The development of contemporary cities is characterized by increasing heterogeneity and dispersion of settlements, activities and services, and public spaces. Urban regeneration can play a key role in the revitalization of marginal or declining urban areas, enhancing the cultural patrimony as a structural component and promoting identity, social inclusion and the local economy. A particular case in point is the nineteenth- and twentieth-century military fortifications of Rome’s Campo Trincerato, a system of fifteen forts and three batteries of great historical and documentary value. The forts, today mostly in the process of being decommissioned, can represent, if viewed from a network perspective, an opportunity to configure an offer of spaces for culture capable of activating a process of regeneration of physical and immaterial relations, promoting shared paths of valorization and re-functionalization. Reasoning about the regeneration of this system means not only refunctionalizing structures, but also recomposing contextual, environmental, urban, social, and cultural relationships to restore urban quality and redefine the landscape of the contemporary city’s suburbs.