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Colle di Val d'Elsa is a very old city, probably dating from the Early Middle Ages, although the town was also known with different names from the current one - namely Piticciano and Piticciano Castle.

The early history and origins of the town are slightly unclear but the research tells a fascinating story.

We do not know precisely when the old village around the castle was born, but certainly around the year 1000, because in a document dating from 1007, the noble Wuilla  Aldobrandeschi received certain lands from the Bishop of Volterra, among which Piticciano was mentioned.Other documents mentioning 'Piticcianum' date back to the 12th century. We know from these that Colle di val d'Elsa was rightly called Piticciano, and that from 1183 we know that the city was also called Colle, because, in a Bull of Pope Lucius III (1110-1185), who gave the abbot of “Santa Maria di Spugna” many goods and lands, it was said that some of these assets were close to the 'Castellum Piticcianum quod Colle vocatur'. ie Lucius III wrote that the possessions were close to the “Piticciano Castle, which is called Colle."

So towards the end of the twelfth century Colle di Val d'Elsa was already known by that name - likely the same 'Castrum Collis' in Tuscany mentioned in 801 by Charlemagne (742-814). Another important historical fact is that, around the year 1000, Piticciano was probably a fiefdom of the powerful Counts Aldobrandeschi; in fact, Countess Wuilla was the widow of Count Rodolfo and mother of Hildebrand Aldobrandeschi. Recent historical studies have indeed shown that, in the early eleventh century, Colle di Val d'Elsa was contested between the Aldobrandeschi and the Bishop of Volterra. Towards the end of the twelfth century, however, “Colle di Val d'Elsa” fell in the orbit of the Florence power, and it was usually called "Castrum Collis", and, more simply, "Colle".

It was only in the nineteenth century, “Val d’Elsa” was added to the name, to indicate the area where the city stands, i.e. along the River Elsa, left tributary of the River Arno.

Placed near the famous trade route, the Via Francigena, it quickly developed considerable industrial activities and a powerful mercantile bourgeoisie, as witnessed by the Tower-Houses of wealthy merchants of Colle and the massive walls of the city, which was extended until to encompass the surrounding villages. Under the Medici's domination, Colle knew great economic prosperity, because of its manufacturing and development of iron working.

By the fifteenth century Colle was a remarkable city, which could also withstand sieges by powerful enemies: in 1478 it was in fact attacked by the armies of the Pope and King of Naples, but it managed to resist and reject the enemies. After this event, the city strengthened the walls further, also building the so-called Porta Nuova (a work by Giuliano da Sangallo (1484-1546)), to replace one destroyed during the siege. The power of the wealthy merchant bourgeoisie of Colle manifested itself even more with the construction of magnificent palaces, like those built by Francesco Campana (1491 ca-1546), the Secretary of Cosimo I de Medici (1519-1574).

Francesco Campana also promoted the construction of other important buildings and churches, like the Palace of Justice, Hospital of San Lorenzo, Cathedral and Bishop's Palace. From the sixteenth to the eighteenth century, Colle witnessed a continuous economic growth, giving impetus to the manufactures of the city (the wool, paper, glass and iron industries) and some agriculture-related activities.

During the nineteenth century, Colle expanded even more, at the expense of the old walls, now almost completely lost, while it developed the glass industry, which is still one of the attractions of the city. Despite this continued expansion the old Town still retains a significant amount of evidence of its past.