City of Greyhawk Artist credit: Valerie Valusek |
I've spent a lot of time in the last year thinking about adventuring in cities. Part of it's because I really miss going outside and having an active life in an urban area. Part of it's because my D&D group spent the better part of 2020 in a campaign arc involving our party trapped in a hostile city, Escape From New York-style. And even when we broke from that for a few one-offs here and there, many of those involved adventure in the city. Or at least, like, in a town or neighborhood. And I've noticed what's worked and what hasn't and I've done so much darn reading and I want to get this right once and for all. I've run games in this setting with different approaches and sometimes it's good and sometimes it's not. And I've tried to give feedback to my own DMs about how they might want to improve those sessions, and sometimes they take that advice and sometimes they don't. But the worst thing of all is that each of the really solid sessions my group has spent playing in an urban setting have largely relied on the strength of completely unrelated elements, like a fun combat encounter, social encounter, puzzle, or whatever. They always just skirted around the problems of answering those vital questions about city adventures, so even if the session was successful it was at least partially just luck.
Here's a brief table of contents for this post:
- Bibliography for research I did, and further reading you may enjoy
- An analysis of how most people seem to run urban settings
- An explanation of my line of thinking that led to my version
- My Brave settlement guidelines and examples, with a bit of elaboration on certain parts
- Why I care so much about this
If you just want the goodies, you can skip down to the 4th part.






