While there were conversations about this in the past, those were much more generalized. Now, I personally don't have issues creating world maps, regional maps, or 'battle' maps, as it were, but...
While there were conversations about this in the past, those were much more generalized.
Now, I personally don't have issues creating world maps, regional maps, or 'battle' maps, as it were, but when it comes to city maps... I'm consistently at a loss. That said, I don't want this to just be me begging and whining into the void about how I can't find something that I prefer to make city maps in, so here's what I've used and would recommend over the past 15 years or so:
Of these, I definitely recommend Wonderdraft the most. I think if you put in enough time and effort, Photoshop can turn out better (and most detailed), but if you're interested in a style that Wonderdraft has support (and assets) for, it's pretty much perfect. It's a one-time cost, has been getting consistent updates and support since it was in beta years ago, and the community assets are pretty much unending. The one caveat to Wonderdraft is that if you want to make an absolute behemoth of a map (like I'm apt to do), it will eat some serious resources and can begin to lag, due to how it handles each individual tree/mountain/path as a singular, editable asset.
Campaign Cartographer is an oldie that I tried about ten years ago, had some success with (mostly in how it designed continent outlines and things), but just didn't feel like it had enough malleability to create things the way I saw fit.
- Region/Continent Maps: Wonderdraft, Photoshop, Inkarnate
I think everything I said about world maps applies here, as well. I haven't used Inkarnate in the better part of a decade, but I know the free version was very limiting and there were some concerns about the company 'owning' anything you created in the program. That said, a brief look at it now makes it look like a more closed-off version of Wonderdraft, but with a subscription instead of a one-time purchase.
- Battle Maps: Dungeondraft, Photoshop, a plethora of generators that I can't even begin to remember dating back 10+ years
Before Dungeondraft, I pretty much hated making maps for combat. Early in my GMing 'career', I would just have a blank canvas on Roll20 and draw on details as it was needed, and eventually I just pivoted completely to theater of the mind for all of my combat. And then Dungeondraft rolled around, and it was pretty quick to export from there, incredibly quick to import to Foundry (with a module), and Just WorkedTM. Before that, I did occasionally try and make things in Photoshop, and would follow tutorials from time to time, but it was all just so time-consuming, and with a lot of asset hunting if you wanted consistent art style and detail to what you were doing. It was just so much.
Which, of course, brings me to...
Ah, the problems. So, I tried to make city maps in Wonderdraft, but it's very obvious that it was built for a larger scale, and there are a lot of 'hacks' (or workarounds, I guess?) you need to do to make it work, and it can be frustrating and very time-consuming, as there's nothing there to really automate the process at all. For example, Wonderdraft has this beautiful 'paint brush' for assets such as trees or mountains that will 'spatter' them across a set radius, with a set density, etc. This is very helpful for something random like forests, but essentially useless for placing buildings. Dungeondraft is a little better in this regard, but has the opposite issue: Everything is too 'small' and focuses on more grid-based, rigid design, given that it's built for, well, dungeons. And battle maps in general.
I purchased City Designer 3 (along with a big pack of Campaign Cartographer add-ons) as part of a Humble Bundle a while ago, and I kind of enjoyed it, but it really felt like the amount of effort required wasn't worth the end result, which - at best - would be using art assets designed to give the feel of the maps from D&D 5E. And even then, that limited the asset options because it didn't seem like there was a lot of additional third party support for the program (which is definitely showing age). That said, it's the only one I've used that seemed able to handle good building placement along roads, able to do it automatically. That said, Photoshop?
Probably the best time I had making city maps. I had to stylize them, but with enough ingenuity, good knowledge of automation (through recording Actions), and following some art style tutorials, you can make a "cheap" city map that's able to have a lot of variation. If you're interested in map design in Photoshop, I highly recommend the tutorials of Jonathan Roberts, who is very much my 'gold standard' for map creation. Unfortunately, he doesn't really update his site any more, and some of the tutorials show their age, but all of the content there is still great.
Then, we have generators. The ones linked above are the best ones I've found, though the city ones leave a lot to be desired as far as graphics and specific details go. But the village generator for small towns and the like? Beautiful. It's genuinely just a perfect little generator if you don't care all that much about the specifics of the map. So, for most towns and villages, it's fine. But what if it's a town built up against a mountain, that sprouted up around a mine? Well... that's not gonna work. What if it's a town that's split on two sides of a river, protecting passage? No such luck. A swamp town, or one in tree-tops? No, not really gonna work all that well.
And just last year, I was turned towards AI generation here on tildes, thanks to @atomicshoreline and his fairly extended description of how to set things up. But, I eventually gave up bothering him after my old video card kept having VRAM issues with only 8GB.
I have seen some very good city maps made in Inkarnate, but I don't know that I'm interested in something that has a yearly subscription, and I can imagine it being very frustrating long-term to invest in something that I've seen issues with in the past.
So, all of this is to say that I really enjoy making detailed content for my world, but I've always had issues with cities. There's just so much content that needs to be hand-placed in almost every program, and even an un-finished city has taken me well over a hundred hours in Dungeondraft, and that was with me still actively hating looking at it..
So, if anyone has other suggestions, I am quite literally always searching for new ways to make city maps, and I've tried just about every suggestion given to me at least once, often to the detriment of my bank account.
Oh, if someone can think of a better title to this post and wants to change it, please be my guest. I just wanted to contribute my knowledge and recommendations, rather than just throw a "give suggestions" post out into the ether, and wasn't sure how to phrase that.