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The Val di Pierle, also know as Val del Niccone from the stream which runs through it, lies to the east of the Val d'Esse and is the most easterly part of Comune of Cortona. Amongst the valleys of the Comune this is the largest and the most densely populated. No documents exist to say when "life" began in this valley but there has been since roman times, a road link with the Val d'Esse (Cortona) across the ridge which separates the two valleys. The road passes near the church of Montanare (1200) dedicated to St. John The Baptist, climbing steeply towards the ridge between Poggio della Croce and Monte Maestrino. The ancient paving stones have been scattered and broken and are found every now and then at the edges of the nearby fields. The line of the road is still visible but at some places it is barely passable having been by worker farmer machine and by general lack of interest. Toward do the ridge there are some paved sections more and less visible. Years ago it was easy to follow the road but now it is very difficult to find these paved sections. The descent follow the southern flank of Monte Maestrino to above the castle of Pierle but does not go directly to the castle because of a deep gully to the right of the road which therefore bears left towards the cementry. In fact it is not possible to follow the road from Monte Maestrino to Pierle because the terrain is difficult and the road is completely overgrown. However the roman road is not the only remainder of the roman presence in the Val di Pierle. There are some inscriptions and a funerary urn at San Donnino, a funerary "stele" at Pierle and remains of houses and cisterns for water collection. We have to way of knowing whether by these "unknown" inhabitants of the valley took part in the famous battle of Trasimeno between Hannibal and the Romans in 217 b.c. but it is possible that a skirmish or two might have taken place here. It is worth bearing in mind that Romans army came from the Adriatic and it is very easy likely that in order to reach lake Trasimeno it would have passed through the valley. Besides evidence of the Romans there are also signs of Etruscan settlements.