This study investigates the continuity, change and discontinuity of human settlements in the northern Stig Plain along the Danube River in Serbia, with the aim to explore how the natural environment, human–land interactions, and historical events shaped the establishment, duration, decline, and reconstruction of these settlements. Particular attention is given to the Roman city of Viminacium, now largely covered by fertile farmland. The research combines theoretical perspectives on landscape and human–land relations with a review of sources on Roman urban development, case studies of settlement formation, development, abandonment and transition, and an analysis of Viminacium’s environmental and historical context. It examines why Viminacium remained the landscape’s only major urban centre, with no subsequent settlement built directly above it. Findings show that the natural environment strongly influenced settlement patterns, providing both subsistence and strategic advantages. The plain’s urban potential was fully realised only in the Roman period, through the establishment of a legionary fortress, technological advances, organised labour, and military order that overcame environmental constraints. Viminacium’s heritage integrates remains from multiple historical periods into a unique, evolving cultural landscape that warrants preservation, though its management remains challenging.