Landscape changes have been observed throughout rural Europe over the past decades in relation to intensifying agriculture and land marginalisation. This is particularly true for Central and Eastern Europe as drastic political and socio-economic changes have taken place over the past century, as is the case for Latvia. Using a detailed time series of high-resolution remotely sensed images spanning from 1988 to 2007, the landscape structure (composition and configuration) in Vidzeme, central Latvia, is examined and compared between periods. Major recent events for the country, such as independence and entry into the European Union are covered. The effect on landscape structure of various socio-economic, infrastructure, physical variables, and national and European subsidies for agriculture is also investigated for the period 2000–2007. This analysis indicated that subsidies play a major role in maintaining agriculture, mostly by restoring the intensively used landscape developed during the Soviet era. The government is also shaping the landscape through its forest management. The 20-year span of the analysis underlines the non-linearity and reversibility of changes observed in the aftermath of independence.