Afforestation trends were compared between two continentally-distinct, yet similar ecoregions to characterize similarities or differences in forest advancement due to natural and anthropogenic forcings. Temporal changes in forest cover were analyzed using high resolution aerial and satellite photographs for Southeast Iowa, USA, and satellite photographs for the western Belgorod Oblast, Russia. An increase in forested area was shown to occur over a 44-year period from 1970-2014 in Iowa where afforestation was reflected by the aggregation of smaller forest units. In the Belgorod region the opposite occurred in that there was an increase in the number of smaller forested units. The rate of forest expansion into open grassland areas, previously used as haying lands and pastures, was 14 m decade −1 and 8 m decade −1 in Iowa and the Belgorod Oblast, respectively. Based on current trends, predicted times for complete forest coverage in the study areas was estimated to be 80 years in Iowa and 300 years in the Belgorod Oblast. In both the Iowa and Belgorod Oblast, there was an increase in annual precipitation at the end of the 20th and the beginning of the 21st centuries, thus providing a contributing mechanism to forest advancement in the study regions and implications for future management practices.