Arrowfield [WIP]

[Frenchie the DM]

It's an interesting city but I think the overall texture is a bit harsh. It makes the outline of the guild district buildings harder to make out. Maybe made a bit subtler so it doesn't dominate the image so much. Also I think your land/hill contours might have a bit too much white in them. Might be worth changing it to light brown instead.

I approached this first with an oil painting filter, which made the rivers look quite nice, but overall detrimented the texture. I applied a basic Gaussian blur: 1px radii. For now, I removed the contours, and will approach them again when I'm going through finishing. Thank you!

The annual battles make me assume that the city would slowly divide itself with inner walls

I tried this, and I think it will help me "solidify" (maybe not the right word) workflow of the buildings.

Here's the NEARLY COMPLETE first district: Uptown. Also new walls.

 

The new array of central walls protect an area called the Bullseye, a central nexus for trade and communications. (Also the location of possibly Aboleth mind-control devices, hoards, and various merriment.)

Now, I've marked out the specific districts:

 

Yellow is Uptown: A district defined by the Lone Man's Theatre and it's prime land-importance. It is also the holding ground against ground assaults.
Navy Blue is the Guilds District: A conglomerate of crafting and financial interests, most likely controlled by scheming entrepreneurs and filled with opportunities for buying ships, airships, and/or funding the downfall of the city.
Pink is Cliffside: An aristocratic riverfront array of properties - hidden lust, blood feuds, and plenty of hor d'ouerves.
Purple is the Lord's Land: Land dedicated to Bowyer Castle and the Riverwatch Citadel - power centers of the fief and city.
Green is Bull's Center: Centered around the Bullseye, along with the Cathedral of Saint Baptise.
Red is the Slums: Perhaps when the mind-control is lifted, a religious revolutionary emerges in the dirty back alleys of the city.
Teal is the Docks: Maybe a cult of necromancers was paying off the sailors a pretty penny to keep up shipments of the tainted waters - once it's gone, they'll be looking for skulls to crack!

Thoughts on the entire worldbuilding aspect and implementation are much appreciated, and thank you all for your input so far!

[Sushipopsicle]

Now, I've marked out the specific districts:
Yellow is Uptown: A district defined by the Lone Man's Theatre and it's prime land-importance. It is also the holding ground against ground assaults.
Navy Blue is the Guilds District: A conglomerate of crafting and financial interests, most likely controlled by scheming entrepreneurs and filled with opportunities for buying ships, airships, and/or funding the downfall of the city.
Pink is Cliffside: An aristocratic riverfront array of properties - hidden lust, blood feuds, and plenty of hor d'ouerves.
Purple is the Lord's Land: Land dedicated to Bowyer Castle and the Riverwatch Citadel - power centers of the fief and city.
Green is Bull's Center: Centered around the Bullseye, along with the Cathedral of Saint Baptise.
Red is the Slums: Perhaps when the mind-control is lifted, a religious revolutionary emerges in the dirty back alleys of the city.
Teal is the Docks: Maybe a cult of necromancers was paying off the sailors a pretty penny to keep up shipments of the tainted waters - once it's gone, they'll be looking for skulls to crack!

I've got some general questions/comments that thinking about might help you with your worldbuilding aspect. I'll break it down by color for ya.

Yellow/Uptown - This one is particularly interesting to me. I see two ways this land can develop over time, as it's the closest to the large skirmishes. 1) It get's overrun with fighting year after year and eventual ware and tear slowly make it just as bad as the slums. This could be where those rundown mansions you mentioned earlier reside. Also, a lot of people would probably leave their older-style homes in this part of the city, buy cheap land in the original "slums," and start pumping money into their new neighborhood instead. This would allow you to have clearly contrasting architecture between the "old" and "new" as the players walk from district to district. This would mean Uptown has taken a downward turn, and the slums would likely be on an upswing (or become even worse as it slowly overpopulates).
Alternatively, 2) The residents double down, pumping tons of money into that part of the city to beef up security and protective. More guard patrols, better quality walls along it's borders, and likely a larger sense of city pride from the resident population with each successful assault protected against.

Navy Blue/Guild District - Do you know what guilds reside in the city? Could a PC potentially join one of these guilds?

Pink/Cliffside - Is the coast along Cliffside an actual cliff or just a name? If a cliff, how steep of a drop? Are there rocks below? Could a PC survive the fall?

Red/Slums - Revolutions can be fun (And see my notes about Yellow/Uptown).

Teal/Docks - Who/what holds the largest monopoly over the docks? Is it a political figure? Is it a guild? (It could be a political figure giving his guild large tax cuts when using the docks) If you do want to go down this necromancer route, were the necromancers working/being controlled by the Aboleth, or do they have their own sinister plans and saw the chaos the Aboleth was causing as a good screen for their operations?... Ooooor whatever else you come up with.

[Frenchie the DM]

I've got some general questions/comments that thinking about might help you with your worldbuilding aspect. I'll break it down by color for ya.

Yellow/Uptown - This one is particularly interesting to me. I see two ways this land can develop over time, as it's the closest to the large skirmishes. 1) It get's overrun with fighting year after year and eventual ware and tear slowly make it just as bad as the slums. This could be where those rundown mansions you mentioned earlier reside. Also, a lot of people would probably leave their older-style homes in this part of the city, buy cheap land in the original "slums," and start pumping money into their new neighborhood instead. This would allow you to have clearly contrasting architecture between the "old" and "new" as the players walk from district to district. This would mean Uptown has taken a downward turn, and the slums would likely be on an upswing (or become even worse as it slowly overpopulates).
Alternatively, 2) The residents double down, pumping tons of money into that part of the city to beef up security and protective. More guard patrols, better quality walls along it's borders, and likely a larger sense of city pride from the resident population with each successful assault protected against.

