The first settlers of the province were located on the banks of River Tronto by the Picentes tribe. It was later conquered by the Romans and became known as Asculum Picenum by 268 BCE. From 91-88 BCE the Picentes revolted against the Romans and attempted to re-claim the land, but Gnaeus Pompeius (Pombey) Strabo besieged and sacked the city. The town of Ascoli Piceno managed to revive, but after the 476 collapse of the Roman Empire, it was conquered many times. King of the OstrogothsTotila invaded the town in 545. Ascoli Piceno was then under strong control from the church and was made free in 1185, but the bishop declared it under his control in 1212.
The town was sacked by Frederick II, Holy Roman Emperor in 1242; it later recovered but fought against Ferno from 1256 until 1504. It joined the Kingdom of Italy in 1860 with the rest of the region, and was saved from bombardment by Pope Pius XII in World War II. The capital of the province, Ascoli Piceno, was constructed at the confluence of the Tronto.