The castle is one of the most important monuments in the Municipality of Roccastrada.
It was mentioned in documents for the first time in 1205. It was built on a hillock along what is now Via Cavour 101, which connects Massa Marittima (9km) with Abbadia San Salvatore (10km).
In a fresco by Simone Martini on display in the Palazzo Pubblico di Siena this monument is represented and made famous. It is a military fortification located on a hill at an altitude of 280 m. that also has housing remains.
Its appearance is very suggestive and recalls the Lord of the Rings’ scenery, Tolkien’s famous tale.
These are ruins, but you can recognize his buildings’ Gothic features: a palace, a polygonal tower, and a quadrangular tower.
Its particular conformation testifies to the presence of a castle, and its windows’ width denoted a not only military construction.
Probably there was a certain life of the court. However, it is not easy to define, between the various passages of ownership, at what period the civil and military works were carried out.
The troubled history of this place follows the historical events of the area. Around the year 1000, it was owned by the powerful Aldobrandeschi family, but in 1260 it was almost destroyed by a siege.
In 1306 the castle was submitted to the Counts Pannocchieschi first and to the Verdelli later, owners of many territories in the area.
Various attempts at rebellion in Siena turned the castle into the theatre of battles, always sedated in blood.
It is not difficult to imagine how, during the Middle Ages and the Renaissance, this stronghold was the stronghold of proud independence from Siena, the pre-e pre-e favored power of the area.
Thus from 1400, it was decided to dismantle the fortress to prevent further seditious pressures from spreading. Since then, the various passages of ownership concerned only the fiefdom and the land.
In recent history, the Municipality has purchased the property, and improvements have been made to ensure access to the castle’s remains.
So the whole village of Montemassi, located at the foot of the castle, has purchased a particular charm. The village has maintained the appearance of a “pine cone” village, and it is still possible to recognize the door that connected the village to the castle.