How do we identify ancient fields and farming systems in areas where the same spaces of cultivation have been used repeatedly over thousands of years? In the limestone karst landscapes of northern Dalmatia, on the Adriatic coast of Croatia, drystone field walls, terraces, and cairns are common features that attest to generations of working the land for agriculture. While confounding archaeological objects due to complex histories of reuse, drystone terraced field systems throughout the Mediterranean are believed to have roots in ancient and prehistoric land use. Against this backdrop, this paper works to better understand the dynamic patterns and outcomes of field “recycling” through multiple lines of evidence for long-term changes in cropping patterns and agroecology in multi-millennial agricultural landscapes of northern Dalmatia. We compare archaeobotanical data from the Ravni Kotari plain to documents of preindustrial land use from the 1826 Franciscan cadastre. We also draw upon contemporary observations of traditionally managed, semi-wild olive groves on the nearby Adriatic island of Ugljan to better understand the land-use legacies inherent in the landscapes of northern Dalmatia today. These data show that, despite a relatively static agricultural built environment of field walls and terraces, Dalmatian communities held historically dynamic relationships with domesticated and wild plant ecologies. Prehistoric integration of cereal agriculture with wild forest resources appears to have shifted to commercial-scale domesticated arboriculture in the Classical period, leaving a multifaceted legacy of commercial agriculture, traditional farming, and rewilding among the contemporary cultural landscapes of Dalmatia.