Step 1: Design
A word of warning here- I spent waaay too many hours getting this map right in photoshop. It's mostly my own fault for being a perfectionist, just be aware that it will take a lot of tweaking to get the results I did (you can download my eps file below).
Basically my process was to compile the screenshot from woodcutmaps with a few screen shots from google maps (for extra detail), and use the magic wand tool to extract three layers- water, street, and land from the images. I used the "refine edge" option of the magic wand to make sure I was generating smooth, high-contrast edges. I also ended up using the line and rectangle tools to draw in a fair amount of the streets by hand.
Eventually I ended up with three layers of color (fig 7). I exported each layer as a png and imported them in illustrator. I used the live trace function in illustrator to generate outlines of the shapes and export as eps (attached below).