This paper identifies the effect of passing distance laws on drivers’ perceptions and behaviors when passing bicycles. Using an instrumented bicycle, the study measured bicycle passing in a 25-h naturalistic field experiment using video recording and an ultrasonic distance-measuring device. In order to evaluate the effect of passing distance laws, the study examined jurisdictions with a three-foot passing law, a five-foot passing law, and no passing law. The experiment required a bicyclist to ride the instrumented bicycle in two-lane and three-lane roads to capture the distance between the bicycle and the overtaking motor vehicle. An Ordered Probit model was adopted to describe the relationship between a discrete dependent variable (i.e., passing distance) and independent variables. The results demonstrated that drivers’ overtaking distances were significantly greater in locations with the five-foot passing law than in other areas. The study also found that roads with paved shoulders, wider travel lanes, and a greater number of lanes contributed to greater passing distances. In contrast, we found that the passing distance was shorter on roads with shared lane markings (i.e., sharrows) or a higher share of heat vehicles. Moreover, a survey was conducted in locations with different passing laws and ordinances to determine drivers’ awareness and the effect of such policies on drivers’ behavior. The study illustrates that almost 70% of drivers in areas with a passing law were unaware of any existing laws requiring drivers to maintain a distance from bicyclists. These results can be useful to transportation engineers, policymakers, and legislators who intend to provide efficient designs for road infrastructure to better accommodate bicycles.