The trail can be considered an extension of the route from Ponte to Umbertide and is graded medium because of various hills and dales and the climb to the centre of Montone. Apart from one particularly steep stretch, most of the trail is easy and even the least well trained cyclists can finish it if they are little patient

Starting from Piazza Mazzini the trail goes towards the Tiber river then follows a dirt road up the valley towards Montone. It follows the Tiber for about three kilometres before turning inland at km5,5 to the main road between Montone and Umbertide. From here, it turns left, then right at km 5,8 along a country lane to San Lorenzo. At km 6,2, it leaves the sealing and goes along a dirt track in the middle of the fields where there is a good view on the left of Montone. 

At km 10, after a short climb, it goes along a sealed lane which returns to the main road (km 11,5) after a short descent. After crossing the road (beware of traffic), it enters another dirt road and climbs towards Montone: this is the most difficult part of the trail, because the last few metres are very steep and will force less expert bikers to dismount.

Back on the sealing (km 12,3), the climb is gentler, and in less than a kilometre the trail reaches Montone, where the beautiful historical centre and views of the valleys below make a visit well worthwhile. From here the trail descends towards Umbertide, meeting the dirt road again at km 18,7 after turning right at a bend to the left.

From here, the trail returns to the Tiber (km23) through a labyrinth of sealed and unsealed lanes through flat land. It then returns along the first part of the route back to Piazza Mazzini, which is close to the Rocca and the town centre.

As well as the historical centre of Umbertide with its superb medieval Rocca, already mentioned in Trail n.4, seeing the walled village of Montone, is a must. The church of San Francesco (XIV century), which has a polygonal apse and nave, is the most important building in the town. In the historical centre is also the former convent of Santa Caterina, now hosting the town’s historical archives (archivio Storico Comunale), amongst the most important in Umbria for its rich heritage of documents. Another important religious building is the pieve di San Gregorio, the oldest church in Montone, constructed in romanesque-byzantine style in about 1000 a.d. Just outside Montone is the Rocca d’Aries, an imposing castle that has been recently restored. Not far from Umbertide is the Civitella Ranieri castle, also worth a visit. The natural scenery around the Tiber river and the wood-covered hills is also beautiful to see.