<p>Climate Change proceeds faster than anticipated with disastrous events affecting large territories. Magnification of disastrous-prone areas redefines risk conceptions and perceptions, influencing planning decisions and community priorities at multiple levels. However, the spatial implications of Climate Change are still poorly understood, this underlying the need for new frameworks. A case study of Thessaly Region in Greece, recently affected by the devastating flood caused by Storm Daniel in 2023, is elaborated as a basis for formulating such a framework. Research method conducts a detailed examination of key periods that have significantly influenced spatial development and driven shifts in dominant socio-spatial paradigms. These is based on four key factors: (a) landscape transformations, (b) changes in population distribution across rural and urban areas, (c) demographic transitions, and (d) economic and political shifts. In Thessaly, a shift in paradigms is revealed, as the initial “retreat to nature” principle maintaining an organic and complex land use pattern within the floodplains was outplaced by a massive artificialization and homogenization of the landscape, to support the industrialization of agriculture; this accompanied by an unsustainable exploitation of natural resources. During the recent period this dominant paradigm is being challenged, with Storm Daniel coming after a decades’ long economic recession, and alongside rural population decline dramatically exaggerating uncertainty regarding Thessaly’s territorial future. Τhe failure of Thessaly’s anti-flooding infrastructure and conventional grey infrastructure planning emerges as the critical factor contributing to the region’s exposure and vulnerability. In the consequent section the new flood-control Masterplan delivered by a private company is critically assessed; where analysis shows that links to spatial planning perspectives are particularly missing.</p>