While displaying diversified economic values, agro-ecosystems remain a relevant component of rural landscapes in Southern Europe. Coupled with the expansion of ecologically fragile areas because of climate warming, intensification and simplification of rural landscapes—e.g., in lowland—represent frequent trajectories of rural land-use change (RLUC) in the Mediterranean region and demonstrated to harm ecosystem functionality and ecological quality, especially in a context of socioeconomic transformations of landscapes. Additionally, an incipient ‘extensivation’ of geographically remote and economically marginal agricultural systems was also observed, likely following depopulation and land abandonment. The present study elaborated in this direction, providing an integrated RLUC evaluation scheme based on a multivariate analysis of land-use indicators derived from official statistics. This approach was applied to a continuous, long-term RLUC monitoring of a rural landscape in an ecologically complex Mediterranean region (Latium, Central Italy) experiencing multiple trends (e.g., lowland urbanization, crop intensification in gently sloping areas, and land abandonment/depopulation in steep zones) with diversified environmental implications. Based on administrative inventories, such evaluation was carried out over fifty years (1970–2020) in the study area, considering trends over time in selected crop surfaces at the municipal scale as inputs of a multiway factor analysis (MFA). This analysis quantifies stability in the main rural land-use types and possible changes in the dominant farming systems. Simplified indicators of land configuration (namely a crop intensity index and a rural woodland index reflecting ‘intensification’ or ‘extensivation’ of local farming systems) made available at the same spatial and temporal scales completed the informative picture corroborating MFA results. Taken together, our findings delineate multiple changes in rural landscapes, discriminating land-use trajectories in coastal and inland districts. These development trajectories were basically dependent on processes of (i) land abandonment in relict and remote areas, (ii) crop intensification in dynamic rural districts, and (iii) fringe urbanization along the coastal strip.