Ask people who know

Bikes are still the most efficient form of transportation yet invented, but still a major pain if you can't figure out a safe way to get from here to there.

You have two choices: You can spend months pouring over maps, driving test routes, observing traffic patterns, figuring out how to get around hills, and basically talking yourself out of it, OR, you can visit sites such as BIKELY, where people who regularly ride routes in your town tell you which way to go.

Another great resource would be an integration to Google Maps, since we're all using that now, anyway. The only problem? Google doesn't offer that yet! Peter has the right idea going!