This trail has allowed for centuries the passage from the Arezzo to the Perugia area running through the pass between the Monte Maestrino and the Poggio della Croce. The road used to wind down the hill running through Le Contesse and Il Palazzone (where several traces of burials were found) to fork past the hamlets of S.Angelo and Metelliano; one branch used to run on towards Ossaia and Sanguineto (possibly the road followed by Hannibal to reach Lake Trasimeno where the epic battle took place in 217 B.C.) whilst the other used to run along the hill to reach what today is known as Mercatale. This latter stretch of the road used to run by the Etruscan hamlets of Montanare and Rasina, cross the valley of the Niccone, direction Val Tiberina, go over the top of the Monte Maestrino and run past the hamlet located in the area of Pieve di San Donnino, between the valley of the Niccone and the Val di Pierle to finally reach the Mercatale area. This road axis played a crucial role as early as in Etruscan times as it is evidenced by place names you may run across along the ancient route and its surroundings (for example Rasina and Carsena). The Roman-age stone-paving, still visible in many areas, clearly attest to the monumentalization of this road and to the fact that such roads were used as a tool for the “Romanization” of mountain areas as may be inferred from infrastructure, bridges, so-called agri centuriati, archaeological finds as well as place names to be found in these areas including. Place names include Metelliano, possibly named after the local gens Metellia, Sepoltaglia, Spoltaglia, Spelta (most likely referring to the local cultivation of spelt rather than to the burial (in Italian sepoltura) of Roman soldiers killed during the battle against Hannibal). Other interesting place names include the name of the sanctuary of the Madonna del Bagno, possibly referring to an ancient cult of water as well as Campo Romano, Pianello Tre Termine and, in Umbria, Le Bagnaie.
The trail will be recovered through the installation of suitable signs and linked with the existing C.A.I trail n. 50 descending from the top of Monte S. Egidio and servoing as a through route to the Roman road of Torreone. The trail is equipped with basic road signs.