Fighting land degradation of semi-arid and climate-sensitive grasslands are among the most urgent tasks of current eco-political agenda. Particularly, northern China and Mongolia are prone to climate-induced surface transformations, which were reinforced by the heavily increased numbers of livestock during the 20th century. Extensive overgrazing and resource exploitation amplified regional climate change effects and triggered intensified land degradation that forced policy-driven interventions to prevent desertification. In the past, however, the regions have been subject to continuous shifts in environmental and socio-cultural and political conditions, which makes it particularly difficult to distinguish into regional anthropogenic impact and global climate change effects. This article presents analyses of historical written sources, palaeoenvironmental data, and Normalized Difference Vegetation Index (NDVI) temporal series from the Moderate Resolution Imaging Spectroradiometer (MODIS) to compare landcover change during the Little Ice Age (LIA) and current spectral greening trends over the period 2001–2020. Results show that decreasing precipitation and temperature records triggered increased land degradation during the late 17th century in the transition zone from northern China and Inner Mongolia Autonomous Region to Mongolia. From current climate change perspectives, modern vegetation shows enhanced physical vegetation response related to an increase in precipitation (Ptotal) and temperature (T). Vegetation response is strongly related to Ptotal and T and an increase in physical plant condition indicates local to regional grassland recovery compared to the past 20-year average.