Navy Blue/Guild District - Do you know what guilds reside in the city? Could a PC potentially join one of these guilds?

Pink/Cliffside - Is the coast along Cliffside an actual cliff or just a name? If a cliff, how steep of a drop? Are there rocks below? Could a PC survive the fall?

Red/Slums - Revolutions can be fun (And see my notes about Yellow/Uptown).

Teal/Docks - Who/what holds the largest monopoly over the docks? Is it a political figure? Is it a guild? (It could be a political figure giving his guild large tax cuts when using the docks) If you do want to go down this necromancer route, were the necromancers working/being controlled by the Aboleth, or do they have their own sinister plans and saw the chaos the Aboleth was causing as a good screen for their operations?... Ooooor whatever else you come up with.

A discussion of my world AND mapping? But Sushipopsicle, it's not even Christmas.

I enjoy the alternative for Yellow, and think it would be a nice introduction. The closer to the theatre, the more you get into the "Thespian / Bohemian" zone. The idea of a fusion and conflict between fervent city pride and theatrical expression intrigues me. I definitely want to do a riff on Phantom of the Opera with the Theatre.

Cliffside was actually named for being next to the cliffs that Bowyer Castle rests on - but I think you're geographical idea is much better. Clearly Arrowfield is a location of oddity, and nothing screams odd like a cliff top city among some plains! Oh yes, it's defensible and everything! Hell, the mines can just be inside the cliff itself. Oh yes. This geography is far superior!

Hijinks ensue! Public executions by being pushed off the cliff, parties of the elite at the edge, potential city-wide collapse if the mines fall in - oh yes. My sinister-DM-mind is in overdrive.

I've just had a revelatory moment. But, onto mapmaking. This change now means that near all traffic enters through the front gates. No more dedicated docks, it would seem. (Docks would also dry out due to the tainted river waters, no one wants to go upstream to it.) The idea of a group profiting off selling the water (and thus my players having some motivation to perhaps keep the corruption going) will probably be relegated to a guild, then. Which is not hard. Perhaps the now defunct Miner's Guild is still oddly profitable... hmmmm...

Will post results of my progress soon. Thank you for your inspiration Sushipopsicle!

[Frenchie the DM]

Okay, penned out the Guilds district. Also made a basic shadowing, but I'll need to adjust the lines of the river (or perhaps something else) to demonstrate the cliffs... frankly I don't know how to do that. Side view graphic, maybe?

 

[Sushipopsicle]

A discussion of my world AND mapping? But Sushipopsicle, it's not even Christmas.

I enjoy the alternative for Yellow, and think it would be a nice introduction. The closer to the theatre, the more you get into the "Thespian / Bohemian" zone. The idea of a fusion and conflict between fervent city pride and theatrical expression intrigues me. I definitely want to do a riff on Phantom of the Opera with the Theatre.

I'm glad I was able to get your juices flowing! I'm definitely more accustomed to roleplaying and storytelling aspects than I am mapmaking, so I'm not really sure how to address expressing the elevation. The simplest solution is sometimes the best, in which case I would just inform the players verbally. But if you want to express it on the map, contours like what you had earlier with Crow's Hill (I believe that's the name) would probably be best.

I'm also glad you went with the alternative for Yellow! While both could make for an interesting world, the first option felt kinda monotone and almost dystopian. This one shows that the city is still very much alive, if somewhat odd.

No more dedicated docks, it would seem.

You can still have cliffside docks if you wanted. The goods could just be lowered/raised by a pulley system or maybe carried up on mules through a spiraling tunnel. It's your fantasy world. Heck, you could have guild wizards levitate things up and down for a living! I can't imagine a city with so much water around it not utilizing that feature at all.

I really like the style for this map. I just finished a world map and am now moving into specific cities and villages within the world - I'll probably steal some design aspects from your map. Is there a particular tutorial you've been using or is the design all out of your own head? What software are you using?

Also thanks for the rep!

[Frenchie the DM]

I've kind of been pulling from a variety of tips and tricks from this site. I'm currently using Photoshop CS6. It's primarily just using the pen-tool to lay out selections, filling them with black, then applying a drop shadow, color overlay, texturing pattern, and a single 1px black stroke internally. That's all in one layer. I then use another to apply a striped pattern at about 50% opacity.

Then it's just testing and trying to see what works. The walls are done in this same way, with gray fill instead of black. Design principles are pretty much try not to make it look like it breaks the laws of physics. Unless it's in the Mages District - then do so.

[GreatWhiteNorth]

Overall I like how it's coming together, though I agree with previous posters. I think you can achieve your grungy hijinks feel with a more subtle texture. The city streets and buildings look great! One concern about the aqua-colored building: I'm not sure exactly how the balls are functioning. Buildings usually aren't that sharp.

[Frenchie the DM]

Howdy, bit of a return from a short break / delay!
Introducing three more districts, these are actually quite different because they are polar opposites of the scale of the rest of the city: the Mega-rich Cliffsides, the Docks, and the Slums. I'm not quite satisfied with the implementation of any of them, but there is a certain time crunch as I approach my next session coming up. I understand the glaring... largeness of the Docks and Cliffsides, but this was intentional. A second pass is probably necessary.