This chapter addresses unsupervised damage detection in railway bridges by presenting a novel AI-based SHM strategy using traffic-induced dynamic responses. To achieve this goal a hybrid combination of wavelets, PCA and cluster analysis is implemented. Damage-sensitive features from train-induced dynamic responses are extracted and allow taking advantage not only of the repeatability of the loading, but also, of its large magnitude, thus enhancing sensitivity to small-magnitude structural changes. The effectiveness of the proposed methodology is validated in a long-span bowstring-arch railway bridge with a permanent structural monitoring system installed. A digital twin of the bridge was used, along with experimental values of temperature, noise, trains loadings and speeds, to realistically simulate baseline and damage scenarios. The methodology proved highly sensitive in detecting early damage, even in case of small stiffness reductions that do not impair structural safety, as well as highly robust to false detections. The ability to identify early damage, imperceptible in the original signals, while avoiding observable changes induced by environmental and operational variations, is achieved by carefully defining the modelling and fusion sequence of the information. A damage detection strategy capable of characterizing multi-sensor data while being sensitive to identify local changes, is proposed as a tool for real-time structural assessment of bridges without interfering with the normal service condition.