A Thorough Look at Urban Gameplay in D&D

The Free City of Greyhawk
Artist credit: Valerie Valusek

See, the title is like a Noah Caldwell-Gervais video. Get it? Because I'm about to spend a lot of words being pretentious but hopefully insightful.

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:

1. Bibliography for research I did, and further reading you may enjoy
2. An analysis of how most people seem to run urban settings
3. An explanation of my line of thinking that led to my version
4. My Brave settlement guidelines and examples, with a bit of elaboration on certain parts
5. Why I care so much about this

If you just want the goodies, you can skip down to the 4th part.

1. Bibliography

So first, I'm going to list below some of the preliminary reading and research I did. This is partly because it may interest you and partly because I don't want people recommending me stuff I've already read. Or if they are recommending me something new, they might read this list and realize "oh, wait, the thing I'm recommending won't actually add much to what this guy already knows." And you might also be interested in these things. A lot of ideas in here I ended up not agreeing with, but you might.

1. Vornheim (obviously), the beloved LotFP supplement by the infamous Zak S
2. Electric Bastionland, the beloved "Vornheim replacement" by the equally-beloved Chris McDowall
3. Magical Industrial Revolution, by Skerples
4. Demon City, the modern urban horror game by Zak S
• I backed the Kickstarter literally years ago and got the unformatted draft PDF. There was some pretty good stuff but overall it's not great and it ended up telling me basically nothing that would be useful to this project.
5. Yoon Suin, by Noisms
6. Maze Rats, by Ben Milton
7. Augmented Reality, the cyberpunk city kit by Paul D Gallagher
8. Torchbearer, the dungeoncrawl spinoff of Burning Wheel, by Thor Olavsrud and Luke Crane
9. Mausritter, by Isaac Williams
10. Blades in the Dark, by John Harper
11. Waterdeep: Dragon Heist, by... uh... Wizards of the Coast, I guess. Whatever, it really sucked anyway.
12. Medieval Demographics Made Easy, by S. John Ross
13. The Alexandrian's long, long series on Urbancrawls (that's very good!)
• Contained within this is an account of many, many other gaming resources that you could also consider to be part of what informed my thinking here, even if I only read about them second-hand
14. The follow-up by Gnome Stew
15. Layers of London, a website dedicated to preserving the history of London, which has a really good "medieval London map" layer you can apply
16. The iconic HEX campaign, by Bearded Devil
17. Noisms's blog post on the subject
18. Detect Magic's city procedure
19. "Street Guide Without Streets" by Roles, Rules, & Rolls
20. A lot of Wikipedia, but I specifically kept coming back to this article
21. A series of articles on crawl structures that talks a fair amount about cities
22. The Tome of Adventure Design by Matt Finch of Frog God Games

2. Where we've gotten so far

Okay, so for those who've attempted to take a firm stance on "how to properly do cities in D&D," I've found two really popular lines of thought:

The first is to not play in cities. These folks argue that cities are basically a red herring, and that you should keep play focused on what the game is really about: dungeons. The role of any settlement in your game should basically just be "the place where players rest in between sessions, off-screen." They might be a bit more generous and say, "sure, they also shop here and get their quests from employers here" and maybe they'll even be nice enough to have some kind of carousing rules. But they insist that adventure is out there. This is largely the approach of Keep on the Borderlands (although some groups end up playing around with the inhabitants of the Keep quite a bit), Torchbearer (which divides every session into distinct, inflexible phases: town, journey, camp, dungeon, camp, return, town. You literally cannot adventure in town, since the rules don't support it), and the original West Marches campaign, in which the DM explicitly says:

The adventure is in the wilderness, not the town — As per the discussion of NPCs above, be careful not to change the focus to urban adventure instead of exploration. You can have as many NPCs as you want in town, but remember it’s not about them. Once players start talking to town NPCs, they will have a perverse desire to stay in town and look for adventure there. “Town game” was a dirty word in West Marches. Town is not a source of info. You find things by exploring, not sitting in town — someone who explores should know more about what is out there than someone in town.

I can appreciate this a lot. It's a noble creative direction to commit to. They have a vision they're seeking to create, and a sudden murder-mystery noir investigation session would be completely at odds with that. Each of these examples uses a basic cycle of "prepare in town, go out and adventure, then recover in town again" like in Dragon's Crown or something. And that's fine.

But obviously, enough people are interested in town adventures that this cannot be the only solution for everyone's tables. If my players get hired by a scheming noble to go retrieve an artifact from the dungeon, and then when they deliver it he doesn't pay them, then they're going to want to take him down. That probably means having a session or two take place entirely within the city and performing a heist. In my experience, no matter how much focus I place on the "dungeoncrawl cycle," there will inevitably come a situation where players have something they really want to do that takes place in the city, okay? So that rules out the first line of thought for my purposes.

That brings us to the other line of thinking, which can be summarized as "noir fans really committing to the vision of an all-city campaign and just seriously going all-out with making the urban setting an adventure-able space." Each of the following examples support adventuring in metropolises, and are very impressive: Guildmaster's Guide to Ravnica, Vornheim, Magical Industrial Revolution, Electric Bastionland, HEX, Demon City, and Blades in the Dark. They've all been greatly praised for their innovations in answering the age-old questions of "how to run cities in D&D," with some (mostly Vornheim) even being considered the definitive guide on the subject. But there are some problems that also limit any of these from being the be-all, end-all solutions to our issue.

