In this work, a self-powered wireless health monitoring system (SP-WHMS) combined with the Internet-of-Things (IoT) is proposed and implemented for a long-term and long-distance health monitoring of railway bridges. This system frees the wireless sensor nodes (WSNs) from their dependence on chemical batteries by using the piezoelectric energy harvester (PEH) to harvest the vibration energy from bridges to power the WSNs. The whole-process of the SP-WHMS including energy conversion, energy storage, energy management and application is analyzed at the first time through theory, simulation and experiment. For the energy conversion, a reported PEH model with high energy conversion efficiency (called D-M PEH) is refabricated, which can achieve a maximum average output power of 0.9 W under unit harmonic acceleration excitation. For the energy storage, a high-precision iteration analysis procedure (IAP) is proposed to predict the charging process of the strong-coupled PEHs and the charging process under non-harmonic excitations. The comparison results show that the IAP’s prediction deviates less than 3% from the experiment result and even less than 1% from the simulation result. For the energy management, an AP64500 chip with two adjustable input voltage thresholds and a stable output voltage ensures the normal operation of the SP-WHMS and makes the SP-WHMS suitable for different types of WSNs. For the application, the synergies between energy conversion, storage and management are considered, and the effectiveness of the SP-WHMS used on railway bridges is tested through an activation experiment. This work provides a technical guidance and framework for the implementation of the self-powered wireless monitoring on railway bridges.