Driving safety, riding quality and fuel efficiency are heavily influenced by the surface conditions and structural integrity of roads, and the World Bank has identified it as one of the main factors in the analysis of road quality vs. user cost. This paper presents a proof-of-concept study on monitoring road conditions by analyzing the data in smartphones placed inside the backpacks of cyclists. We demonstrate by experimentation and data analysis techniques that it is feasible to obtain valuable information on the condition of roads from smartphones placed inside the backpacks of cyclists, including the assignment of acceleration signatures to specific irregularities and anomalies on the surface of roads, such as bumps and manholes. Moreover, this preliminary investigation shows the tremendous potential portable, mobile sensing platforms have in many future long-term applications such as the internet-of-things, urban mobility, digital twins and smart cities.