The town of Montemassi is situated in the municipality of Roccastrada, and its highest part contains the ancient castle that belonged, from the 11th century onwards, to the powerful Aldobrandeschi family, who turned the place into a centre of vital importance on the salt routes.
During the 13th century and the conflicts between the Guelfs and the Ghibellines, Montemassi, being a significant Guelf stronghold in the Maremma, was besieged and totally destroyed by the Sienese army. Rebuilt after the victory of the Guelf forces, it passed into the hands of Nello Inghirami Pannochieschi before suffering another fearsome siege from the Sienese in 1328.
This important military success, led by Guidoriccio da Fogliano, is depicted in the famed fresco by Simone Martini in the Palazzo Pubblico in Siena. Here it is possible to recognise the structure of the castle that today, despite a few collapses and the centuries of abandonment, stands almost unchanged.
On one side of the large, walled courtyard we find the old government palace, with its original doors and windows still intact; on the south side, we find the whole structure's best-preserved ruins, including a rectangular tower which, at ground level, contains of two large rooms topped by a cross vault.
Not far away are the ruins of an old rectangular church, in which you can still see two tombs belonging to local people with high status built into the stonework.
Even the surrounding town, typical of the area, was once defended by walls. Only a gate remains visible today, guarding the interesting Church of Sant'Andrea Apostolo.