There are remains of a settlement dating from theIron Age, next to thefrazione of Casticciano. As for Bertinoro itself, it was probably a strongpoint on the Roman road connectingForlì toRimini. Later, during the barbaric invasions, it was moved to the current location.
In 1177 the castle, already well developed and known asCastrum Cesubeum, housed the emperorFrederick Barbarossa. The named changed toCastrum Brittinori during the reign ofOtto III, becoming seat of the countship.
Colonna delle Anelle ("Column of the Ring" or "Column of hospitality"). It is a column in white stone with 12 rings erected in 1300 by the noble families of the town to show their hospitality. Each one of the rings corresponded to one family, when the foreigners arrived in the town and tied the horse bridles to a ring they selected their host.
Thepieve (church) of San Donato, in thefrazione of Polenta. It became famous as the object of a poem byGiosuè Carducci. It has maintained parts of the original late 9th century edifice.
Bertinoro is home to a "Hospitality Festival". Held in the first weekend of September, it encompasses an entire night of music, dances and events (between Friday and Saturday), some historic reenactments, and the final hospitality rite (Sunday late morning).
In this ceremony anyone can be hosted for meal by a family in the town simply taking one of the envelopes tied to the rings of the Hospitality column (which inside has the name of the hosting family).
Obadiah ben Abraham, also known as "The Bartenura" after the town, or "RAV-רע"ב", an abbreviation for "Rabbi Ovadia [of] Bartenura", was a 15th-century rabbi and commentator of theMishnah.