This paper engages with a specific feature of former military landscapes, the Cold War barracks, located in a specific territory, the Friuli-Venezia Giulia region in north-eastern Italy, at the former border between the Western and Eastern blocs. Based on several academic activities, such as an international workshop and didactical experiences, this work focuses on the Trieste Barracks in Casarsa della Delizia (in the province of Pordenone) as a laboratory for new landscape solutions to reintegrate a derelict military site into civil society. The main outputs of the research are: 1) updating the international scientific literature and the relative research gaps in the discourse of Cold War post-military landscapes; and 2) an innovative landscape-oriented approach to a former military landscape founded on locally based long-term solutions in terms of resilience and sustainable development. Our research aims to demonstrate that Cold War landscapes have primarily been neglected in the academic field, but academic work in collaboration with local actors can result in feasible solutions to export to other cases.