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In pre-historic times the area was inhabited by the Piceni (9th-3rd centuries BC). After the Roman conquest, it received the status of urbs urbana (built city) in 268 BC. In the 5th century it was captured by the Visigoths.
In the 12th century, it was a free commune, thwarting the attempts from Fermo to capture it. In the 15th century it was acquired by Francesco Sforza, who fortified it; in 1663 it became part of the Papal States, to which (apart the Napoleonic period) it remained until 1860, when it was annexed to the newly formed Kingdom of Italy.
- Mura Castellane (walls), built by Francesco Sforza in 1443
- Porta del Pero and Porta San Basso, the ancient entrance gates
- Ghetto degli Ebrei, quarter of the Jew population in the 16th century
- Communal Palace (14th century), in Romanesque-Gothic style
- Pinacoteca (art gallery)
- Archaeological Museum, in the church of St. Francis (12th century)
- Inside one of the most important churches of the whole town, St. Maria dei Letterati which is situated next to the central square, are located various paintings and frameworks planned and carried out by the native-born painter Vincenzo Pagani.