After the Sicans, the rock and the surrounding lands were certainly inhabited by the Phoenicians, undoubtedly not indifferent to the strategic importance of the place. They came to Sicily from actual Palestine around VIII century B.C., and imported their customs and religion here, human sacrifices to their divinities included. Their bloody cult is also witnessed in Mothya, and it survived during the Sicilian Greeks' expansion on this area. In fact, groups of Greeks moved here from Eastern Sicily around the V century B.C., attracted by the three "virtues" (trias kala in Greek) of the land: fertility of soil, richness of water and a privileged position. The settlement was therefore named Triokala. The cult of Greek god Kronos also requested the sacrifice of small children, so the Phoenician rites survived until Christian age.
Around 258 B.C. during the First Punic War, the Romans destroyed Triokala, and the inhabitants moved to the near Trokalis, actual S. Anna, 7 km away. The ancient Inycon/Kamikos/Triokala was again inhabited during the Slave Wars, when bands of rebel slaves chose the rock to resist the siege of Romans, between 104 and 99 B.C. The last 1000 slaves surviving to the siege finally surrendered, and were brought to Rome to fight as gladiators. But once arrived there, they killed one another to escape their sad fate. The rock was again deserted for a long time. [ + ]
Under the Roman and the Byzantine rule Trokalis was tributary of the Empire, and the whole territory was very impoverished and couldn't have a proper development. The only happy episode in this sequence of dark centuries is the arrival of S. Pellegrino, who eradicated pagan cults and spread Christian religion. A legend wants him victorious over a cruel dragon (symbolizing pagan religion) in the cave of the omonymous convent of S. Pellegrino, where a stone altar for human sacrifices is still visible. In the IX century A.D, the rock was used by the locals to resist the incursions of Saracen pirates, and when the Arab finally occupied Sicily, between 860 and 1091, the territory took the name of Qaliat al Ballut and became Muslim.
In 1091, Count Roger of Hauteville from Normandy chased the Arabs from Qaliat al Ballut, and they moved to the near Sciacca. The Normans left many traces of their presence, from the Castle (now ruined) to several churches dating back to the Middle Age, and the town walls, of which two gates survive. When the Hauteville dynasty ended without a male heir of age, Queen Sybil - mother of William III and regent in his name - had to resist the attacks of Emperor Henry VI of Swabia, retreating in the Norman castle. The Emperor finally had Queen Sybil leave the castle with a trick, accused her of arranging a conspiracy against him, and imprisoned her and William III, so acquiring the crown of Sicily.
Later, at the time of the Vesper Wars between the French house of Anjou - supported by the Pope - and the Spanish house of Aragon - supported by Sicilian nobles - Caltabellotta was chosen to have Charles of Valois and Frederic III of Aragon signing the famous Peace Treaty in 1302, which put and end to the Wars and proclaimed Sicily's independence from the house of Anjou until the end of Aragonese rule, in 1414.
Caltabellotta had been designated a feud since 1134, and it included a great number of territories and villages of actual Agrigento province, belonging to the Sicilian Counts Peralta since 1336. Later, the feud grew even bigger, thanks to the lucky union with the Dukes of Randazzo, who brought innumerable feuds in central and Eastern Sicily as a dowry. Caltabellotta was therefore a very powerful and rich county at that time. This extensive property passed from the Peralta to the Luna family in 1400, and after a long bloody series of family revenges between the Lunas and the Perollos - ending with the suicide of the last Count Sigismondo Luna - the town of Caltabellotta became a single municipality, as the other villages belonging to the county. From that moment on, the town has shared the destiny of the rest of Sicily: the Spanish rule, the Savoy and the Hapsburg, and finally the Bourbons rule, ending with the unification of Italy in 1860, and the institution of our actual Republican rule in 1946. Today, Caltabellotta can still boast a rich territory and a privileged position, and its past glory still hovers misteriously in the thin air of its rock.
Lots of legends still mention Caltabellotta: ancient figures of female oracles exercising their rituals on the rock, and the Grail and Antigrail legends. It seems the Templars came here to hide the Grail they had brought from Jerusalem, and a count Landolfo from Capua killed king Charles the Bald - the Grail keeper - to use it for evil purposes. This is the subject of a medieval text, the Parzival by Wolfram from Eschenbach. Count Cagliostro is said to have been in Caltabellotta in the XVIII century, to capture the magic powers of the place for his own purposes, while the English magician Alistair Crowley came in the 1920's to look for the Antigraal, which he thought was kept in town. You can start your exploration from the Mother Church, the Church and convent of Saint Pellegrino, the churches of Sant Salvatore, Saint Lawrence and Saint Augustine, the churches of the Pity and Saint Mary of Mount Carmel, if you are interested in arts and traditions.
You can't miss the ruins of the Norman Castle and Saint Cono Caves, and the archaelogical site of Saint Benedict, of course. Lots of naturalistic excursions can start from here as well: the Sican Mountains, the Sosio river area, Torre Salsa Natural Reserve, the white cliffs of Eraclea Minoa and Scala dei Turchi, to mention just a few. Sciacca, Agrigento, Selinunte and Eraclea Minoa are strongly recommended, if you're interested in cultural trips, and local products (high quality olive oil, wine and cheeses) are surely of great culinary interest.