Located in the crypt of the Cathedral, the Oratory of San Giovanni Decollato traces its origins to the mid-16th century, when the Confraternity of Mercy and Death established its headquarters there. The Latin inscription "Templum Societatis Misericordiae" (Temple of Mercy) can still be read on the architrave of the portal, a reminder of its ancient function. In the 17th century and subsequent centuries, the oratory was enriched and transformed, until, between 1972 and 1974, it became the Tomb of the Bishops of Ripatransone, with the funerary monuments of four local prelates. Above the stele stands a dramatic polychrome Crucifixion by the Ascoli ceramist Giuseppe Marinucci, while behind the high altar is a wooden Crucifix from the 17th-18th century. Among the furnishings, the left altar, dedicated to the Virgin of Sorrows, stands out. It is attributed to Giovanni Moschetti di Montegiorgio and embellished with a Dead Christ sculpted by Giuseppe Manzo di Lecce. The walls feature the Stations of the Cross from 1974, elegant 19th-century gilded appliques, and a small canvas by Luigi Corsi depicting the Virgin of the Seven Sorrows. The sacristy contains engravings by Giuseppe Capparoni dedicated to the Via Matris and, at the back, an 18th-century painting by Pietro Capocasa of the Dead Christ supported by angels. The artistic heritage is completed by the Verati liturgical organ from 1909, restored in 2003, and a more recent canvas by Mario Vespasiani depicting the procession of the Dead Christ, testifying to how the oratory remains a living place of faith and collective memory.

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