Guidoriccio da Fogliano at the Siege of Montemassi (Italian: Guidoriccio da Fogliano all'assedio di Montemassi) is a fresco on the west wall of the Sala del Mappa Mondo in the Palazzo Pubblico in Siena. It shows the commander of the Sienese troops, Guidoriccio da Fogliano, on horseback against the background of a landscape depicting the siege of Montemassi.
It has long been assumed that the work was painted in 1330 by Simone Martini (1284 -1344). This dating made it one of the first secular portraits and one of the first monumental landscape paintings. It is widely considered a masterpiece of European painting.
In the center of the fresco, Guidoriccio da Fogliano is depicted on horseback, in profile holding a marshal's staff. To the left is Montemassi on a hill surrounded by defensive fortifications. To Guidoriccio's right is a siege machine with the flag of the Sienese Republic flying. On the right side of the image, a mountain rises at the foot of which are tents. Again, white and black flags and pennants can be seen. At the bottom of the fresco is written in Roman numerals the year of the conquest of Montemassi by the Sienese troops: MCCC.XX.VIII (1328). The castle of Montemassi is clearly recognizable in the Guidoriccio.
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