The transition in Eastern Europe from command-driven to market-oriented economies brought about a sudden decline in agricultural production, which led to widespread farmland abandonment and subsequent reforestation across much of the region. We provide an overview of reforestation trends in post-socialist Eastern Europe. We also analyze remote sensing data and national statistics for three case studies (in Latvia, Romania, and Albania) to illustrate the diversity of drivers, spatial patterns, and possible future pathways of reforestation in post-socialist Eastern Europe. Results show an association between the level of economic development in a country and the extent of agricultural abandonment and subsequent reforestation, suggesting countries in the region may be at varying stages within the forest transition. In spite of the plethora of benefits offered by increased forest area, concerns exist in the region about threats of reforestation to the persistence of cultural landscapes and the biodiversity within them. It is recommended that the services of carbon sequestration, biodiversity maintenance, and cultural landscape preservation be incorporated more directly into the market economy.