By developing digital models of specific heritage sites, we can reveal and better understand “Cultural Heritage Through Time” (CHT2). We have developed 4D models associated with different periods in time, dynamically navigable, for cultural heritage assets ranging from a building to an urban context or a landscape. By involving local citizens, who contributed to both the investigation process and the validation phase of this research, we have explored, in an iterative process, the contributions of a digital tool to the understanding of a site. We also saw how this active involvement worked as a catalyst, triggering further and longer-term participation, especially from local citizens, as they became more aware of the connection between the places they live in and their history. The 4D interactive models provide a link between past and present through digital representations of physical entities that are part of the everyday experience, generating in this way a process that enhances identification of local citizens with their cities.