Mentioned for the first time in 1338, Caudino was one of last castles built by Rocca Contrada. It was an important bastion constructed to defend the territory facing Pergola, west of Arcevia. It still boasts a picturesque entrance gate and a part of the ancient fortified structure. A memorable battle was fought not far from here between the Guelph and Ghibelline forces as they struggled for control of the area. At its centre, next to the old bell tower, is the Church of S. Stefano, which was reconstructed in the XVIII century and is home to a XVI-century fresco depicting the Madonna of Loreto.