Monticchiello, already in Etruscan and Roman times, was a meeting point for the roads that connected the centers and communities of the area. It still retains the austere characteristics of medieval fortresses, sharply contrasting the Renaissance image offered by Pienza. The sturdy city walls and the tower of the cassero that stands on the hill are signs of the intense past of the village, a stronghold of the defensive system of the Republic of Siena. It is precisely with the passage under the protection of Siena that the history of Monticchiello begins, of which there is actually evidence dating back much earlier than the communal era, as shown by the fact that its name is said to derive from the Roman gens Clelia. From the 1200s, the village took on its current form with the walls, the cassero, and the church, and typical municipal institutions were established, all provided for and regulated by statutes in the vernacular language. It was then with the fall of the Sienese Republic in 1559 that Monticchiello fell under the Medici and gradually lost the role and importance it had had. In 1777, it became part of the municipal jurisdiction of Pienza. The propositurale church of Saints Leonardo and Cristoforo still stands today as a testimony to the period of maximum splendor of the medieval fortress, preserving numerous frescoes from the Sienese school dating back to the 14th and 15th centuries. Finally, Monticchiello and its inhabitants are characterized by a rare example of cultural autonomy and collective commitment: the "Teatro Povero" (Poor Theater). It was born and developed in Monticchiello long before its precise start date (1967). The theatrical experience is closely linked to the life and history of the community since the past. The performances offer a glimpse into bourgeois life, delving into current themes inspired by local history and evoking the now obsolete forms of peasant civilization. It is a kind of theater-life written by the characters themselves, that is, by the people of Monticchiello who, by acting themselves, testify to their own reality, presenting themselves with their authentic existential and social situations. Collateral events such as exhibitions and conferences accompany the theatrical activity throughout the year, reaching its peak during the summer period (from mid-July to mid-August, shows every evening except Mondays).