Already in Etruscan and Roman times, a meeting place for streets that connected centers and communities in the area, Monticchiello preserves the austere features of medieval fortresses. The sturdy walls and the tower of the keep that stands on the hill are the signs of the intense past of the village, the bastion of the defensive system of the Republic of Siena. Every summer (from mid-July to mid-August), there is the Teatro Povero, a rare example of cultural autonomy and collective commitment that characterizes the country and its inhabitants.

Founded in 1967, this theatrical experience is a component closely linked to the life and history of the community.

The shows are a cross-section of country life that offers an in-depth analysis of current problems drawing inspiration from local history and re-proposing the forms of rural civilization. It is a sort of theater-life written by the same characters, that is by the people of Monticchiello who, reciting herself, she witnesses her own reality by presenting herself with her authentic existential and social situations