It is a commonplace assumption that the medieval cities were ‘ruralized’ by the presence of vegetable patches, fields, and livestock. Historians and archaeologists have often taken evidence for agricultural cultivation in urban spaces as indicators of the breakdown of medieval urban fabric and economies, but urban gardens were not simply by-products of decline or devolution. They were created because people living in the city wanted fresh fruits and vegetables and dedicated space to grow them. The evidence from Italy makes clear that residential properties with access to cultivated spaces were controlled by urban elites, both private and ecclesiastical. The study of these urban vineyards, vegetable patches, and fields, through their textual and archaeological records, provides us a small window on to shifting social structures within medieval cities, the rises and falls in small-scale markets, and emerging ideals of charity. The combination of property documents with letters, narrative chronicles, and a considerable amount of recent urban archaeology make it possible to observe urban food provisioning in early medieval Italy and to relate the phenomenon of urban gardening with shifting power structures in the city.