Concerns for the environment and personal health have made bicycling an increasingly popular mode of transportation in the US. Understanding how bicyclists move through the built environment is critical to designing infrastructure that promotes safe riding. Tucson is a prime location to study cyclist behavior because of the large cycling community, good weather, and significant investments made in cycling infrastructure. This study uses Tucson as a case to ask: 1.) How do these different types of riders interact with the built environment? 2.) Where are the problem areas with motorists for different types of riders? Moreover, 3.) How can this study be designed to be useful to the city transportation planning department to improve on the 5 E’s, Engineering; Education; Encouragement; Enforcement; and Evaluation & Planning, of bicycle planning? These questions will be answered through analysis of GPS files, video recordings from rides, Strava data, observations, surveys, and interviews with stakeholders. The outcomes of the study will address the gap in understanding how cyclists interact with the built environment while promoting collaboration with the City of Tucson and advocating for infrastructure improvements. Funds will be used to purchase the GPS devices, video devices, a limited Strava dataset, and possibly for a student research assistant to review and code video footage.