Tolentino is a town and comune of about 19,000 inhabitants, in the province of Macerata in the Marche region of central Italy.

The Via Flaminia was an ancient Roman road leading from Rome over the Apennine Mountains to Ariminum (Rimini) on the coast of the Adriatic Sea, and due to the ruggedness of the mountains was the major option the Romans had for travel between Etruria, Latium, Campania, and the Po Valley. The section running through northern Rome is where Constantine the Great, allegedly, had his famous vision of the Chi Rho, leading to his conversion to Christianity and the Christianization of the Roman Empire.