The first problem is, if I don't plan on the whole campaign taking place in a city, then some of the more interesting features of these games would probably be way too much to include. Magical Industrial Revolution has a feature called "Innovations" that is fucking brilliant and awesome and if you read the book you'll think, "damn, this is such a cool campaign hook I'd love to use"... but it would be wasted on a city that the players spend, like 2 or 3 sessions in. Both Blades in the Dark and Ravnica are built entirely on the assumption that your campaign will center around the PCs being members of a specific faction and being really committed to competing with other rival factions for control over that city. Pretty fuckin' cool, yes. But also, again, kind of a specific premise. Electric Bastionland actually does have some areas outside of the city for adventure to take place, but the city is so central to the whole thing that, well... I'll let Chris explain:

Bastion is an adventure site. It is not a hub. Not a main menu. Not an online shop. People die in Bastion! They get tricked and take wrong turns. They fall victim to industrial accidents. When characters haul the treasure out of the expedition site, and slog their way back through Deep Country or the Underground, they don't get to switch off just because they're in the city. Run it like a dungeon. Draw a map, fill it with odd stuff, punish mistakes. When they go off-grid, roll on tables and make stuff up. People are unhelpful. Places are difficult to get to. Things run bumpily. Finding medical treatment is an adventure. Going shopping is an adventure. Getting the train to the library is an adventure. No fast travel without complications. No downtime without decisions. No switching off. Everything is the game. The game is always on.

Christ that sounds stressful. What if my players do just want the "West Marches cycle" of safety-adventure-safety for a while? If the whole game is just the city, then Chris's Bastionland philosophy makes sense. If not, then it seems like a bit much.

The second problem has to do with size. I've talked about historic settlement sizes before, so I won't retread that ground too much. The point is that medieval cities are really small. Not just in population, but also physical area. They're so small that it's almost impossible for "travel time" when walking through a city to be meaningful. In most medieval cities, you could walk from one end to the other in less than 10 minutes. Here in the 21st century, the general rule for defining a city is a population of at least 100 thousand people. But in Medieval Europe, there were only 2 cities on the entire continent with populations above 100k: Paris and Constantinople. You know how long it would take you to walk across those? Maybe 30 minutes. And think about how far apart they're located. We're talking an average of 2 metropolises per continent. If your campaign is set in a kingdom the size of Britain or Czechoslovakia or something then it might have a metropolis in it. But if so, then the nearest other one has to be about a continent's distance away.

Neverwinter, Waterdeep, Baldur's Gate, etc. are all "anachronistic". That's not a bad thing. There's a reason why people want to play in Victorian London, Los Angeles, Ankh-Morpork, etc. It's an awesome setting to want to evoke. I love noir too. I am not saying that this is a bad thing.

But I'm just saying that, for my historically-grounded medieval setting... this is simply not a thing. And if it's not a thing, then most of the aforementioned urbancrawl resources aren't all that helpful, since they're built on the assumption that the cities my players are adventuring in are much, much bigger than they really are. The borough mapping in Electric Bastionland focuses on "primary transit routes," e.g. trains, metros, canals, ziplines, etc. But those only exist because of modern city sizes. As mentioned, in any medieval settlement, getting yourself from one end of town to the other was so trivial that no one would have ever needed anything more than a simple road. Another example: some of these settings talk about the press and media. A wonderful gameplay element to include in a noir game, right? But those are also a "modern" thing. And yes, they're partially a "modern" thing because of technological advances, but they're also a product of large community sizes. Pre-industrial communities were small enough that either everyone already knew everyone else in town or, if need be, there were plenty of criers and public edict postings for big news to get around.

Neverwinter: "unrealistic," whatever that means

And while I maintain that their "anachronistic" noir metropolises are awesome and good for them, my bigger issue is how many people seem unaware that these are major fantasy contrivances and not at all "realistic" to the theoretical technology situations being replicated in most people's pseudo-medieval games. They simply assume that Medieval London was just as huge and labyrinthine and zany as Victorian London, merely with shittier technology. Check out this bit of worldbuilding from Ben Milton: a city he shared from his campaign... that's enormous. It's at the scale of a modern city, and struck me as though it must have been the center of most activity in the game. But maybe it wasn't! Maybe he just thought that it would serve as a "standard city" for his world, for those parts in between dungeoncrawls when the party is resting up and shopping. Here's a really awesome city generator that u/mathayles created on Reddit that I took some notes from. The main criticism against their method ended up being that the population multiplier of 1000 was ludicrous, which they admitted to not really knowing. A trivial adjustment to make, but a telling oversight nonetheless.

And this bothers me because I can't seem to find anyone interested in supporting urban-play that is both 1) accurate to historical medieval settlement sizes, and 2) sufficient for any range of player engagement, whether they are only interested in cities as "the place we stay in between sessions" or they're interested in cities as "a complicated landscape of relationships, plots, motives, goals, and intrigue that we're gunna get really invested in." Or, y'know, anything in between.

I run a sandbox game. I need tools built for sandboxing. I cannot definitively say how much I need from the cities in my campaign, because my players decide that. I only know that I need to be prepared for both a lot and for very little.

And if you're wondering about the size problem, the other direction is tricky too. You might have thought "well if medieval cities are so small, then just map out the dozen or so buildings in each one and do that for every city in your setting. Can't be that much work!" Nope. Can't do that either! You can't just reduce them to a super tiny little hamlet, because that's not accurate either. You know how in Skyrim or Darkest Dungeon you can just see every single building in town? Yeah, turns out, those are way too small even for a standard medieval village. Waaaay too small. Even small communities like villages or hamlets are still big enough that street-by-street navigation is largely unfeasible, and the list of buildings, or even just shops, would be much too long to list out exhaustively. Even though they might be physically quite small, human settlements are dense as fuck.

Whiterun: surprisingly, equally "unrealistic." Credit here.

