The perfect meeting point between hill and valley, between Pistoia and the Prato-Florentine area, the city of Montale is to this day marked by the strategic importance that it had all throughout history as a military and agricultural key point. The area of Montale as we know it today was originally placed under the control of the influential House of Guidi, already rulers of the neighboring Montemurlo since the ninth century. The first settlements of roman origins were built around the Hellana station on the Cassian way. The area was slowly populated from the tenth century in the area of the church of San Giovanni Battista, the village of Tobbiana (first mentioned in the hystorical archives in 1079) and, in the early thirteenth century, Montale Alto. The valleys became habitable only after the reclamation of the land and the construction of water canals.
The domain of the Guidi underwent moments of great contrast. The family went to war with the Florentines and, subsequently, with the city of Pistoia, which won and took over the territory of Montale. It was precisely the inhabitants of Pistoia that in 1203 started building the fortress that would from thereon be known as Montale. It was placed at the foot of a steep hill, on the other side of the Montemurlo Castle, which was still a threat for Pistoia on the eastern boundary of the city. A few years after its construction, Montale was severely damaged by the Florentines, who, in subsequent peace agreements signed with the approval of Pope Innocent III, even demanded its demolition and the definitive relocation of the population in Montemurlo. However, this condition was never put in practice: the podestà of Pistoia worked with incentives patronizing land and houses. In this way he managed to keep Montale populated, and he maintained the garrison of such a strategic area.
By the early fourteenth century, however, it became clear that the fate of Montale was inextricably linked to the political turmoil that at the time agitated Florence and Pistoia. As the war between White Guelfs and Black Guelfs worsened, the castle of Montale went under the control of the Cancellieri family, one of the ruling houses of Pistoia. In 1303 Pazzino di Jacopo de’Pazzi managed to conquer Montale, which was assigned to Florence with a final armstice signed in 1306. It isn’t clear whether at that point Florence decided to destroy the fortress of Montale but it is documented that in 1313 it shifted back under the jurisdiction of Pistoia. A dozen of years later the duke of Lucca Castruccio Castracani consolidated the defensive front against Florence, before ordering the definitive destruction of the fortress, probably because of the gradual loss of its strategic importance.
From 1351 Montale was controlled once more by the Florentine Republic, which had assigned the city of Montale and the nearby town of Agliana to a mayor who was, in his turn, under the command of Florence. In 1402, Pistoia established its final domain on the town and Montale became the new sede podestarile (with Tizzana, Serravalle and Larciano) whose duty was to govern and survey the area that went from the Apennine mountains to the Valley to the Bisenzio and all the way to the hills of Agliana, where there was the important custom-house for duty collection. The administrative relevance of Montale was destined to grow and develop in time.