Next round of maps, will most likely clean up the thread in the near future so all the maps are on the top post. All Duchies of Wayside are now complete except Gatik (which is a city state and quite small) and the Isle of Ca La Dorne aka Thonesh...
It depends on how detailed you want your map and how much skill you have with pen and ink. Paint is a good option and it is free, as it is included with most Windows PCs. Gimp is the open source version of Photoshop. I have used Campaign Cartographer in the past but, I purchased that program.
What were you thinking and looking for?
If you're not much of an artist Inkarnate has an easy map-making website with a good number of free assets...it's not as fun (nor does it look as nice) as drawing my own but it's good for quick work that still looks good.