Since the 16th century agricultural landscapes across the world have been restructured and aligned with modern modes of production and social organization. The introduction of new technologies, tenure regimes and modes of sociopolitical organization among other factors has fostered dramatic changes of landscape patterns in affected territories, leading to the creation of a new type of landscape. A distinctly modern agricultural landscape, characterized by rectilinear spatial forms, functionally segregated, specialized land use patterns, individualized decision making practices and an agricultural economy embedded within regional, globalizing networks of economic, technological and cultural exchange. In such landscapes, patterns of land use have since converged to an increasing extent, forming flows of correlated practices and associated ecological impairments observable across extensive arrays of otherwise discrete landscape contexts. This raises a number of questions for landscape ecology, including how to engage analytically with landscape change trajectories in a situation where decision making is resolved at an interface between local agency and deeply entrenched institutions and infrastructures of a capitalist modern origin. In this context, the purpose of this keynote address is to explore how the relationship between institutional and physical legacies of land use modernization affects decision making in contemporary agricultural landscapes. On the basis of a selection of European and postcolonial examples, it is discussed how alternative landscape futures formulated and aimed for by local decision makers are aligned with established conditions for landscape management, and how this can be conceptualized within a landscape ecological perspective.