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There is some uncertainty about the origins of the present-day Rocca dei Bentivoglio, though they predate the year 1000.

Marquis Bonifacio di Canossa (Matilda's father) acquired the castle and the adjoining church of Santo Stefano in emphyteusis from the Bishop of Modena, Guiberto, in 1038. Matilda then inherited the property at the age of nine, but following her death and lack of heirs, the assets would revert to Modena.

In 1218 the first walls of the stronghold were built but by 1247 the castle had already been conquered and besieged by the Bolognese (after a first unsuccessful attempt in 1228), who ordered its total demolition. The fortress was then rebuilt between 1296 and 1311 by Azzo VIII d'Este.

The present clock tower (once a keep for the entrance gate) dates back to 1317.

After 1371 the Marquises of Este also extended the walls of the Rocca, in spite of the current appearance of the building hailing from the Renaissance period, when it was converted into an aristocratic "delizia" for country holidays by Giovanni II Bentivoglio.

Of the original late 13th century nucleus, only the tower on the south side and the adjacent wing remain today.

The interior includes halls still bearing traces of Renaissance frescoes, such as the Sala dei Giganti, the largest room in the Rocca, architecturally divided by columns with depictions of landscapes, probably of Bazzano and other Bentivoglio lands, interspersed with large armed figures and shields showing the coats of arms of the various families.

The adjoining Sala del Camino (fireplace room) displays a decorative motif depicting the Bentivoglio arms framed by the Sforza armorial bearings. Today the Rocca is the seat of the Fondazione Rocca dei Bentivoglio and houses the local Music Centre and the "Arsenio Crespellani" Archaeological Museum, with a wealth of artefacts found in the area, from the earliest Mesolithic settlements to the Renaissance. It is also regularly used for public and private events. The cellar bears traces of the original castle foundations and additionally houses a practical information desk providing tips and documentation on the "Città Castelli Ciliegi" Wine and Flavours Route.

Opposite the Rocca is the Parish Church of Santo Stefano, mentioned as early as 1019, with valuable paintings inside. A large portion of the church and the rectory suffered major devastation during an air raid in 1945 and were rebuilt after the war in a neo-Romanesque style.