Roccatederighi stands on a spur of Monte Sassoforte in the municipality of Roccastrada, from which there is a wide and splendid panorama of the northern Maremma. Since the 10th century it has belonged to the Aldobrandeschi estate, while in the early 13th century it was ruled by the local lordship of the Tederigi or Tederigoli dei Guachi, from which the name of the town derives. Toward the end of the century it became part of the possessions of the Republic of Siena, following its fortunes until it became part of the Grand Duchy of Tuscany in the mid-16th century.
Although the military campaign of 1553 by the armies of the Marquis of Maragliano destroyed it almost completely, the village still retains its medieval charm intact, as well as the striking arched gateway at the entrance and some tower houses. But the uniqueness of this village lies in the close connection it has with the rock on which it rests, trachyte, a volcanic rock that has been exploited to build houses and other buildings, carve out alleys and squares, and of which boulders and outcrops can be seen in different parts of the center.
In the upper part are the characteristic "Massi" of rhyolite, which tower above the town and from which there is an extraordinary panorama that takes our eyes as far as the sea and the islands of the Tuscan Archipelago. In this part there are also the remains of the ancient fortress and some sections of the original walls, dating back to the 14th century. Next to it stands the tower, rebuilt in 1910 with a large clock that marks time in this corner of Tuscany.
Suspended on a spur of rock a little further down is the Church of San Martino Vescovo, which preserves a delightful painted tablet dating from the early 17th century depicting the infant Jesus and the Madonna with St. Augustine supporting the castle of Roccatederighi. Finally, in Piazza Garibaldi worthy of attention is the Church of San Sebastiano.
Every August 14, the Palio dei Ciuchi is run, a heartfelt folkloric event where Roccastrada's five contrade (Corso, Ventosa, Torre, Tramonto and Nobili) compete for a banner painted by local artists.
Also organized during the same month is "Medioevo nel Borgo", a charming medieval festival known throughout Tuscany with jugglers, musicians, acrobats and the stalls with handicrafts, for a blast from the past.