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The history of Pennabilly is rich and complex. Its name derives from the union of the castle of Penna with that of Billi. The town was later enlarged and fortified by the lords or Carpegna, the Malatestas and the Montefeltros. It become a real "city" when it was chosen as the seat of the Montefeltro Diocese during the 16th century as well as of many admi-nistrative institutions. Pennabilli is still immersed in its medioeval atmosphere and there are numerous testimonies of its glorious past in the original plan of the old town and the old Gates: Porta Malatesta, Porta Carboni, Borgo S. Rocco, the Sanctuary Madonna delle Grazie.
Right in the middle of the town the main square is surrounded by the Palazzo della Regione, the 17th century Town Hall, the Merchants' Loggia and the Cathedral. A remarkable artistic heritage collected from all the old abandoned churches all over the Montefeltro region is now preserved in the Diocesan Museum. It also contains numerous examples of sacred arts. Today Pennabilli's most important event is the annual National Market Exhibition of Antiques, which is of national importance and attracts crowds of visitors, who can also admire many particular "inventions" like for instance the "Garden of forgotten fruits and vegetables" and "the Street of the Meridians" the "Refuge of lost Madonnas" and Begni Park.
Pennabilli is a convenient and well organized resort famous for its genuine cookery and for the varied country itineraries: to Sasso Simone, to the Simoncello, on Mount Carpegna, to Lake Andreuccio and for historical itineraries: like the walk to the ancient Romanesque church delle Pantiere at Ponte Messa or to the ruins of Scavolino Castle, to the Tower of Bascio and to the Monastery of Maciano.
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