I've changed the dormers for you, Wyvern :)

These appear only on the larger houses in the set - the richer merchant style houses. I'm just testing them on the only tiled house I've made so far, which is the smallest one.

Remy's suggestion is a good one, but maybe (and this is only a maybe) you could tackle it the other way around - make the mountains first and then a soft edged pass between them, a bit like drawing a river in the lowest point?

Do you have City Cliffs - the 2020 Cartographer's Annual? Not a problem if you don't, but if you do you could use the cliffs as rocky bluffs a bit like this. (Sorry about the crude 5 minute drawing).

These are city scale cliffs, but if you use them more as rocky bluffs at dungeon scale (I assume it's a dungeon scale map you are making) you could build up level on level - maybe use different rocky textures instead of grass.

Another idea is to add a sheet similar to the one in SS5 with a hugely blurred Bevel, Lighted effect on it to draw transparent polygons on it for hill shading. I've got one here in the style I'm working on.

You could use a combination of both those things, or combinations of other techniques, but the main suggestion here is to start with the terrain and not get stuck on the path itself. That can be added at the end when the terrain is done, and might even be a result of the terrain, rather than having to be specifically drawn in as a path.

Having fun with different kinds of dormer. This is the same basic building...

Something a bit like this, then... Or is this too melted to go with the thatch?

Oh shoot! I forgot to cut the chimney extent out of the map file, so its a lot brighter than it should be, but you get the general idea.

On the progress side (or lack of it today) I've had quite a struggle getting the gradient shading of the map file correct so that the hollows around the dormer look filled with snow, and everything the right size and shape to be the same as the original but with a layer of snow on it. Not sure how all this is going to work when I start combining them, but we'll see in the morning now.