Wow, this question was un-answered for a long time (4.7 years as of now)... In this year Wolfram Summer School 2021 (which I encourage you to apply for the next year), there was a project by Junyao Chen called "Draw a Character on the Street Map", which I think in essence is what OP is asking. Here is a stab at drawing spelling WOLFRAM on a street map:
Not bad, but if room for improvements is needed here are the full library of the functions and code used (you can download the notebook by scrolling to the bottom and clicking "Make Your Own Copy" button):
https://community.wolfram.com/groups/-/m/t/2314450
For fun demo, an interesting problem is a rotation of the shape on the streets grid, and here is the teaser of the result from the above post -- rotating letter "A":
