Depopulation has become a significant issue for local culture and built heritage conservation of many European rural areas. In San Giovanni Lipioni, a province of Chieti (Italy), this phenomenon has increased to the point that, nowadays, there are only 150 inhabitants and no significant economic activities. In this regard, the present paper aims to describe the crucial role of nature-oriented tourism in an economic, social, and revitalization strategy; how digital tools can be used to map and create a territorial trail system between municipalities; and, finally, outline the operations necessary for reactivation. The proposed methodology consists of a first digital survey phase using GPS receivers and outdoor navigation apps. The second phase would create a web platform with a system of virtual itineraries between villages, named “The Golden Leaves Paths”. After that, the last phase concerns the creation of analysis factsheets to guide the maintenance of paths and the design of iconic signage with artistic illustrations based on the oak leaves leitmotif to be installed along the paths. A local social promotion association will employ the outcomes, technical drawings, and strategies to reactivate paths as an attractive element for nature-oriented tourism and create a digital platform to foster the village’s territorial and cultural heritage.

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