Click on that image to look at it up close. Spend some time scanning it. This is a map of the city of Colmar in Alsace (then Germany, now France) in the 14th century. We know it couldn't have had more than 10,000 people, so maybe around 7,000 would be a more accurate estimate. Not a huge amount for the times, but that's still more NPCs than you can make. That's more NPCs than your players can know. And deciding what each and every single one of those buildings is would be unfeasible. Even just the effort it took to draw this picture was more than you should expect of yourself when preparing a city for D&D. And yet, looking at it... you could also, quite clearly, walk across this city in 10 minutes (if nothing stops you along the way). It's the size of a college campus.

This combination of factors defies many of our conventional methods of structuring choice and challenge in tabletop games. The medieval settlement isn't big enough to make movement a reasonable factor. But the settlement has too many people to make an exhaustive map of the place. It's like if you took the amount of content that's in a large sized dungeon and put all of it into one room instead of spread across many. Then you have your players stand in that one medium-sized room surrounded by a ton of potentially interesting elements and try to both explain all of it to them adequately without overexplaining it, and hope they engage with it well. Oh, and without the "room to room and time-consumption by turn" structure tying it all together.

3. I SHALL BE THE ONE TO SOLVE THIS (??)

Okay probably not but I shall be the one to create a solution that satisfies me personally, and if you end up liking too it then maybe I'm onto something.

1. Out of all that research there's some conclusions other thinkers came to which I essentially agree with. The first and most important is this:

You shouldn't draw a town map as a literal map of every street and building.

That's basically useless and way too much work. In nearly all activities that players do when navigating a settlement, it is completely unnecessary and impractical to adjudicate their actions street-by-street, so a map with that much detail just isn't going to get used. Like, you may be familiar with watabou's city map generator, which at this point is probably the leading tool for this purpose in the RPG hobby. It's really cool, don't get me wrong. But... it's kinda useless for what you actually need from a city based on, y'know, the things that players do in cities. As we say, "towns aren't dungeons." Dungeons and wilderness areas are navigated room-by-room or hex-by-hex because they're hostile and tricky and you aren't always sure where you're going and there's a significant risk of fucking up and getting killed and you need to make a map. By definition, that's usually not true of settlements because we create them to be "areas of convenience" (yes, even the ridiculous ones like New York City).

Even if you don't have a map and you've never been there before in your life, you can always just ask locals, follow road signs, and make enough inferences based on your surroundings in order to reliably get anywhere you want to "just by the mere intention." Forcing players to make choices one street at a time is overkill, not to mention monotonous. City streets and intersections, tending to be more uniform than dungeon corridors and rooms, almost never present a meaningful choice to be made. So yeah, most RPGs that feature a lot of urban play will also help guide you in how to run adventures in that environment. And pretty much every time, they'll advise you to accept statements from the players like, "with the info we get from the detective, we head to the murder victim's house to talk to his wife," or, like, "If there's an apothecary in town, I'd like to go to it," and not expect anything further of the player. You don't ask, "okay, how do you get to the murder victim's house?" because that's not really reasonable. What are they supposed to say? Would an answer to that question really make a difference at all? And as mentioned, in the case of medieval settlements, the journey between locations is going to be so brief that I'm not sure how you could even try to make it interesting anyway. I really doubt there'll be that many traps and monsters along the way in the 10-minutes-or-less it takes you to walk to your destination.

And even for the few activities where you do need to "zoom in" that close, there are good systems for generating a local network of streets on the spot. So yeah, don't bother with having a super detailed layout of the settlement. If you already do have a really intricate map you want to use, then that's all well and good. But just understand that you're not likely going to be referencing the really minute details very much if at all.

Instead, cities are better "mapped" as a landscape of people, information, and notable details. General information that characterizes the whole city or the whole district will instead be more helpful in informing most of your content. How wealthy is it? What's the culture like? What is it known for? And you can definitely have specific individual buildings, but just a handful of the "landmarks" or "notable sites" that dot the city. The really interesting places.

2. Of course, even if you're mostly handwaving the transitions between buildings/activities, you still might want to spice up those scenes now and then. If random encounters work for dungeons and hexcrawls, why not put them in settlements? That's the second element I really commonly see people implement.

Well, my feelings on random encounters while "street crawling" are a bit complicated. They're a perfect example of "something that's excellent if the whole campaign is set in adventure-town," but also "something that's way too tedious and unnecessary if the town is just for downtime between the real adventures." I think they make sense circumstantially, like when you're in a dangerous neighborhood or a gated community with armed guards, or if the players declare that they're actively looking for trouble. But I just can't see using them very often. They are one tool in the toolbox but I can't rely on them too much because they shouldn't be happening in, like, 90% of situations where the PCs are adventuring in the city.

3. Some of the most common advice I've seen is to abstract cities into pointcrawls, where the points in question are the big landmarks. A set amount of time passes every time the players move between landmarks, and an encounter is rolled. That seems like a nice and simple procedure, right? Except that, y'know, it's dumb. Defining very few physical routes the PCs can take while traveling in a city makes hardly any sense, since cities are usually freeform enough that there's rarely any reason why you would have to pass through B to go from A to C, assuming there's more than 1 or 2 streets in the city.

Look, pointcrawls do make sense sometimes. Traveling across the United States almost certainly necessitates you rely on the interstate highway, so using a pointcrawl for that context is fair. Better yet, railways are obviously a pointcrawl system by design. Traveling in a dungeon is always limited by rooms and halls, so it's always a pointcrawl. Traveling in the Outer Planes between areas of Hell or Limbo or whatever probably doesn't follow normal geographic rules, so a pointcrawl can't be argued with if that's what the DM is using. But cities usually have lots of streets. That's the point.

