Understanding land system dynamics is fundamental for policy-making from local to global scale. Land system is a combination of land use, land management and territorial practices. To attain such complete information about landscape structures is a challenging task. Aiming to deepen knowledge on land systems, we applied a methodology meant to achieve a broader understanding of dynamics in the Sítio de Monfurado (SM), a Natura 2000 site and holder of High Nature Value farming systems. To do so, we combined spatial analysis of land system changes with a participatory approach designated as Territory Game. While the spatial analysis shows little change in the SM land systems, the territory is perceived as fast-changing by the territorial actors (e.g., stakeholders with an explicit role in territorial development). At both scales, and in agreement with literature, we find trends of simplification and intensification in land systems, typically associated with the reduction of multifunctionality. The combination of both approaches contributed to the understanding of past changes, the drivers that induce such changes, how these are interpreted and, how to act upon them in the future. The proposed combined methodology can bring new useful insights for policy-makers, although scaling from local to broader scale remains a challenge.