The current methods that aim at monitoring the structural health status (SHS) of road pavements allow detecting surface defects and failures. This notwithstanding, there is a lack of methods and systems that are able to identify concealed cracks (particularly, bottom-up cracks) and monitor their growth over time. For this reason, the objective of this study is to set up a supervised machine learning (ML)-based method for the identification and classification of the SHS of a differently cracked road pavement based on its vibro-acoustic signature. The method aims at collecting these signatures (using acoustic-sensors, located at the roadside) and classifying the pavement’s SHS through ML models. Different ML classifiers (i.e., multilayer perceptron, MLP, convolutional neural network, CNN, random forest classifier, RFC, and support vector classifier, SVC) were used and compared. Results show the possibility of associating with great accuracy (i.e., MLP = 91.8%, CNN = 95.6%, RFC = 91.0%, and SVC = 99.1%) a specific vibro-acoustic signature to a differently cracked road pavement. These results are encouraging and represent the bases for the application of the proposed method in real contexts, such as monitoring roads and bridges using wireless sensor networks, which is the target of future studies.