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The hill of Oliveto, already inhabited since prehistoric times and then occupied by Etruscan and possibly Roman settlers, was originally called Casale Sociorum, later to become Monte Oliveto due to the peculiar vegetation of the area with thousands of olive trees. In 776, the territory of Oliveto was donated by the Lombard dukes of Persiceto and included in the fiefdom of the abbey of Nonantola until the Olivetans became independent in 1131, remaining a free commune for about a century before freely deciding to pass to the commune of Bologna. In 1428, the Olivetans and the Bolognese once again opposed Papal rule, who sent Caldora's mercenary troops to plunder the town and its castle.

Only a few traces of the old Oliveto buildings have been preserved: vestiges of the 11th-century castle and the oratory of Santa Maria delle Grazie (recently restored and already in existence in the year 1000) and the bell tower of the frontless church of San Paolo, home to an altarpiece attributed to the 17th-century Bolognese painter Elisabetta Sirani. However, the most important and best-preserved building is the so-called Cà Grande dell'Ebreo, seat of the Jewish community and the first bank in the area. The walls of this imposing mediaeval complex still bear an old terracotta plaque with a Latin inscription reporting the beginning of the site costruction "built in 1410 by Salomon Mathasia".

Just at the gateway to the village we find the "Bronzina", a heavily altered late-Medieval building that served as a lodging for the Grandees of Spain in 1527. A legacy of their passage is the Spanish-inspired festival that takes place annually in March, the 'Festa della Saracca'. The celebration is dedicated to the 'Funerale della Saracca', i.e. the funeral of the dried sardine, buried at the foot of a wooden cross to symbolise the end of winter shortages and the beginning of spring.