The co-patron of Montecosaro is Our Lady of the Annunciation, celebrated on 25 March with the Festa e Fiera dell'Annunziata, near the Basilica di Santa Maria Piè di Chienti; the town's patron, Saint Lawrence, is instead celebrated on 10 August.
According to local legend, the name Annunziata comes from the pardon of a pope who was thrown into and buried in a well of the monastery and rose again after three days, giving rise to the good omen tied to the feast. In summer, the MIND Festival is also held, a music event born in 2011 in Montecosaro Scalo, which over the years has hosted nationally and internationally renowned artists.