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Castiglione di Sicilia

Route Sheet

Regional Park of Alcantara, Site of community importance (S.I.C.), called “Natural Reserve Of the Alcantara River” with the following site code I.T.A. n. 030036.

Tipology On foot

Departure Castiglione di Sicilia

Difficulty Intermediate

Length 2,35 km

Altitude 555 mt s.l.m.

Difference 149 mt

Google Earth


Riferimenti cartografici Page I.G.M. n. 262 quadrant IV°, positioning S.E. CASTIGLIONE DI SICILIA - CTR section. 613100 “CASTIGLIONE DI SICILIA”.

Services Equipped areas for visitor stops, informative poster signs for information and directions along the way.


The village is part of the itinerary of the “Borghi più Belli d’Italia (most beautiful villages of Italy)”.

Before the arrival of the Greek in 750 b.C when Naxos was founded, the entire island was inhabited by popolations called Siculi or Sicani. These were advanced civilizations, lived in villages, mastered the art of ceramic, venerated or burried the bodies. Some archeological findings in San Nicola street next ot the Alcantara river, and other founds such as tombs, wine factories and pillboxes, prove that the entire valley was densely populated during the Neolitic and above all during the Bronze Age.
Many caves dug in the sandy ground were designed as living spaces or tombs, like those of Pietra Pizzicata Street, where we can still note a prehistorical village founded by the ancient inhabitants of Castiglione, who had to move to the contemporary townhill due tothe threat of other populations and found a new village.

The Greeks climbed up the Akesine river during the year 710 b.C and settled in Tirone street. Afterwards, they reached the village of Castiglione,occupying it as a fortress. Towards 705 b.C. they headed for Randazzo. During the Roman era, the city at the feet of the hill, was occupied as a campsite, and after by the Greek-Bizantine and Arabs, who bred crocodiles in the Akesine river.

Medieval period

Leone castle reached its major splendour after the Normans fought off the Arabs and consructed the walls and the Cannizzo, an outlook tower at the extremity of the town. In 1233 it was nominated by Federico II,“Animated city” and used as a summer residence. During 1282, after the event of the Sicilian Vespri, the castle passed on to the property of the admiral Ruggero of Lauria, who supported Pietro of Aragona, and then passed on to Giacomo d’Aragona.

In 1297 Federico III of Aragona arrivedpersonallyfor the seige,approaching from Francavilla at south and from Sciambio street at north-west. After a while, the beseiged surrendered, and Federico entered as conquerer through the Gate of the King. After two years, Ruggero reconquisted the city, but only for a brief period of time, because Federico, while heading towards Randazzo came to know that the hill was undefended and beseiged the walls of Cerro plain, conquering it. Due to the declining power of Lauria, the importance of the Leone castle nevertheless began to fade away. It passed over to the feudal property of Giovanni, Duce of Randazzo, and was renamed Castiglione.

Between 1600 and 1900

During this period, the city wasa setting of numerous famines. During 1636 Peculio was established, an institution that enabled the acquisition of wheat that served to support the moments of crisis. Also numerous religious orders were born during this time, as for example the Agostinians who founded the monastery of Mille, the Carmelitans who established the contemporary oratory, the Cassinesi whose abey was positioned next to San Nicola church and the Benedictine who managed an orphanage.

XX century

Castiglione shed blood during the First World War, and even more during the Second World War, when German troups killed 16 civilians and plundered many houses using a tracked machine. In 2002 the President of the Republic offered to the town a bronze decoration for civil merit, as it was the first Italian city suddenly occupied by German troups on their retreat in front of the disembarked Allies.