The ancient name Mons Herculis probably derives from an ancient pagan cult dedicated to the demigod Hercules, who is also depicted in the coat of arms of the Municipality in the act of killing the hydra. A stronghold on the border, it was bitterly disputed between Florence and the Papal States due to its important strategic position and its imposing fortification.
Monterchi was profoundly altered by an earthquake in 1917. Most of the buildings overlooking the square no longer exist or have been considerably downsized.
Of the numerous churches that rose inside the walls, today only that of San Simeone remains. It houses interesting works of art including a Presentation of Jesus in the temple by Durante Alberti, a pulpit in pietra serena depicting the coat of arms of Monterchi, close to the ways of the Florentine sculptor Tribolo and three sandstone bas-reliefs from the Marche school.
However, the historic center offers very suggestive views such as the ancient Via de 'Medici, a covered walkway near the square, the panoramic terrace of the Rocca, from which you can enjoy a splendid view of the harmonious Monterchi countryside, and the monastery of San Benedetto, just outside the walls.