I recently downloaded some free software from ESRI called ARC GIS Explorer. I was working with it this weekend to see what it could do. Attached is a copy of a map I designed today, recreating a map that appeared in the August 2005 issues of Trains Magazine.
This program allows you to design thematic maps (background information including shaded relief and administrative boundaries) as well as add layers (green for the POTB Railroad). Final editing was done in PowerPoint which included text and symbols (city dots and highway markers). Fancier editing could be done in Adobe Illustrator; however, I was amazed how much I could do in PowerPoint. I just downloaded a free version of Inkscape, as that may be able to do some of the advanced editing techniques found in Adobe. Let me know your thoughts, comments or suggestions.