Ascoli was founded by an Italic population (Piceni) several centuries before Rome's founding on the important Via Salaria, the salt road that connected Latium with the salt production areas on the Adriatic coast. In 268 BC it became a civitas foederata, a "federated" city with nominal independence from Rome. In 91 BC, together with other cities in central Italy, it revolted against Rome, but in 89 BC was reconquered and destroyed by Pompeius Strabo. Its inhabitants acquired Roman citizenship, following the developments and the eventual fall of the Roman Empire.
In 1189 a free republican municipality was established but internal strife led dramatically to the demise of civic values and freedom and to unfortunate ventures against neighboring enemies. This unstable situation opened the way to foreign dictatorships, like those of Galeotto I Malatesta (14th century), initially recruited as a mercenary (condottiero) in the war against Fermo, and Francesco Sforza. Sforza was ousted in 1482, but Ascoli was again compelled to submit to the Papal suzerainty. In 1860 it was annexed, together with Marche and Umbria, into the newly unified Kingdom of Italy.
The monumental entrance of Julius II in the church of San Francesco
The central historical part of the city is built in marble called travertino, a grey-hued stone extracted from the surrounding mountains. Its central Renaissance square, Piazza del Popolo ("Square of the People") is considered one of the most beautiful in Italy. According to traditional accounts, Ascoli Piceno was home to more than two hundred towers in the Middle Ages: today some fifty can still be seen.
The Gothic-style church of San Francesco (begun in 1258). The dome was completed in 1549. In the side portal is the monument to Pope Julius II, while the central portal is one of the finest examples of local travertine decoration. Annexed to the church is the 16th-century Loggia dei Mercanti, in Bramantesque style of the Roman High Renaissance.
The Romanesque San Vittore (documented from 996) with a low bell tower.
St. Augustinus (14th century). Built with a single nave, was enlarged with two aisles in the late 15th century. The rectangular façade has a 1547 portal similar to that of St. Emidio. The convent houses the Town's library, the Contemporary Art Gallery and an auditorium.
The convent of San Domenico, now a school, has a Renaissance cloister with 17th-century frescoes.
San Tommaso (1069), housing numerous art works and built with parts from the neighboring Roman amphitheater.
The Franciscan convent, of which two noteworthy cloisters remain today. It was once a prestigious center of culture, whose students included Pope Sixtus V.
The Palazzo dei Capitani del Popolo ("Palace of the People's Captains"). Built in the 13th century connecting three pre-existing edifices, it was the seat of the podestà, the people's captains and, later, of the Papal governors. In the 15th century the southern side was enlarged, and, in 1520, a Mannerist façade was added in the rear side. In 1535 it underwent a general renovation, and in 1549 a new portal, with a monument of Pope Paul III, was added.
The Porta Gemina ("Twin Gate"), an ancient Roman gate from the 1st century BC, through which the Via Salaria entered the city. The ruins of the ancient theater are located nearby. It had two passageways, each 5.70 m tall and 2.95 m wide
Porta Tufilla, a tower-like gate built in 1552-1555. It is annexed to the Ponte Tufillo, a medieval bridge built in 1097 over the River Tronto.
Ponte di Cecco (Cecco Bridge), over the Castellano, recently identified of being of Roman Republican origin
Ponte Maggiore ("Great Bridge"), of medieval origin
Lombard Palace and the Ercolani Tower (11th-12th centuries)
The Loggia dei Mercanti, a 16th-century portico annexed to the church of St. Francis. It was commissioned by the city's wool traders guild and finished in 1513.
Fortezza Pia, a fortress commanding the city rebuilt in 1560 by Pope Pius IV (whence the name).
Edicola (monumental niche, once housing a Madonna image) of Lazzaro Morelli, a 1639 architecture attributed to sculptor Lazzaro Morelli, a disciple of Gianlorenzo Bernini.
Grotte dell'Annunziata ("Grottoes of the Annunciation"), a large portico with niches from the 2nd-1st centuries BC, whose original function is unknown (it has been suggested that they could be barracks or slaves dwellings, or a fortified palace)
In Castel Trosino, not far from the city, in 1893 a rare 6th-century Lombardnecropolis was found.
Recent industrialization has brought to Ascoli several Italian and multinational companies (YKK, Manuli, Pfizer, Barilla) but the bulk of the economy is made up of small and medium sized enterprises and by those providing professional services to the area. Agriculture is still important (wheat, olives, fruits).
The main festivity is on the first Sunday in August. The historical parade with more than 1500 people dressed in Renaissance costume is held in celebration of Saint Emidio, protector of the city. The parade is followed by a tournament, called Quintana, in which six knights, each competing for one of the six neighborhoods in the city, ride the course one after the other trying to hit an effigy of an Arab warrior. Strength and ability are necessary for the knight to win the palio or grand prize.
The town is also home to Ascoli Calcio, currently in the Serie B. The team is also known as "Picchio" (Woodpecker), in honour of the bird shown on the Marche's Flag. Ascoli Piceno was founded by ancient italic people after following a woodpecker that signed them the place.
Bivio Giustimana, Campolungo-villa sant'Antonio, Caprignano, Carpineto, Casa circondariale, Casalena, Casamurana, Case di Cioccio, Casette, Castel di Lama stazione, Castel Trosino, Cervara, Colle, Colle san Marco, Colloto, Colonna, Colonnata, Faiano, Funti, Giustimana, Il Palazzo, Lago, Lisciano, Lisciano di Colloto, Montadamo, Morignano, Mozzano, Oleificio Panichi, Palombare, Pedana, Piagge, Pianaccerro, Poggio di Bretta, Polesio, Ponte Pedana, Porchiano, Rosara, San Pietro, Santa Maria a Corte, Talvacchia, Taverna di mezzo, Trivigliano-villa Pagani, Tronzano, Valle Fiorana, Valle Senzana, Valli, Vena piccola, Venagrande, Villa S. Antonio.