The study has developed an online geospatial database for assessing the complexity of roadway heritage, overcoming the limitations of traditional heritage catalogues and databases: the itemization of heritage assets and the rigidity of the database structure. Reflecting the current openness in the field of heritage studies, the research proposes an interdisciplinary approach that reframes heritage databases, both conceptually and technologically. Territorial scale is key for heritage interpretation, the complex characteristics of each type of heritage, and social appropriation. The system is based on an open-source content-management system and framework called ProcessWire, allowing flexibility in the definition of data fields and serving as an internal working tool for research collaboration. Accessibility, flexibility, and ease of use do not preclude rigor: the database works in conjunction with a GIS (Geographic Information System) support system and is complemented by a bibliographical archive. A hierarchical multiscalar heritage characterization has been implemented in order to include the different territorial scales and to facilitate the creation of itineraries. Having attained the main goals of conceptual heritage coherence, accessibility, and rigor, the database should strive for broader capacity to integrate GIS information and stimulate public participation, a step toward controlled crowdsourcing and collaborative heritage characterization.