To belabor this further, here's a city pointcrawl map I pulled up from a Google search of the word "pointcrawl," which looks to come from a 5th Edition adventure. That doesn't really matter, I'm just gunna use it to illustrate something. The sites themselves aren't bad. In fact, they're great! But then restricting travel in the city to this set of lines connecting them? If I tried using this on my players, the arbitrary constraints of the pointcrawl would immediately frustrate them. Like, if they were at Site 15 and wanted to get to Site 12, but they didn't want to pass by Site 14, then I think they'd be rightfully pissed off that they seemingly have to. Or if they were at Site 22 and wanted to get to Site 9, why the fuck would they have to go through Sites 18 and 20 first when there's clearly other, shorter paths.

The limitation of a pointcrawl is pretty pronounced in a settlement is all I'm saying.

4. The Alexandrian's series on urbancrawls ended up arriving at a conclusion I'll try to summarize as follows: firstly, you will be doing a pointcrawl, but a slightly weird one. Map the city's locations as nodes, connected in a network by relationships instead of physical routes. He still maintains the, "if the players say they want to go to X, they just declare it and they'll arrive there" thing. But their entire knowledge of "what places they can go to" and "why they would go there" comes from the information gathered at each location. Go to a crime scene? It'll point in the direction of the victim's house. Talking to the victim's wife? That conversation points you in the direction of a seedy criminal bar. Talk to the right people there? Find out where the drug supply is kept. And so on.

I will admit that this makes more sense as a way to connect nodes than physical routes do. When every building in town can be reached from any other building in town by the same network of streets, usually the only thing that could actually make two places more meaningfully linked is by information. There's some kind of intangible glue that connects them. Thus, it's not actually a true pointcrawl. It's really just a flowchart of scenes in the plot, slapped on top of a map background.

So in Alexander's system, sites are added to cities on the basis of plot, and he essentially assumes that "whatever reason it is that players are adventuring in a city for probably has to do with wanting to investigate connections between people" …even though I kinda disagree with that. I mean, don't get me wrong: if my game were a mystery thriller about detectives, then this would be very good advice. But it doesn't really help me with shopping, carousing, planning heists, etc.

But he also says that if you want your city to be usable for more than just one investigation plot, with more locations listed than just the handful relevant to such-and-such's criminal conspiracy, then you should create "layers" of node networks. Each layer is a different plot that could be followed. The vampire cult mystery adventure? That's a layer with its own network of locations. The thieves' guild "series of heists" adventure? That's another layer. The slow infiltration of fungus people popping up around the city? That's a layer. And so on. So eventually your city will have plenty of locations, it's just that each one is there because of its role in some specific conspiracy or plot (even if the players don't know which ones are part of which plots).

This is really creative and brilliant because it'll help you generate lots of locations in the city that all have a reason to be put on the map and will guarantee ADVENTURE! if the players visit them. But... I still just can't get on board exactly as he describes it. It's not flexible enough for true sandbox play. While he does allow for 1) a general layer of universal important locations, and 2) ways that the party can kinda "accidentally" jump from a location in one layer to another, likely by making the "wrong" connection in their investigation, this still feels way too built around DM-planned plots. I run a sandbox, and thus, I cannot decide or anticipate why my players would want to go to any given location.

Alexander's system would tell you that: there's a cult hideout that you reach when you correctly deduce the link between them and the children kidnappings happening lately, and by talking to members at the hideout you can also find out that there's also a secret location in the cult's control that you can go to once you find out about the upcoming full moon ritual. For the plot he's written ahead of time that should be fine. But for my plotless game?

I am telling you, if my players go to the cult's hideout, I cannot assume that it must have come from them investigating it for the purpose of answering the mystery of "who is kidnapping all these children and how they can be stopped." For all I know, my players went to the cult because they plan to join. I also cannot assume that getting there must lead to them being further led to the secret location where the cult ritual will take place on the next full moon. For all I know, when my players get into the cult, they're going to use it as an excuse to terrorize every pig-farmer in town as a sick fucking joke. That means I need another route for them to reach the hideout than this child-kidnapping plot, and I need to know, procedurally speaking, how to connect them with the residences of pig farmers they request to go to next, since they aren't interested in the full moon ritual and have no reason to go to the secret location next. The "information network" that connects locations is useless to me because I cannot define what information is meaningful or not.

See how there are districts but then also sites
of interest within each district? They're both
helpful structures, trust me.

5. So then, some other folks have modified the pointcrawl suggestion and instead redefined the "points" as the districts/neighborhoods themselves. A district contains within it a collection of notable sites, and you can move within it in a totally freeform fashion. Just declare "we're already in the merchant quarter, let's head to the Ivory Bank" and boom, you're there. But the relationship of one district to another still depends on physical routes limited by adjacency, so movement between districts is confined to their spatial relationships to each other (like a pointcrawl!). In that case, roll for an encounter each time the PCs enter or exit a district, since those are the lines which define a "meaningful distance" crossed.

"Now we need to get to the Thieves' Guild, which is over in the slums, past the industrial district. Sounds like we might have a couple encounters along the way."

This is so much better! Time passes whenever they move, and within a single district that's nearly always "1 time unit." But if their next stop is more than one district away then it'll take a meaningfully greater amount of time to reach, and might have something interesting happen. A tiny 1-district village? Alright, every location they move between takes the same amount of time (maybe, like, 10 minutes per location). A huge metropolis with 20+ districts? Alright, walking nonstop from Hell's Kitchen in Manhattan to Forest Hills in Queens is going to take a substantial amount of time (in real life, I believe about 3 hours). I'm comfortable with this amount of granularity in an "urbancrawl."

