Four thousand years of shaping the landscape, developing sustainable agricultural practices and products, and forming a symbiotic relationship with ecological systems in the Aposelemis Valley of Crete has been disrupted due to the building of a large dam in the heart of that landscape. The politics and decision-making that resulted in the building and implementation of this dam are already documented and analyzed in a recent paper (Chifos, et al, 2019). This paper re-examines what happened in this Valley from the perspective of the cultural/heritage advocates and where the barriers to protecting and maintaining this landscape were and still are. This thriving rural landscape with five inhabited old villages, was recognized as a Natura site, a Ramsar site, was experiencing new archeological finds from Minoan, Roman, and Venetian eras, as well as being championed by local cultural associations, an agricultural cooperative, active farmers and shepherds, and environmentalists. Every such place cannot become a designated cultural landscape through UNESCO, IUCN or other international or national programs. It is not clear that such designations would have stopped the momentum of this water resource management outcome. How can active living traditional rural landscapes survive conflicts with the demands of hyper-tourism, urban growth, EU policies, and centralized governance? This analysis of the Crete case provides an opportunity to identify the weaknesses and world views that left this rural landscape vulnerable to such destruction. Local and regional strategies, as well as the role of local decision-making, that could have prevented or lessened this destruction are discussed, contributing to the ongoing search for how to empower active living rural cultural landscapes to co-exist in a world of rapid change.