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I don't think you'll like the answer. I manually painted each contour on a vector software (illustrator, inkscape is free and should also work). AFAIK there's no other way to do it. The trick is to lay out mountains and rivers first, and to set up the contours according to that. To see the shapes of the mountains I kept Google Earth open on the side to check consantly. I set down paths that matched the ridges and then paths that matched the rivers between each ridge. Then I placed the contours, contracting them when meeting a river and expanding them when hitting a ridge. Studying contour maps is also useful if you want to do it this way, the David Rumsey map collection has a few.
Hi, sorry it took so long to answer, I often take long breaks between maps.
Hey Portland! Thank you for the kind note. That was really nice to hear today. I will definitely be showing more of the Cladonia style in the future; it's my favorite style/perspective to do. Part map, part landscape painting.
Guild Master