Welcome to the Guild Lielac. Try to take a look at the Tutorials section. WIP section can be interesting since you can learn frome other's workflow.
I found out about this site when Tarn Adams (the creator of Dwarf Fortress) mentioned that this month's mapping challenge here involved DF maps. Since I've got a dabbling interest in maps as a creator of fictional worlds (which then need maps - or actually, more usually I draw the map and then make up the people that live there), I figured I might as well join up and look about for tips on how to draw the things so they look natural, either by hand or using software.
So. Can anyone give a dabbling cartographer, who mostly likes mucking about making random maps for the fun of it and isn't very good at it yet, any pointers?
Welcome to the Guild Lielac. I'll third the suggestion to browse through the tutorials. If you don't yet have any digital software then you may wish to start with GIMP, since it is a pretty powerful free program, and is well supported in the tutorials here.