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The castle is undoubtedly the most famous monument in the municipality of Roccastrada, if not in the entire Upper Maremma, due to its historical significance (it is depicted in the famous fresco "Guidoriccio da Fogliano at the Siege of Montemassi" in Siena's Palazzo Pubblico, attributed to Simone Martini) and for its outstanding example of Gothic architecture. The fortification, which crowns a 280-meter hill above the town, consists of the remains of two main buildings: to the north is the Palazzo/Mastio, with the base of the sloping wall featuring numerous large windows, indicating its residential and not strictly military function, and the remains of a polygonal tower.

The perimeter walls are still partially visible, especially in the southern section, where an arched gate surmounted by three rounded stones stands. At the highest point of the hill stands the imposing stone keep, which extends around a courtyard. Within the walls is the church of Santa Maria Assunta, dating back to the 13th century but completely renovated in the late 19th century. It has a distinctive urban layout, dominated by an imposing stone keep arranged around a courtyard accessed through two round-arched gates, defended by a large tower with a massive base.

Massa Marittima is a fortified medieval village located on a hill, known for its beauty and wealth of artistic and architectural heritage. Key attractions include the magnificent Piazza Garibaldi, with the Cathedral of San Cerbone, the Palazzo del Podestà, and the Palazzo Comunale. Other points of interest include the Fonti dell'Abbondanza with its famous fresco of the Tree of Fertility and, in the upper town, the Torre del Candeliere and the Cassero Senese within the medieval walls.

Massa Marittima is a municipality located in the southern area of the Colline Metallifere, an area that has been inhabited since prehistoric times, as documented by numerous archaeological finds. The settlement is thought to be of Etruscan origin, but the city's most important period began in the 9th century, when it became a bishop's seat. From then until the 14th century, the city reached its peak splendor, thanks in part to the area's abundant mineral resources.

In 1335, Massa Marittima lost its political autonomy, having to yield to the conquest of Siena, which had long been attempting to seize control of the Massa Marittima mines. A period of economic and demographic decline followed, further exacerbated by the plague of 1348. Despite the serious problems, however, mining activity was never completely abandoned, although it was certainly significantly reduced. The Medici family, who incorporated the province of Siena into the Grand Duchy in 1557, attempted some interventions to promote the area's recovery, while a significant revival occurred in 1737 with the arrival of the House of Lorraine as successors to the extinct Medici family.

Every August 14th the Palio dei Ciuchi takes place, a very heartfelt folkloristic event where the five districts (Corso, Ventosa, Torre, Tramonto and Nobili) compete for a banner painted by local artists. During the same month, "Medioevo nel Borgo" is also organized, a suggestive medieval festival known throughout Tuscany with jugglers, musicians, acrobats and stalls with artisanal products, for a leap into the past.

Roccatederighi stands on a spur of Mount Sassoforte, from which you can enjoy a wide and splendid panorama of the Maremma. The town still retains its medieval charm intact, in addition to the suggestive arched entrance gate and some tower houses. But the peculiarity of this village is given by the close link it has with the rock on which it rests, trachyte, a volcanic rock that has been exploited to build houses and other buildings, dig alleys and squares, and of which boulders and outcrops can be seen in various parts of the center. you can also find the remains of the ancient fortress and some sections of the original walls, dating back to the fourteenth century. In the upper part stands the tower, rebuilt in 1910 with a large clock that marks the time of this corner of Tuscany.

This climb was supposedly named after a German cyclist who is no longer with us. All this was written by a friend of his on a yellow sign at the foot of the climb. The climb is steady all the way up to the "acqua bona" (good water), quite tough, and typically doesn't give you even 10 meters of respite. In 2018, the Kapannenberg time trial took place. Fifty-three athletes registered on September 29th, and it was organized by the Velo Club Massa Marittima, in collaboration with the UISP Cycling Association of Grosseto. The 5-kilometer time trial course started from the former miners' village of Capanne and ended near the Massa Marittima prison. The fastest time was set by Fabio Cini of Cicli Copparo with a time of 10:21.67. And how long have you been doing it?