Due to economic and environmental issues, bicycles have been regaining their significance as a transportation vehicle in urban scenarios. To further drive this desirable trend, policy makers must have the tools to access current bicycle infrastructures and road safety concerns. Fundamental for this assessment is a deeper understanding of how cyclists use current infrastructures, if the cycling experience results in stressful events, and the conditions of the current infrastructure. We here introduce a new platform, SMARTcycling, that, by taking advantage of the mobile power available to a smartphone, captures and stores data from several sensors, namely an action camera, a cardio signal acquisition belt, and smartphone’s Global Positioning System (GPS) coordinates. The data is further processed and, through visual cues, we access the cyclist driving events and road condition cues. SMARTcycling also detects the cyclist stress using the electrocardiograms (ECG) from the belt. We further contribute by making available a dataset containing the sensors data from 10 paths over two cities in Portugal. On this dataset, we show our initial promising results on event detection, road condition identification and stress assessment.