The small island of Walcheren in the estuary of the river Scheldt is home to a number of important early medi eval settlements. Building on the results of new fieldwork, this paper discusses their urban character and challenges the conventional narrative of disjointed stages rooted in settlement typo logy. It proposes a contextualized biographical approach in order to reconstruct a more encompassing view of urban continuities and discontinuities. In doing so, it highlights the long persistence of urbanism on the island, across conjunctural shifts and low points, and relates the observed patterns of change to developments locally and more broadly, in the Low Countries and beyond.