The territory of the present hamlet of Casole d'Elsa, Tuscany, has been an important place since the primordial times not only for the exploitation of natural resources, but also for the location along important communication routes between the various areas of the Tuscany center -west and inward penetration. It rises on the first propaganda of the Metallifere Hills, lapped by the rivers Cecina and Elsa and framed by the massif of Montagnola Senese.
The first secure traces of human resources date back to the Neolithic age. If the age of the Bronze Age, characterized by the beginning of exploitation of the mineral resources (copper) in the area of the Metallifers Hills, is poorly attested, the Iron Age (IX-VIII century BC) assumes more defined characters. With orientalisation (VII century BC) and above all with the archaic age (VI century BC), we witness the emergence of small local potentates living on farms spread across the territory and gaining wealth from the ferocity of the soil and the control of the communication paths. With the Hellenistic age (the second half of the IVth-beginning of the 1st century BC), the hegemonic role of Volterra is increasingly evident. Casole is attested by the first decades of the XI century as an important castle. Early references to the establishment of two consuls of Casole date back to 1208, while, a few years later, castellanza pacts again linked the Colle and Casole communities, the latter represented by the figures of two rectores societatum. Despite the articulated imperial privilege of Frederick II of Swabia (1224), which recognized and legitimized the interference of the volcano bishops with regard to the nomination of the rector or consuls of Casole, as well as of other Valdelene towns, in the middle of the century now completely structured, with a podestà, a council, a college of "elders" and, presumably, already with its own statutory elaboration.
Over the course of the 13th century, Siena's interference increased steadily, under whose domain Casole passed after the victory of Montaperti (1260). The village was home to the ancient church of Santa Maria Assunta, whose first certificates date back to the XI century. The primitive church, enlarged and reconstituted in solemn forms in 1161, would have known a substantial alteration of the structure and a further rise and expansion between the end of the 13th century and the early 14th century. The church and its cloister were the seat chosen for the conclusion of acts of salient importance for Valdelian history. During the last twenty-two years of the 13th century some important figures were distinguished in Casole, socially and patrimonially attributable to rulers holding majestic domination forms, leading members of the ecclesiastical aristocracy, interpreters of excellence in an elite juridical culture derived from studies of canonical and civil law, frequentors of various degrees of the papal court, but always with roles of absolute importance.
In 1313, on the occasion of the descent into Italy of the army of Arrigo VII of Luxembourg and the concomitant rebirth of the powers of power and autonomy that peculiarly characterized the aristocratic components of philosophical and neo-ghibelline faith in the Tuscan municipalities, Casole rebelled Sienese government and received an important imperial garrison on the initiative of the dominion Ranieri, son of Porrina, supported by the Ghibelline faction of the castle, to which the Andrei also belonged. The following year however, following the substantial failure of Henry VII's intervention in Italy, he found the subordination of Casole to Siena fully reconfirmed, as evidenced by a large and articulated stipulation between the two communes (April 1314). Ranieri del Porrina, banned with his son, was exiled to Pisa, the stronghold of Ghibellinism in Tuscany. From the 16th century the events of Casole follow those of the Grand Duchy of Tuscany and therefore of the new Italian State.
The writer Carlo Cassola set up his novel The Girl of Bube in the hamlet of Monteguidi.