Raster (bought) [e.g. Photoshop, PaintShopPro, Painter]
Raster (free) [e.g. GIMP]
Vector (bought) [e.g. Illustrator, Corel Draw, Xara]
Vector (free) [e.g. Inkscape]
Vector (Symbol driven) [e.g. CC, Dunjinni]
Online Generator [e.g. City Map Generator, Fractal World Generator]
Fractal Generator [e.g. Fractal Terrains]
3d modelling [e.g. Bryce, Vue Infinite, Blender]
Scanned hand drawn maps
Drawing Tablet and pen [e.g. Wacom]
I've been using Seashore, sort of a stripped down GIMP for MacOS. It's quite a bit simpler than a full version of GIMP but not well-supported anymore. It's the tool I've been using to teach myself the very basics and crank out a handful of simple maps for gaming.
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