Ascoli had its port already in the Middle Ages!  This story starts indirectly in 1211, when Ottone IV gave to the town of Fermo the rights to the coast of the Potenza river till Tronto river.

In 1245 the Imperator Federico II granted to Ascoli the port and the coast between Tronto river and the rio Ragnola. Ascoli strengthened immediately this part of the coast, but Fermo reacted  by  assaults and incursions.

In 1323 the Pope Giovanni XXII granted to Ascoli the part of the coast from Ragnola to Tronto to construct a fortressed and well equipped port to receive vessels and goods and assured to the town the permit of the dominator of  the Adriatic Sea, Venice that in 1326 signed agreement with Ascoli . The Venice people could move free in Ascoli territory , while the merchants of Ascoli could export products in all Venice lagoon.

So in 1326 the port of Ascoli was in function: situated under the Monte Cretaccio Fortress , had two big towers and seven towers decorated by seventy battlements. An important construction that did not have unfortunately long life: in 1348 the Fermo troupes, directed by Gentile da Mogliano, destroyed the fortress as told by an inscription on two stones that the Fermo people have taken away from the building of Porto d’Ascoli and walled as trophy in their church of S. Agostino.

Later , in 1351 the two rivals stipulated peace and the property of the port was kept  by Ascoli, but Fermo could use it for sailing and trade .