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.

Well, I had a go with combining what I did with the original tiled house. It's not great - mainly because the map files are quite different and the combination was a crude mask that erased some of the snowy version and its map file to reveal the original house underneath it. The map file for the tiled version is very steep. The map file for the snowy version is very shallow - so that the snow doesn't bleach out to being completely white all over. There are a few strange patches you can see on the darker parts of the roof to the south where the resulted blended map file is neither one thing or another.

Let me know what you think.

@JulianDracos - I live in an area with plenty of thatched buildings, and since thatch is one of the greenest roofing materials available that isn't likely to change very much. It is also about 10 times more insulating than tiles unless you have excellent insulation in the attic space of a tiled house. So the snow does tend to stick and stay much better on thatched cottages than it does on tiled houses. It's therefore not inconceivable that you would get some wind erosion of the snow on tiled rooftops and/or melt off. The tiles are warmer because they don't keep the heat in as well as thatch does.

The other question I have is: does the snow melt into tidy sharp-edged patches, or is there a blend like I've created above where the snow shades out gradually into a melted patch?