This paper offers a preliminary numerical analysis of the “Treponti” bridge in Comacchio (Ferrara, Italy), a distinctive landmark recognized for its unique design. The first section of the paper discusses the history of the bridge and provides context on the city and the region that influenced such a structure. Additionally, details about the construction are included. The paper then elaborates on the numerical analysis performed using the Finite Element (FE) software Abaqus, where the central vault of the bridge was modeled with a concrete damage plasticity (CDP) model. This analysis examines soil settlement at one of the piers of the bridge, a phenomenon observed through surveys. The results, quantified in terms of tensile damage, were compared with actual observed damage. The primary objective was to explore the failure mechanisms induced by soil settlement. Furthermore, although still in the early stages, this comparison also aimed to partially validate the numerical model.