The only time I ride on the sidewalk is when I'm pulling my daughter in the trailer. The streets around my house are just too narrow for me to risk having a car mis-judge the distance between their fender and the trailer when they pass. And, usually when I'm pulling her the top speed stays pretty low because the sidewalk is so freakin' bumpy, and there's usually a good amount of pedestrian traffic. I'm always worried about driveways though -- in fact the only time I've dumped the trailer onto it's side was trying to avoid a car rolling through a driveway. (My daughter, securely strapped in, looked at me with her eyes and mouth wide open -- I think she couldn't decide if she should laugh or cry. In the end she laughed).