One of the many urban planning strategies implemented in the U.S. is to invest in low-impact travel like bicycling. Because roads have largely been designed for cars, a primary concern for bicycling is in understanding how improving road environments can encourage bicycling. The three-part research study focuses specifically on the relationship between the road environment and bicycling behaviors. The first part examines bicyclist’s acute psychological stress in different road environments through a crossover field experiment. The second part examines the relationship between road environments and bicyclist routes through observational case studies in Davis and San Francisco, California. The third part examines student’s travel mode to school at three northern California high schools. The combined results from these studies and review of the literature demonstrate that large scale changes to road environments may be needed to influence bicycling perceptions, attitudes, and behavior.