Testimony of human presence during the classical era recently emerged from Etruscan civilization tombs in the old town and from the discovery of a Roman villa dating from the Republican age.

The place was known as Mansio ad Arnum, as evidenced in the Tabula Peutingeriana, and it is probable that in the area there was a bridge that, during ancient Rome, permitted the crossing of the river Arno.

Beginning on the 13th century AD, the town of Montelupo Fiorentino is destroyed by the Florentines, whom, on the same site, built a walled castle - true symbol of their domination in the territory.

The production level was such that required an “Editto del Potestà” (Edict) to prohibit that the huge quantities of waste and processing residues were thrown in the adjacent Pesa River, so to avoid its stream to be diverted.

Some pieces of Montelupo Fiorentino pottery have been found in archaeological sites in Central America related to the first European settlement in the area, as well as in the Philippines and Scotland.

A particular specialty was the 17th century "Arlecchini" style, a satirical depiction of different professions and national types, including the fearsome Landsknechts, German mercenaries who fought on behalf of Charles V, Holy Roman Emperor.

In 1977, the volunteers of the "Archaeological Group of Montelupo Fiorentino”, discovered inside the castle, overlooking the medieval village, the mouth of a large well (the well of washing), filled with fragments of pottery from the town’s kilns.