Google Maps directed us from the capitol city of New Hampshire to a small town in Maine via the most circuitous, serpentine, seemingly haphazard route imaginable. With some guessing about where the right turn stopped and the left turn started, and the roads with no name/route number posted, we made it to our destination.

For us it was fun and only a little stressful because we had promised to arrive at a certain time. Also, we were in a car driving through rural New England. My comment (and question for Google Maps experts) is that I think Google Maps algorithm looks for a route that approximates the straight line distance between points. It doesn't matter if some of those roads are unpaved, include a neighborhood cul-de-sac that happens to connect to through road, or lots of other weird routes that a human wouldn't suggest to you.