This is really lovely. My only ever-so-slight feedback is that my old eyes are finding it a little difficult to read the legend, so I would consider increasing the opacity of the background fill/color slightly.

This is a different approach than what you’re asking about, but possibly with the same end result: Remy did two tutorials showing how to construct rail tracks: Martian Mines and the Silver Mine.

Yes, I did use the draw tools for the trees - worked great! For the river, I used "Change like draw tool" to change it to the 75-foot river. I also used the "Change like draw tool" for the sea (the straight closed polygon water tool), the three main roads, the round towers, the square gatehouse towers, the docks, the parks, and the buildings. I used the draw tools (but not the "Change like draw tools") for the city walls, the bridges, the trees, the darker grass beneath the trees directly to the south-east of the castle, the fields, the hedges, the dirt roads, the town square, and the forest on the north side of the map. For the heraldic symbol, I did as you advised, moving the components to the appropriate sheets and changing to a solid color. (Interestingly, the deer didn't fill in completely, just the outline.)

There were some minor issues that had to do with how Watabou exported the data. The river was in multiple sections, broken by the bridges, and the stretch between the final bridge and the sea wasn't there at all, so I did that part using the draw tools. The major road coming in from the west continued up the river a bit, so I had to trim off that part. Same with the road coming in from the south: it continued down the river from where I put the wooden bridge. So you just have to pay attention to what's being changed to make sure the right things are being changed properly, knowing that you might have to trim a bit here and there, or use the drawing tools to add a bit.

But overall, worked great! I am going to do a larger town now, and will time it to see how long it takes.

I've played with a few different options. Thought I could copy the Random Street buildings to a sheet below and then turn then into a gray polygon, but if there's a way to do that without it being a gray house, I haven't figured it out. Tried the colorize effect to mute the effects of the background. Of course, I could delete the background terrain and redraw it around the houses, like for backyards.

But I think, since it's such a small map, that I will just limit the Random Street houses to a few around the paved plaza, like they are specialty shops or government buildings, and then hand-place the rest with the buildings symbols.

Hi Reddog! Welcome.

I'm pretty new here myself — though I’ve owned the software for many years, it’s only been about six months since I realized I couldn’t learn it simply by experimenting. The tutorials really, really helped me.

I’ll let others with more experience guide you, but my two cents: it sounds like Dungeon Designer will best achieve what you want. The name implies old-school D&D dungeons and caverns, but it's really great for any type of inside or outside floorplan (a house, a temple, some crypts, a section of a forest road where bandits are lurking to attack). If you want something that you can use figures on, whether to print out to use with miniatures or to use on screen with a virtual table top, Dungeon Designer will probably suit you best.

As for tutorials, which is how I learned: the new ones are great but I would start with some of the older ones to get the basics down. On the Video Tutorials page, you'll find a really well organized list. I started with Joe Sweeney's, which did a great job starting with the basics. They are old, and some tips have been superseded by software advancements. (For example, Joe made a point in the older videos of talking about placing symbols from the back and moving forward, but now there's a "Sort Symbols on Map" function that makes that advice no longer necessary.) But they really helped me get the concepts down.

The Learning CC3+ videos will give you a good grounding in the basic tools. I would then proceed to the Quickies section. With the Campaign Cartographer Concepts and Blog Videos, I would recommend going to specific ones once you've got the basics down and have a specific question about a technique or tool.

The Live videos are really great, but each one covers lots of different techniques, and many of the newer ones assume some basic knowledge, so I wouldn't start with them. Once you've gotten the basics down, you might want to look at the names to see if there are some tackling stuff similar to what you're doing. For example, if you're designing a dungeon, "Creating dungeon with the Jon Roberts style" and "Livemapping: Dungeon & Cave" would be useful. I've gone through almost the entire archives of Live videos and I learn something from every single one, but you'll want to have the basics down first.