According to some sources the origins of the town can be traced back to the Neolithic Age, and it is assumed that there were settlements dating as far back as to prehistoric times. In Roman Times San Calogero was cut off from the world due to its distance from the Via Popilia, which linked Rome to Reggio di Calabria. According to other sources, the origins of San Calogero can be traced back to the 10th century A.D. when a group of serfs settled around the convent dedicated to Saint Opolo. Later, possibly in the 9th and 10th centuries, groups of Saracens sailing from the south-east set foot on the coast raiding and pillaging. This caused coast-dwellers to take to the hills.


At some later date a group of serfs settled around the Benedictine convent dedicated to Saint Opolo. The convent was probably founded during the 9th or 10th century A.D. In the centuries that followed, San Calogero was ruled by the Normans and the Bourbons first, and local landowners such as the Ruffos, the Maritanos, the Morincolas and the Mottolas later. The town is also said to have been destroyed by an earthquake in 1783: later it was completely rebuilt.

The main historical and archaeological sights in San Calogero include:
• the remains of the Basilian monastery built in honour of S Opolo in the X century;
• burial niches which bear witness to Saracen culture and influence;
• the remains of the water mills;
• Madonna delle Grazie church (this simple shrine was built at the beginning of the 19th century by baron Mottola and is located in the Castello area).