The aim of this paper is to question the supposed isolated and backward position of the region of Westerwolde, in the northeastern part of the Netherlands. Westerwolde’s geographically rather isolated condition has traditionally been brought forward to explain its backward image. Progressive peat growth ever since the Bronze Age occupation had transformed Westerwolde into an island. It was abandoned in the Late Iron Age, only to be recolonized in the early Middle Ages. During the 19th century, romantics were still admiring Westerwolde’s arcadian scenery and cultural traditions. In contrast, from the mid-19th century until well into the 20th century, protagonists of modern agriculture criticized its backward farming methods and standard of living, as well as its poor infrastructure. The central issues we address here is whether critics were justified in describing it as backward in the 19th century and whether concrete indications for this assumed backwardness are to be found in previous centuries. To jump from early medieval times to the 19th century is too big a leap, but combining archaeological and ecological data with a renewed and more critical study of written sources against the background of huge landscape transformations has brought a nuanced understanding of how Westerwolde evolved. We present new insights for the period starting with the conquest of Frisia and Saxony by the Carolingians and the introduction of Christianity, when missionaries and newly founded monasteries acquired agricultural assets and rights in the conquered region, up to the late Middle Ages. We therefore analyze church foundations, livelihoods or economic conditions of existence in connection with occupation structures, infrastructure and exchange of consumer goods interdisciplinarily. Conservatism appears easily confused with backwardness, and an aversion to innovation, with indifference, as underlying external factors often forced the inhabitants to adopt a wait-and-see attitude. Westerwolde is viewed continuously in connection ...