Landscape is a reflection of natural and socio-economic processes. When socio-economic situations change, this alters land use and leads to changed land use patterns. An extensive spatial study of rural landscapes in Hiiumaa Island in West Estonia, based on available aerial photos from 1956 to the present has highlighted significant changes. These include the simplification and polarisation of land use patterns, an overall decrease in agricultural land, especially that of natural and wooded grasslands, and also a gradual increase in forests. The greatest change in land use pattern took place by the beginning of 1980s, then the initial traditional and diverse landscape pattern had become much more simplified and polarised as a result of collectivisation, land reclamation and the wider use of industrial methods in agriculture. The remarkable changes in land ownership and agricultural land use intensity, since the end of the 1980s, have not yet caused any significant changes in developed landscape patterns. This paper examines transformations in the traditional high value farmlands of semi-natural grasslands and wooded meadows and pastures, and the impacts and possibilities of recent political and socio-economic reforms in the preservation of traditional landscapes and biodiversity in rural areas. These factors involve land re-privatisation since 1987, reclamation of independence in 1991 and accession to the EU in 2004.