Except sometimes my players are in the middle of a pretty important wilderness adventure/dungeon hopping/megadungeon venture and they have a race against time and they're just stopping in town real quick to buy some vampire hunting supplies and for the love of God I do not want things to devolve into a "shopping session." I hate shopping sessions so much. They eat up so much time and offer me nothing of interest as a player. Roleplaying shopping might be my number 1 most hated activity in D&D, and even for my players who like it, it is firmly ranked as a lower priority than actual substantive activities. So yes, this is a good amount of granularity to play with sometimes. But we need to be reeeaaal careful with just how much granularity is required in our rules.

6. One of the most baffling resources I found in my research, I'm sad to say, was the advice from the Tome of Adventure Design by Matt Finch of Frog God Games. The book is otherwise very good, and even the section on settlements has a lot of really good random tables to use. But it's where he described adjudication of adventures in settlements that I thought he lost his marbles. First of all, he tells you there are exactly three types of urban adventure and then, at least going by how he then frames the following advice, seems to expect that the party will declare which of those three types they'll be doing... at some unspecified point. I guess at the moment they enter the settlement? Don't get me wrong, it's a good practice to ask your players "what are you intending to do while you're in town?" before you start. But, like, he makes it seem like which of the three acceptable answers they give is going to initiate completely distinct and incompatible "dungeon master protocols" for the rest of the session.

Did I mention his three adventure types are also bizarre as hell? One is "exploration adventure" (AKA the players decide to goof around and just wander the city hoping that something cool will happen), which isn't actually very common once your players aren't rookies anymore. Kind of like how you stop doing that thing in GTA where you strip naked and go on a rampage after the first few times because, like, it just isn't a special experience anymore.

Another type is "shopping trips" which nearly gave me a heart attack, but then he elaborated and said that this category also covers getting healing, researching information, and any other non-adventurous activities. That feels a little broad to you too, right? I may hate shopping sessions, but I think it's worth saying something about how you might want to adjudicate each of these activities differently from each other. Like, for example, anything related to downtime in a settlement would fall under this type. That feels like an awful lot.

The third and final adventure type is "mission adventures," which I can kind of understand would cover anything that's an "actual adventure" that just happens to take place in a city. But then his explanation of how to prepare and run this is simply baffling. "Missions normally have two phases: an information-gathering phase and a combat phase." He then goes into detail about how to prep the inevitable combat which apparently characterizes all adventures that'll happen in a city. Really??

These three adventure types seem so unbelievably limiting to me. What if you're trying to recruit followers in town? What if you're playing out a siege battle from within the city? What if you're getting involved in politics and having frequent meetings with politicians and staffers and attending events and arranging bribes and whatnot? What if you're trying to start an underground rebel movement and you need to create and disseminate political pamphlets, arrange a secret meeting, and starting gathering resources for some sabotage against your enemies? What if you have a National Treasure-style scavenger hunt around the city to complete in time? What if you're Omar from The Wire and your day-to-day is going to drug houses, kneecapping drug dealers, and stealing their stash so you can fuel a perpetually itinerant lifestyle of bouncing between the few trusted friends you have in town, while occasionally getting together a squad of like-minded knaves and planning more complicated operations when the serious drama inevitably starts?

Why do so many people writing about "how to adventure in cities" have such poor imaginations for what kinds of adventures you might have in cities??

In a way, the "answer" to how you should create a usable town or city for D&D in a sandbox game is to follow the same logic you do for anything you prepare in a sandbox game: create and provide lots and lots of information. You don't plan for what'll happen. You don't tell the players the steps to follow. You don't try to categorize their actions. You just give information to players and they decide what, if anything, they want to do with it. They'll come up with stuff that'll very quickly break your attempts to structure their actions. The more information you provide, the more they have to work with and, in all likelihood, the more they'll do. The real skill is in being able to know 1) how much information you need to provide for things to be satisfying (since no one likes doing more work than they have to), and 2) what kinds of information is useful and gameable to PCs. This is why providing every single shop in town is unreasonable, but providing a list of 5-15 "special, important, or otherwise notable landmarks" in town is a great starting point. A lot of players will gladly look at that list and say, "alright, I'll bite: let's go to this 'undead labyrinth bazaar' I see next to the river."

7. And that brings me to procedures. I love procedural play and I strongly advocate it in RPGs. I've written a lot about it before and I'll write a lot more about it in the future. I'm trying to create firm procedures for my Knave hack, starting with my dungeoncrawl rules I wrote about here (keep in mind this is outdated, as playtesting has led to some significant changes). But... I feel iffy about applying a procedure to urban play. For a long time it was exactly the thing I was trying to create. I spent such a long time researching distances and walking times and hex sizes I might apply, all so I could make it "crawl"-ready. I tried to figure out the optimal timescale for "turns" and what steps to apply that could be universal. I already listed it in the beginning but basically, my thinking was trying to lead me somewhere like the "city procedure" blog post from Detect Magic. 

This had a lot of promise to me, but I just had to conclude that urban areas are far too flexible for a single procedure to be more useful than it is restricting. Dungeons and wilderness areas and battlefields and sailing the seas and managing a domain and space flights and whatever else all have narrow parameters and specific choice architectures and challenge patterns that lend them really well to a defined procedure. But you could come up with a dozen or two major, deep activities that take place in settlements that could each get their own procedure, and I bet most of them would look pretty different. Obviously, the point of a game procedure is to provide guidelines and not be a straightjacket ("here are some actions you can do, not every action you can do") but I just can't identify enough consistent variables between all the activities I can think of taking place in a settlement for there to be any guidelines leftover. I tried sitting down and thinking of what the universal "urbancrawl" experience entails. I tried making categories of urban adventures like Matt Finch's three types. But I just kept coming up with more and more and more examples that would break it.

