This article discusses elite continuity and settlement pattern change in Zagori (NW Greece) from the late fourteenth to the nineteenth century. The peaceful assimilation of the regional and local elites into the Ottoman Empire (1430) led to adaptations in the montane landscape. Imperial and local archival research, ethnography, and landscape archaeology reveal that the Ottoman administration divided large decentralized settlements into smaller villages to accommodate local elites and new timariots. This topography of division (fifteenth to sixteenth centuries) gave way to a topography of adaptation (seventeenth to nineteenth centuries) when local elites influenced settlement patterns in forming the administrative unit the Zagorisian League.