In the context of improving resilience in transport infrastructure, an emerging approach of indirect structural health monitoring is gaining attention, known as drive-by monitoring, instrumenting a vehicle with sensors to evaluate the bridges it crosses. However, their effectiveness has predominantly been investigated in ideal scenarios, with actual real-world applications being quite scarce. The research presented in this paper explores the feasibility of combining two routes: (1) fleet emissions reduction and (2) transport resilience enhancement, through drive-by monitoring integrated with shared mobility, including electric mobility scooter and bicycle. The information from drive-by data collected from shared mobility can give valuable information on critical transport infrastructure (e.g., bridges) and such a drive-by database has the potential for network level infrastructure condition assessment. In this paper, two different drive-by roadmaps are investigated subject to the flexibility of the bridges, namely partially or fully drive-by monitoring. To validate the proposed roadmaps, a full-scale pedestrian bridge was chosen for drive-by testing, where smartphone sensors and specialised accelerometers are mounted on shared mobility for data acquisition. Experimental results demonstrate that (i) smartphone sensing can provide data with similar accuracy compared to specialised accelerometers, (ii) bridge frequencies can be easily obtained from temporarily parked shared mobility, with a maximum relative error of 1.05%, (iii) both the bridge frequencies and operational deflection shapes are successfully extracted from the moving shared mobility by using variational mode decomposition and filtering techniques, and shared mobility’s GPS data along with moving speeds are collected for potential vehicle positioning and drive-by database updating.