Upon the Hill of Monticchiello many Etruscan and Roman hints have been found. Already in the 8th century the community of Monticchiello submitted to the Amiata Abbey of Saint Salvatore. Then the Castle passed to Aldobrandeschis, to Forteguerris and then to the Church who gave it as a feud to Teutonic Knights, until the aegemony of Siena Commune prevailed even in Orcia Valley.
Under the Balzana Monticchiello became a borderline fortress. Charles the 5th succeeded in storming it in 1553 but the heroic resistance by the inhabitants remained famous for a long time. Until 1778 the small Commune administered by its own statutes. During the last World War on April the 6th of 1944 Monticchiello was the scenario of a dramatic battle by which the local resistance army prevailed.
For about 20 years in Monticchiello there has been the Teatro Povero (Poor Theatre) working by success of critics and public. It became one of the main cultural institutions of the area. In the second half of july the inhabitants show off a Self drama" created altogether in the wintertime and starting since the story of community faces the modern themes.
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