European traditional cultural landscapes are increasingly modified by rural abandonment and urban growth processes. Acknowledged as of High Nature Value for providing multiple ecosystem services while contributing to human well-being, the future of these social-ecological systems is uncertain. Here we aim to (1) explore dominant land use and cover (LULC) changes linked to extensive livestock farming across an urban-rural gradient defined by a large city (Madrid) over the last three decades; (2) identify and classify the main driving forces shaping these landscape trajectories and; (3) acknowledge the main landscape values for promoting landscape stewardship under participatory governance frameworks. For doing so, we combine mapping analyses (CORINE Land cover) with stakeholder perceptions and positions. Our results show a dual process of progressive abandonment of agroecosystems linked to traditional livestock farming and an ever-increasing urban growth over the last three decades as the most important driving forces. The growing urban sprawl in areas close to Madrid begins to be perceived as problematic for interviewees. The decline of extensive livestock farming in detriment of tourism, particularly evident in rural areas far from Madrid, is perceived as a threat to the cultural heritage and traditions of rural people. This decline is also perceived as a worrying increase of wildfire risk. Stakeholders stressed the need of valuing extensive livestock farming to prevent rural-urban migration, dynamizing rural economies, conserving landscapes and traditions while producing food-quality products. Interviewees advocated for science-based, stakeholder-inclusive and participatory landscape planning and co-management, leading to more context-specific, regionalized policymaking.