In the Netherlands, most high and dry land was settled and cultivated as early as the prehistoric period. Many lowlands, on the other hand, remained essentially unreclaimed until well into the Middle Ages. Since then these areas, too, have witnessed rapid change, physically as well as socially. Usually in medieval reclamation areas, under frontier-like conditions, settlers managed to become free farmers. This paper discusses the interesting two-faced character of the social developments in some of the outlands along the margins of the civilised world. In some areas elite groups emerged or expanded, and castles and castle-like dwellings were shooting up far and wide, while wilderness areas were rapidly being transformed into highly productive arable land. Elsewhere smallholders and paupers settled, or were forced to settle involuntarily. In the latter cases the local economy was largely based on peat cutting and small-scale subsistence agriculture. Socially, outlands (reclamation areas) therefore took very different paths, which is still recognisable today. The history of these social contrasts is complex and deserves more research. Different opportunities as well as the ability and freedom to exploit them seem to have been key factors.