Masonry bridges are common in many countries and their maintenance is a critical task, to preserve not only architectural heritage but also the embodied carbon invested in their construction. Sensing technologies can offer vital information to engineers responsible for these structures. In this paper, a multi-sensing approach is used to study the behaviour of a skewed, three-span masonry rail bridge in the UK, focusing on its deformation history and the movements at four transverse fractures that extend the full width of the bridge. Specific technologies include laser scan analysis, videogrammetry, and Fibre-Bragg gratings (FBGs) to monitor the multi-dimensional bridge response, which at the transverse cracks is of particular concern to engineers. Based on these data, the distributed nature of the structural behaviour of the bridge is discussed. The results demonstrate that complex masonry bridge degradation can be quantified and tracked, providing crucial insights for bridge maintenance and structural interpretation.