The stunning central Italian city honours its medieval roots by breathing life into many age-old traditions leading up to the main event.
These include a procession for the feast of Sant’Anna in conjunction with the celebration of Sant’Emidio (Ascoli’s patron saint), an athletic flag-throwing competition, and an historical parade in opulent 15th-century costume.
When it comes time for the jousting to get underway, many of the city’s 50,000 residents turn out to cheer on the six knights.
Each knight represents one of Ascoli’s six neighbourhoods: Porta Maggiore, Piazzarola, Porta Romana, Sant’Emidio, Porta Solestà and Porta Tufilla.
They compete on horseback, armed with long wooden lances.
Their task is to manoeuvre on a tight figure-eight shaped track and launch a heavy joust into the target, called The Moor, with exceptional precision.
The victor takes home the Palio, a hand-painted banner, which is then displayed in the heart of the winning neighbourhood.
Ascoli Piceno is the capital of the province of the same name.
Though the city isn't a typical tourist destination, Ascoli’s medieval centre has remained one of the most beautiful and evocative in Italy.
Many of the buildings in the central historical part of the city are built using travertine, a grey-hued stone extracted from the surrounding mountains.
Ascoli's central Renaissance square, Piazza del Popolo, is surrounded by buildings made from this stone.
According to traditional accounts, Ascoli Piceno once housed around 200 towers in the Middle Ages. Today, around 50 can still be admired.
If you're after an authentic Italian experience and captivating architecture, then Ascoli Piceno is definitely worth venturing off the beaten track for.