Abstract: Autonomous structural health monitoring (SHM) of many structures and bridges became a topic of paramount importance for maintenance purposes and safety reasons. This paper proposes a set of machine learning (ML) tools to perform automatic feature selection and detection of anomalies in a bridge from vibrational data and compare different feature extraction schemes to increase the accuracy and reduce the amount of data collected. As a case study, the Z-24 bridge is considered because of the extensive database of accelerometric data in both standard and damaged conditions. The proposed framework starts from the first four fundamental frequencies extracted through operational modal analysis (OMA) and clustering, followed by time-domain filtering (tracking). The fundamental frequencies extracted are then fed to a dimensionality reduction block implemented through two different approaches: feature selection (intelligent multiplexer) that tries to estimate the most reliable frequencies based on the evaluation of some statistical features (i.e., entropy, variance, kurtosis), and feature extraction (auto-associative neural network (ANN)) that combine the fundamental frequencies to extract new damage sensitive features in a low dimensional feature space. Finally, one-class classification (OCC) algorithms perform anomaly detection, trained with standard condition points, and tested with normal and anomaly ones. In particular, principal component analysis (PCA), kernel principal component analysis (KPCA), and autoassociative neural network (ANN) are presented and their performance are compared. It is also shown that, by evaluating the correct features, the anomaly can be detected with accuracy and an F1 score greater than 95%.