The name of this quaint town is derived from the name of a frankish knight appeared in the Piceno in 800, his name was in fact Prandone (or Brandone). This knight united all the dispersed populations of the region and built them the Mons Prandonis (or Brandonis) castle. The community lived under protection of Farfa monks until 1292, when it was forced to treat the submission to the city of Ascoli, however the submission would guarantee the expansion to the sea and on the other hand Asculum had acquired an another ally in opposition to Firmum. In 1333 Monteprandone begins to enlarge its territory by conquering the neighboring castles, such as: Monterone, Monte Tinello (or Dinello), Monticello and Montecretaccio; it is from this expansion that was born the emblem of the town still in force, representing just five hills. In 1393 Monteprandone came under the protection of Pope Bonifacio 9th that facilitated the annexation of the territory of Porto d’Ascoli, finally bringing the borders of the community to the sea. These territories remained stable and unchanged even after two major wars in wich Monteprandone was found in the middle; the first in 1490 when Offida ally of Fermo attacked the city of Ascoli in any way, and the second in 1557 when war broke out between France and Spain, and because of the alliance of Pope Paul 4th the battle with the french moved in the Papal States, where exactly was the town. However, it was only in 1935 that Monteprandone lost Porto d’Ascoli, following the decree of king Vittorio Emanuele, who handed it to San Benedetto, a city that has always craved this fraction, demonstrates this fact also a letter of 1934 that mayor Francesco Cossignani wrote to the prefect of Ascoli.