Mining exploitation between Romagna and Marche has been very limited since ancient times due to the scarce metal resources that have determined their importation since Antiquity both in the form of objects and raw material in order to be worked and marketed. Traces of this marketing of raw materials, as far as the early Middle Ages are concerned, have been found in the port area of Classe inside warehouses built between the 5th and the 6th centuries. Over time, changes in the landscape of Romagna and the Marche have seen the birth of new settlements, for instance castles especially in the Apennine heights on the edges of the valleys that cross the landscape from west towards the Adriatic coast. The census of these new settlements that from the end of the 9th century began to characterize the Apennine heights then determines the exploitation of stone material from the end of the 11th century of the material associated with their transformation into stone castles, with extraction quarries directly below the surfaces on which the settlements were built. In most of these sites there are traces of production activities for iron objects, with metal probably imported from Tuscany. The only area where iron extraction has been hypothesized is that associated with the Pietra Rubbia castle, but despite the characteristics allowing the discovery of small metal veins, their presence is so scarce that its exploitation seems unlikely and uneconomical. The origin of the metals found in the various ateliers of the castle has not yet been established. Starting from the 14th century, in Valdinoce, between Romagna and Tuscany, the opening of sulphur quarries is also reported, perhaps linked to the production of gunpowder, which then increased towards the end of the Middle Ages and in the early modern age. The exploitation of gypsum from the quarries of northern Romagna is also significant, in various forms and with wide distribution since ancient times. The quarries of this precious material are used by fortified villages in a large territory that extends from the heights of the metropolitan area of Bologna, up to the territory of Rimini, with imposing castles that control their exploitation until the end of the 16th century. In this paper we present an overall picture of the investigations conducted by our research groups to show the transformations of this vast Adriatic landscape since all over the Middle Ages.