According to historical myth, if you bathed in the swimming pool in the crypt of the San Vincenzo e Anastasio church in Ascoli, you’d be healed of any illness.

Well, that’s what they believed hundreds of years ago. These days, cynics are more likely to tell you the reason pilgrims felt better after a dip in the water was because they were just so dirty they needed a wash. Either way, it’s an entertaining story, and there’s plenty more interesting tales to be told about the sights in this charming hilltop town nestled between the River Tronto and the River Castellano in central Italy.

Like most medieval towns in the region, it was originally a fortress town, with some 200 towers rising from the ground at one point. Nowadays, you can still see about 50 of them, but most have been converted for more modern uses.

Pizza in the piazza

Ascoli’s people’s square”, Piazza del Popolo could rival Venice’s San Marco for ambience and aesthetics. If you stand at one end and look carefully, you’ll notice the rectangular piazza slopes ever so slightly downwards, giving it a somewhat theatrical feel – hardly surprising when you realise Le Marche, the region to which Ascoli belongs, has the largest number of theatres in the country.

To fully savour the atmosphere, do a bit of people watching at the lovingly restored Caffe Meletti, a historical Art Deco café which was once the stomping ground of Ernest Hemingway. Make sure you try out the house speciality of anisette, a licorice-tasting liqueur they tend to like dropping coffee beans into. Don’t leave town without sampling the olive all’ascolana, the region’s favourite appetiser which consists of olives stuffed with meat and then fried.

It’s also worth checking out Piazza Arringo, named after the public assemblies held there since the inception of the city. This square is home to the Sant Emidio Cathedral, most notable for its interesting 14th century crypt, one of the only remaining features of the original church, which had to be rebuilt following a fire in the 15th century. The crypt’s roof features an intricate modern mosaic, added at the beginning of the 20th century to impress a visiting pope. There’s only one fresco remaining from the original church, though it’s badly damaged.

Get artistic

Famous Italian painter Carlo Crivelli found a home in Ascoli in the 15th century after being exiled from his native Venice for committing adultery. He must not have minded, though, as he remained there for almost 30 years until he died in 1493. One of his most famous pieces, the Polyptych, is in the Cathedral’s Cappella del Sacramento, and a number of his other paintings can be found in the Pinacotece, an art gallery inside the Palazzo Comunale. This is a must-see – alongside Crivelli’s works are some 400 other pieces, including paintings by Van Dyck and Rembrandt.

Ascoli also features an impressive 800-seat theatre, built about 150 years ago by local families. Apparently the locals are such staunch theatre-goers even famous Italian opera stars have been scared of taking to their stage for fear of adverse criticism.

The Quintana festival

On the first Sunday of August, Piazza del Popolo plays host to the town’s biggest festival, Quintana. Somewhere between 1000 and 1500 locals come decked out in medieval costumes and converge in the square for this recreation of medieval times, which includes horseback jousting, parades, and various other ceremonies. An evening exhibition, similar to the Quintana, has now been added to the town’s yearly calendar and takes place in July. Between February and March the town holds a large carnival to celebrate the beginning of spring.

A walking tour

Have a wander and you’ll notice distinctly different medieval, baroque and gothic influences throughout the districts. Museums to stop off at include the Archaeological Museum, which houses relics from the Piceni tribes, Ascoli’s first known settlers, and the contemporary art museum. The Malatesta Fortress, the 40m-high Ercolani Tower and the arched Roman Bridge are also worth a look.

Bonus points for: The authentic, non-touristy feel
Loses marks for: Harder to find accommodation
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