Traffic surveillance and monitoring systems are the backbone of advanced traffic management and information systems. To date, these systems have focused on vehicular traffic. As a result, transportation systems have been advanced significantly for automobiles. However, less effort has been devoted to monitoring bicycle traffic in a more intelligent way, even though the bicycle is an important human-powered transport mode used to increase the sustainability of transportation systems due to its environmentally-friendly and emission-free characteristics. To increase the use of bicycles, it is fundamental to assess bicyclist’s perception of roadway environment, safety and comfort This study developed a novel methodology for evaluating bicycling environments based on the analysis of bicycle maneuvering data obtained from instrumented probe bicycles. In addition, how to integrate the proposed methodology in public bicycle-sharing systems is discussed to fully exploit the benefits of the proposed methodology in practice.