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Passed Tolentino, the Via Lauretana, today traced by the Provincial Road Val di Chienti, continued towards the“Castello della Rancia”. Near Montemilone, today’s Pollenza, once stood the Osteria del Chienti, attested since the 18th century. Parallel to the river, the route skirted the Osteria di Sforzacosta, now in ruins, then left the plain to climb uphill , where Macerata stands.
After passing the suburban villa of the Costa counts, the pilgrims following the "climb of Sforzacosta" arrived at the hill called Santa Croce, where in 1505 the convent of the Minor Observant friars of the same name was founded, then they descended to Porta Romana.
Just before the road crosses the railway, the Contrada di Fontescodella opens up, which recalls the water source of the same name, which crosses Porta Montana, passing next to the source of Santa Maria Maddalena with the nearby church of the Torresana in the greenery. You eventually reach the Dominican convent of Santa Maria delle Grazie, where the Convitto Nazionale is located today. From the convent of Santa Croce, of which only the church now remains, the Via Lauretana descended along the road called degli Zoccolanti, in memory of the friars who moved there from the little church of Pietà, still present today along the “via alla Villa Potenza”. Here a new church was built at the beginning of the 16th century, for this reason it was called the “Church of Pietà Nuova”.
Along the avenue, which ended with the “Tre Archi”, or Porton Pio, a mighty structure with three arches erected in 1625 in honor of Cardinal Pio di Savoia, now no longer in existence, in 1650 the Municipality of Macerata allowed the construction of twelve small chapels built with the stations of the Via Crucis.
Beyond the Three Gates ran the Porton Pio road, opened in 1579, where the horse post station was located and on which the village was shaped from 1882 named after Cavour, once it was called Boncompagno in honor of Gregory XIII, who reigned at the time, as well as the gate at the end of the road, known as the Roman gate, designed by Pompeo Floriani which marked the main entrance to the city."
