Approaches to early medieval peasantry are often polarized, either enhancing the benefits brought by the weakening of aristocratic dominance or emphasizing the limited prospects for peasant development in the absence of a solid extra-regional trade network. This study offers a long-term overview of the peasant economy throughout the 1st millennium AD in the Upper Volturno Basin, between the town of Isernia and the monastery of San Vincenzo al Volturno. The reader is presented with data collected from two archaeological surveys, and is invited to scrutinize changes in settlement patterns, ancient land use and ceramic distributions while the main economic center shifted from town to monastery. These proxies of economic performance offer a vantage point to reconstruct the history of agrarian production and of exchange networks in Central Italy, opening a novel outlook on peasant social dynamics at a time when the Roman economic system transitioned into the feudal system. The results show that the “golden age of peasants” was an age of experimentation, forcing to reconsider the role of the peasantry in the making of the feudal economy.