When I lived in Santa Monica, California, I started a project to walk all of the streets of Santa Monica in alphabetical order. I made it up to the D's before my wife and I moved to Oak Park.
Oak Park is a bit smaller and while I had projected the Santa Monica project would take two years if I walked every week, I think I can do Oak Park in a year.
The rules: I'm walking the streets in alphabetical order, end-to-end. I try to do a bit of research before and after the walk to be able to find interesting things to write about and take lots of pictures to help provide some sense of the streets.