Agricultural abandonment has given rise to novel landscape dynamics worldwide. This paper investigates abandonment and post-abandonment dynamics in continental Portugal as a hotspot of landscape change. We mapped the spatial patterns and drivers of recent (1995–2018) land use changes in a remote mountainous region as post-abandonment trajectories, based on detailed land use/land cover data made available by the Portuguese government. We showed that ‘Revegetation’ trajectories, indicative of agricultural abandonment, were still widespread between 1995 and 2007. However, between 2007 and 2018, the landscape was much more stable with ‘Return to agriculture’ as the dominant change trajectory. To understand what drives landscape changes after abandonment, we explored the influence of a wide range of potential biogeophysical and socio-economic drivers on the observed trajectories. We contrasted different landscape outcomes in binary logistic regression models with the potential underlying drivers as independent variables. The regressions revealed that the most significant determinants of these alternating dynamics are existing land use, climate, slope, protection regime and accessibility. The results of the regressions are at times counterintuitive and give important indications of the changing spatio-temporal scales at which these variables exert influence on the landscape outcomes. However, the regression models’ limited accuracies highlight the need for deeper investigation of the socio-economic and historic context of the observed changes. Improved understanding of the (drivers of) alternative dynamics following agricultural abandonment can help inform policy decisions regarding agriculture and cultural landscape preservation.