Hence, just 1) provide information and 2) see how the players want to use it. I'm not going to have an "investigation" procedure that I can definitively say my players are operating in at a given moment. I will simply recommend a minimum amount of information that the referee should prep per settlement and that players should expect, and then explain that you can always add more if you get to know the settlement better. I gave a little something for movement and some advice for "how to determine how much time X activity eats up" but I otherwise cannot be very detailed. There's a sweet spot for game structures vs referee fiat and for urban spaces that sweet spot involves waaay more referee fiat.

4. First draft of the settlement pages from Brave

Here's the link to the rules. I've included the new pages in here along with a few extra that repeat relevant information already in the base game. But if you really want to see the current draft of Brave as a ruleset, it's on the sidebar of this blog. Whenever I finish making these pages, I'll edit them into the core rules document somewhere (after dungeons but before magic?). To elaborate on this, I need to cover two things. First, I need to explain a bit about my reasoning with what's on these two pages. Second, I'm going to show you the "settlement info sheet" and explain that, with a few examples of settlements modeled using these rules.

On the first point, I want to explain that I try to write things with the intention that both players and referee are the audience, so I rarely direct anything specifically at one or the other. Even things that would normally only be presented to the DM, I try to put in front of players in case they want to see what the DM is seeing and get on the same page.

Also probably of note is that my guidelines still allow for the Alexandrian system to be applied on top, if you're less sandbox-inclined than me.

The main ingredient is the "info generator," so to speak. It's a way to procedurally generate more and more adventure-relevant info. But it can't do all the work for you. The real love and attention should go to making each feature seem unique. For every building, you'll probably need at least 1 NPC. For every tavern, you'll want a fun name and a signature drink. For every specialist shop, you'll want to come up with a few unique and fun items. For every landmark, you'll want something truly special. And factions? Factions are a whole subject of their own, of course. They're the most important moving piece involved.

Here's what I think is important: the right kinds of info are included for faction-heavy play, since factions draw their power from major sources of capital and defensive features, plus they might have influence over specific landmarks and even "districts" and whatnot. But those things can be valuable for lots of other purposes, too. If you fill out the rest of the info for a settlement as prescribed by these guidelines, then that'll give you a pretty good map of what factions have to play with and lay claim over, kind of like the "claims" in Blades in the Dark.

In fact, if you read Blades in the Dark and look at the gazetteer of Doskvol, you'll notice that it's basically just the same thing as I've created here, but if the referee made twelve districts (plus another seven landmarks around the city) rather than my maximum of seven. The way they've written up the city in the core rulebook, you'll find that each district has pretty much the same density and type of information as what I suggest, and uses it as a jumping-off point for flavor to be added.

Something else I think I "got right" is the shopping stuff. See, while I hate playing out shopping as an activity, I do think there's something to be gained by having more depth to shopping than merely providing a list of items and their prices. Limiting item availability by community size is both realistic and it pushes PCs to sometimes travel to get stuff they need. I created the category of "specialist shops" as a concession to allow some amount of fun, memorable shopping with cool NPCs the players might befriend. If a player needs to commission something special, they'll have to find the right specialist vendor for it, which might end up driving them to travel around a bit and visit several different settlements in your world.

As for the parts about navigation, I'm pretty confident in saying that I described more succinctly and accurately the stuff you need to know and understand than Vornheim did. It bothers me how often people neglect to address the most basic action of play: what sentence does the player literally say out loud when they do stuff in a city? The answer to this matters. Many of the urban adventures/settings I found in my research just said "when in town, players choose one of the ten landmarks to decide where they go" like that's really a be-all, end-all solution.

So if merely having a dozen or so sites is insufficient, then how much more detail do you need? My co-writer described it to me like this:

If the players are in the woods, you can just say "there's a bunch of trees" and that's acceptable. That's as much information as they need in order to know what to do there. But if they enter a town, you can't just say "there's a bunch of shops" and leave it at that. Nothing is ever "just a shop." The player needs to know what any individual shop is in order to know how they interact with it. The specific answers make the difference between whether or not they feel it's worth their time to interact with those shops or treat them as background color. But you also didn't say "there's a shop" which they could choose to go to or not. You're offering "a bunch of shops," and you'd have to provide that level of info for all of them. That's an unreasonable amount of work.

My solution is to this problem is to split the difference. On the second page I offer the "generic locations" list that players can always fall back on. It's a manageably-sized list of sites they know will always be present. That right there is the implied "detail" that hides behind a broad description like "there's a bunch of shops." The players know in their heads that when I say something like that, it represents the kinds of results which are on that table in the rulebook. That way, I can get away with just saying "there's a bunch of shops" without needing to go into further detail about any of them. And if, say, a fight were to break out on the street and the referee needs to quickly set up a little chunk of city with some buildings around, then they can pull from that list for generic locations.

Contacts are a simple little mechanic I added because I think it's the kind of "toy" that players enjoy being handed to play with. Sure, you could just instead say "a 'contact' is an NPC you've met before and can reach out to. Don't overthink it." And indeed, all previously-met NPCs are contacts. It's not an actual formal status in the rules. But the reason I have this mechanic anyway is because sometimes the PCs just haven't met enough NPCs yet in their adventures. Or they haven't met the right ones for what they need, even though the idea of "asking an NPC for help" seems like it should be validated. So I wrote a small rule for it. It's this kind of thing that gives players ideas about what sort of stuff they can attempt to do. And, to an extent I rarely ever go, it allows them to have a small hand in "creating the world" when it's helpful to them.

