 Numerous traces of Etruscan and Roman civilizations have been found on the hill where Monticchiello is located. In the eighth century, the town was run by the San Salvatore abbey near Monte Amiata. The castle was later controlled by the Aldobrandeschi family, followed by the Forteguerri family, and then by the Church. After a feud, the Church handed it over to
 the Cavalieri Teutonici, until the municipal government of Siena finally prevailed across the Val d'Orcia. For about twenty years now, the critically and publicly acclaimed "Teatro Povero" has operated in Monticchiello and has become one of the leading cultural institutions in the area. During the second half of July, the town residents put on a "self-drama", which they compose over the winter and which addresses current events, starting with the story of their own community.
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