Montemassi: a pretty medieval village

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Montemassi is a charming medieval village in the Grosseto Maremma, located in the municipality of Roccastrada along the road that connects Roccastrada to Massa Marittima and Gavorrano, about 15 km from the Giuncarico exit of the Aurelia. The village is located on the slopes of a hill full of olive trees, at an altitude of 280 metres.


The village was founded in the Middle Ages by the Aldobrandeschis, the oldest document attesting to its existence dates back to the 11th century. Siena conquered it for the first time in 1260, subsequently the castle became a fief of the Pannocchieschi. Rebelling against the Sienese, Montemassi was conquered again in 1328 by the Sienese led by Guidoriccio da Fogliano after an epic siege which is depicted in the famous fresco “Guidoriccio da Fogliano, Captain of the Sienese, goes to the siege of Montemassi” by Simone Martini present in the hall of the Globe of the Public Palace of Siena.

Characteristic glimpse, Montemassi, Roccastrada, Grosseto. Author and Copyright Marco Ramerini

The small village of houses is dominated by the Castle of Montemassi, an imposing medieval fortification with an octagonal tower that rises on the top of the hill surrounded by olive trees. Even the surrounding village is defended by walls that still surround a large part of the historic center and on which a door opens. The small village has some interesting buildings, including the medieval-era Church of Sant’Andrea Apostolo which is the main church in the historic centre. Among the places worthy of a visit there are also the Baroque-style Church of Santa Maria delle Grazie from the 18th century and the Palazzo del Capezzolo built in the 16th century.

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