The "Lay of the Land" section is pretty important because it gives you a method for delivering information. After all, we've established that 1) referees need a way of generating plenty of adventure-relevant info about a settlement to adjudicate sandbox activity, and 2) players need access to adventure-relevant info about a settlement to engage in sandbox activity, but knowing how to best get the information from the referee side over into the players' side is not as obvious as you'd think. After all, players are empowered by knowing info about a dungeon before they go in, like what kind of monsters are there, a history of how it was built and what it was used for, the modus operandi of the wizard who currently runs it, and so on. But you probably don't represent their research by just handing them the dungeon map and room key. Maybe a blank or incomplete map if they're lucky, but not that much. You typically just give them a few key pieces of info. So once again, I figure, "let's split the difference." Have a way to give them some info to start with but make them work for the rest of it. If they ask, "can we just talk to a local to get a good overview?" then have a simple rule for how difficult that is/how much time it takes. If they're a smarty pants with a high Intelligence score and they want more prior information then have a rule for that, too. But they only have so much control over what they learn about. They can't ask specifically if they know about the library here, they just have to ask for "landmarks in general" and then the referee chooses which landmark they'll hear about. That way the referee can exercise their discretion over what stuff to keep secret if need be. Stuff the players can only discover through adventure.

Lastly, I think the biggest difference between what I offer here and what's been offered before is that I tried pretty dang hard to ground my stuff in a Medieval European context. Of course I expected stuff like Blades in the Dark and Magical Industrial Revolution to be inspired more by Victorian London than anything pre-modern. But I was kind of shocked that, like, everything was so modernized. Games that felt like they should have been "medieval" had a surprising amount of industrial-era features baked in throughout. Making the list of "generic locations" was way harder than I thought it would be because I had to do actual research instead of just stealing lists from other RPG products. None of them would have been "accurate" if I had. A lot of the locations on my list of "landmarks" are things that other games would have put in their "generic locations," because nowadays we take for granted the ubiquity of hospitals, prisons, courts, and libraries even though they were all once very, very rare.

The second thing I need to talk about is how you actually use those two pages. See, what I imagine ties this together is the settlement "character sheet" which you can see filled out with a few examples below. The referee has a copy of one of these for every settlement, and if the party starts interacting with a settlement significantly, then they should be handed an incomplete copy. There's a master template for villages and a master template for larger settlements, but ultimately the referee will need to write out the "location key" on their own.

Here's some examples of how you would fill out a settlement sheet, which you should examine closely and compare against the 2 pages of "settlement rules" I linked above. I think it should help illuminate how you're meant to apply those guidelines. I'm gunna show two example villages (using the village sheet) and one example city (using both the settlement sheet + site key from the referee and the accompanying incomplete settlement sheet for the PCs).

The first village is this one I created using the generation rules that's called Dorothea.

Following everything the guidelines said about villages, I gave it as much info as prescribed and used the random tables to fill in a lot of the details. Other stuff took some creativity on my part but I don't mind. I liked everything I came up with for this village, and I think you could get a lot of mileage out of it for a while.

For the second village, I decided to attempt to recreate a classic with my sheet, the frontier town of Phandalin (from several D&D 5E adventures, but most notably The Lost Mines of Phandelver).

Now, if you're familiar with Phandalin and the adventure it comes from, you'll likely notice that this sheet doesn't include every piece of information about the town. But I think that kind of supports something I've already said: "As a rule of thumb, more info is created for settlements if they are large or if they are interacted with frequently." You're expected to spend 4-5 levels worth of adventure in Phandalin at least, so you'll inevitably want to expand on this starting sheet. You'll eventually need more to work with, plain and simple.

But if, on the other hand, you have 5 or 6 or 7 villages like this in your setting, and the PCs' adventures keep them moving around the world quite a bit, then this amount of detail for each is more than enough. And I think this was a successful test to show that my system can pretty decently model settlements that weren't created with my guidelines, in case you want to convert some settlements you already have into this type of info sheet.

Lastly, here's a city I've generated called Visbelot. I knew going in that I wanted it to revolve around a big clocktower, so I made that decision on my own and then let the generators start filling in the rest. All the following images should be opened in another tab/window to view in detail, although here is a link to a single PDF with all these pages, and here is the link to the diagrams.net file if you use that app like I do. I recommend it.

First, here is the front and back of the main info sheet for the referee...

These should act as a good reference sheet for the referee during play to always have some quick info to pull from. And as you can see, I recreated the "Shopping Info," "Lay of the Land," "Generic Locations," and "Lodging" bits from the rules directly on the info sheet so you wouldn't have to cross-reference the rulebook all the time. Because this is such a large city, as I was creating it I realized that having "settlement-wide factions" would be a good addition, rather than just district-specific factions everywhere.

Here's the map:

I snuck a note in there about district-to-district movement rate for active time but it's not a hard and fast rule. As you can see, I made this quick and easy in MS Paint after mocking it up on paper, and didn't feel the need to include street layouts and buildings I'll never need. That said, I figured the scale couldn't hurt.

This city in particular is strange as hell because out of the many defensive features I rolled, somehow none of them ended up being a wall. Instead, it's got a strange layout designed around a bunch of other types of defense, and I had to come up with a good fluff reason why such a large city for this technology level would somehow not have a wall. And I think it forced me to be creative and give it some character.

Here is the accompanying map key:

And finally, here is the front and back of the "player copy" version of the first info sheet. You can see that I give away a good bit of overview info for free, but then have the "details" of the districts left as blank boxes to be filled in using the "Lay of the Land" mechanic. Then of course, the back is for them to take all the notes they need. I would probably also give players a copy of the map, even if they don't yet know what all the numbers on it represent. They can label the numbers themselves whenever they learn what one of those locations are.

