Monteprandone is located in a dominating position on the river Tronto Valley.
The most ancient document on Monteprandone’s castle dates back to 1039, when Guido Massaro donated the castle and the church San Nicolò to the Abbey of Farfa.
The castle was then under the rule of Fermo. According to the tradition, the municipality’s name stems from Prandone or Brandone, the name of a warrior who struggled with Charlemagne.
Between the 14th and the 15th centuries Monteprandone widened its boundaries with the annexation of several castles. Its territory was reduced in 1935, when Porto D'Ascoli separated from the Municipality.
The Town Hall currently hosts the Giacomo della Marca’s Library, he was a theologian and saint born in Monteprandone at the end of the 14th century. The collection includes many restored codes with miniatures. Walking in the historic centre of Monteprandone, passing through medieval streets, visitors may admire the Collegiate church San Nicolò, where a beautiful wooden Crucifix of the late 14th century is preserved. Monteprandone offers a rich production of arts ceramics, and the appreciated red wine called Rosso Piceno.