Roccastrada is one of the widest Italian communes (28.000 hectares). Situated on the ridge of an intensively cultivated plateau, Roccastrada maintains the aspect of a medieval town, distinguished by the beautiful 13 Church of Saint Nicola in the old part of the town. The Town Hall, the Municipal Library and the Theatre of the Concordi are located in the 19 C new part of the town.
Roccastrada, chief village of the district, was built around the 10th century, its main church, Chiesa di San Niccolò, was established around 1283. It keeps two frescos dating back to the sixteenth century: one representing the Annunciation, the other a Madonna with Child.

History

Montemassi is a medieval village, dominated by an imposing fortification, Montemassi Castle. The castle of Montemasi is, without any doubt, the most famous monument in the territory of Roccastrada, for its importance of historical document (it was represented on the famous fresco situated in the public palace of Siena attributed to Simone Martini) and for the high example of Gothic style architecture that it represents. The castle was repeatedly besieged during the fourteenth and fifteenth centuries and finally conquered in 1328 by the Sienese Republic.
This conquest is celebrated in a very famous and discussed fresco attributed to Simone Martini, in which we can see Guidoriccio da Fogliano, a mercenary soldier, hired by Siena that proudly enters a defeated Montemassi on the back of his horse. We can admire this fresco at the Palazzo Pubblico in Siena, inside the "Mappamondo Hall".
The historical center of Montemassi is very picturesque and still maintains today the aspect of a compact medieval hamlet at pine-cone form, there are no more traces of the city walls, at exception of a gate, that once were connected with the castle.

Roccatederighi is one of the most interesting and well preserved medieval village of this area, it is mimetically built on huge trachyte rock spurs called "i massi" overlooking the Maremma. We can still notice the remains of its "Cassero"(1) near the Tower Clock, and parts of the ancient walls. At the very top of the village there is a church, Chiesa di San Martino Vescovo, built around the tenth century. Both the village of Sassofortino, where we can notice several doorways carved in the local stone, and Roccateterighi are situated at the foot of Sassoforte, a 787 metres high mount where the remains of a mighty fortress lie: il Castello di Sassoforte.

Ribolla has been an important mining centre: lignite was excavated until 1954, when an enormous explosion stopped the coal extraction. The today’s village structure is developed on the basis of the existing mining village.

Sticciano stands on a small hill at the centre of the area of Monte Leoni. It is a natural terrace on the plain with extraordinary views. It is like being on a balcony which overlooks the Maremma, the sea and the islands of Giglio, Elba and Corsica. It can be reached only through a road, which is like a route of slow discovery, of increasing wonder. The old town is a meaningful scarcely inhabited medieval town. The very centre of the village is only accessible on foot, with acute corners and narrow passageways. The romanesque church, Chiesa della Santissima Concezione, also known as the church of Santa Musticola, is worth a visit. The church of Santa Musticola is made up of a single nave ending in a semicircular apse, with an elevated presbytery and a rectangular bell tower on the right, inside the church, and two interesting portals: the main one with an architrave decorated by two romanic crosses and the lateral one with a decoration made up of mouldings on the jambs and palm trees with crossed leaves on the frame of the double archivolt.
From Sticciano it is possible to walk up as far as Monte Leoni (616 meters of altitude), even though the path is no marked. On the top of Monte Leoni, some kilometres far from the village, there is a circular stone hedge indicated as the remains of the walls belonging to a fortification, with features similar to the castle of Moscona."

Torniella and Piloni are small villages surrounded by chestnut wood trees, they both introduce the visitor the river Farma Valley, a protected area of incredible beauty and peculiarities. On the road to Monticiano, one can reach Torniella. The castle of the Ardengheschi, the vassals of the Aldobrandeschi, forms the stronghold of the town.
One of many sign-posted walking paths around Torniella arrives at the waterfalls on the Farma stream known as i Canaloni. After an extended walk you find a little waterfall with rocks and natural pool.

The Benedictine monastery of San Salvatore di Giugnano, dedicated to San Salvatore, which include only the remains of the crypt and the Cistercian building, is situated at Le Casecce.
The surroundings of Giugnano have been populated since the prehistoric time; the place is remembered in documents of 9th century and before the year 1076 it became the seat of a monastery. Of the abbey today are visible a big gothic building and a Romanesque crypt covered by cross vault sustained by four columns with figured capitals. The floridity of the religious centre has been linked also to the control that the monastery had on the water and mining resources, abundantly present in the valley (in particular the medieval mines of silver copper of Poggio Mozzeto). Already in 13th century, perhaps for the impulse given by the Cistercians of St Galgano, the monastery was surrounded by numerous manufactories which, making use of the waters of the torrent Bai, were used as mills and ironworks

The Farma Nature Reserve (it) situated between Monticiano and Roccastrada, includes the middle stretch of the very beautiful and wild valley where the stream Farma runs, the main tributary of the river Merse, and the upper course of Lanzo, a long stream flowing into the river Ombrone at Paganico.

Roccatederighi

Sticciano

I Canaloni

Trekking in and around Roccastrada | download pdf