So when the players enter town, I hand them a copy of this sheet, give them a minute to review it together, and then jump into the Lay of the Land rules to let them start filling out a bit of preliminary details in the boxes from whatever background knowledge their PCs have. And I'll describe the coat of arms and have them draw it themselves on their copy because that's fun.

So as you can see, this one ended up being fucking huge. It just happened that I rolled the maximum number of districts possible. While I really like the final result and I think I'd love to play in this city for a good long while, it's a bit concerning. Is it just going to be a reality that all cities take 6 or 7 pages to list their useful info? And all towns will likely take 2 or 3? That wasn't exactly my expectation, but I guess it makes sense. Most medium-sized or large-sized dungeons need a separate room key that has full descriptions of what's in each room, beyond what you can see on the page with the map. Thus, properly preparing a settlement as a site of adventure is equivalent to preparing a dungeon, right? And failing that, the basic rules and info (e.g. shopping guidelines, generic locations table, lodging, etc.) are all sufficient for a settlement you aren't going to adventure in, so a full map and map key won't be necessary if the PCs are just passing through.

So in conclusion, these took me a surprisingly long time to make (mostly that city, not so much the villages), which isn't great. I actually outsourced a lot of details to friends (which was fun!). But then again, sandbox prep is always heavily front-loaded, and I'm glad that I at least now have a system to guide that preparation rather than just randomly preparing whatever parts of the settlement I feel like. I put enough work into that city that I now basically have to use it. But if everyone took this template and made just one city like that, we'd have quite a collection to share, wouldn't we? Heck, even if just 5 people took the small, one-page village template and made one of their own, that'd be a ton of content right there for a small campaign.

5. Why do I care so much?

Maybe this is unnecessary to explain, but the appeal isn't obvious to everyone. I've gotten a lot more pushback against this than I expected.

Just having that basic settlement template, in my mind, will automatically boost the moment when the PCs reach town and have to declare what they're doing at the end of the session. It's not a lot by itself, but having any kinds of guidelines at all tends to be better than nothing. I lean heavily towards minimalist games but I feel that too many of them make a lot of their most minimalist decisions out of laziness more than anything else. I have played city sessions that were improv'd and no, that isn't the best solution for every activity outside of the combat and magic rules, guys.

But even for those who'll accept a city template if you offer one, I feel like a template to merely generate generic settlements is a bit unsatisfying to me. I don't think you necessarily need rules to support it, but you should at least encourage the DM to come up with memorable gimmicks to the town. That's the key to making this click. In my rules I suggest a minimum amount of information to provide that PCs can work with, but spice up your town, please.

See, I love cities in real life. I love how each one seems to have its own character that everyone knows. I love how Rome has ancient Roman shit everywhere and is on 7 hills + the Tiber river and it has the colosseum and arches and the forum and the pantheon and a theocracy city-state within the city. I love how Venice is a lagoon city built on water with canals and gondolas and it's all sinking. I love how London has the iconic courtyards between each building and it's always raining and there's a big river running through. I love that Washington DC is a government town but its heart is the black community and immigrants, and it has a ton of monuments and there's a mandated low-skyline for all buildings so the monuments aren't visibly obstructed, with the Smithsonian museums available for free and an amazing world-class arboretum too. I love Havana as this awesome port town built around Spanish fortresses and palaces and with a vibrant community of graffiti artists, all the buildings pastel colors and everyone driving 50's cars while they desperately try to sell you cheap shit. I love how Prague has the fucking spookiest architecture on earth and some kind of ghost story or vampire legend associated with every building, bridge, church, shop, etc. in the entire city, plus an incredible astronomical clocktower and a synagogue that's said to house a golem, plus three historically important instances of defenestration in its backstory. I love weird physical setups for cities, like the iconic cliff dwellings of the Pueblo, or how Mexico City started on an island but then they just built a city on top of the surrounding lake. I love strange Hong Kong or Singapore. I love Monaco and Casablanca and I love New Orleans and Bruges. Jerusalem and Istanbul and Baghdad. I've never even been to nearly any of those places but the handful of iconic unique traits they each have are fucking rad.

I love Minas Tirith, the City of Kings, from Lord of the Rings, with its incredible white mountains and citadel. I love that Markarth in Skyrim is built atop dwarven ruins and everyone's house is either a cave or it's carved into the mountainside. I love that Vornheim is more vertical than lateral, with the default unit being "tower" and there being hundreds of bridges connecting the layers of the city. When I was a child my favorite book was Bone, the comic by Jeff Smith. And my favorite part of Bone was the 8th and 9th books, because they took place in the capital city of Atheia and contained

shit like you see to the right. I love Clock Town from The Legend of Zelda: Majora's Mask and I love Lankhmar from Fafhrd and the Gray Mouser and I love Mos Eisley in Star Wars and I love Gotham City from Batman and I love Sigil from Planescape and I love Monte Cook's Ptolus and I love pretty much any flying city in anything ever.

It is absolutely fucking bananas to me that someone would really think that "D&D isn't meant to take place in cities." Meanwhile, for those who agree with me enough to set their entire campaign in one of these incredible places, I respectfully ask "why not fill a kingdom with them?" and let the players choose where they visit, why, and what they'll do in each one. Not to mention the incredible joy and satisfaction that can come from players wanting to build their own settlement, slowly investing in upgrades and defenses and having a tight-knit community and getting to decide their own quirks that make it a memorable and unique place.

When I read about cool cities with weird features, it really inspires my worldbuilding brain. I have a major city in my campaign based off of Nördlingen in Germany, one inspired by Houska Castle in Czechia, and one that's inspired by Civita di Bagnoregio in Italy. Because how could I not? That's the stuff of true adventure, just as much as the wilderness and the ruins of dungeons.

-Dwiz