Cupramontana was founded probably in the fourth to fifth centuries B.C. and took its name from a temple that stood there dedicated to the goddess Cupra. The town was mentioned by Pliny the Elder and Ptolemy in the Augustan age, as one of the ancient cities of Piceno, and therefore was an important town in Roman times.
Devastated during the Greek-Gothic war, the town was abandoned and its ruins were later used for the construction of firstly fortifications, and later a castle, which was built close to the ancient town but higher on the hill and which was then given the name of Massaccio. From the seventh century Massaccio was part of the Lombard Duchy of Spoleto. From the thirteenth century, Massaccio was merged into the county of Jesi becoming until its dissolution in 1808, the most important centre of the county. In the fifteenth century Massaccio was one of the strongholds of the heretical sect of the "Fraticelli"; in 1444 it was occupied by troops of Francesco Sforza and in 1517 it was looted by the militia of the Duke Francesco Maria della Rovere.
Then there followed a long period of peace, during which the town experienced strong population growth combined with cultural development. In 1747 the site of the ancient Roman town of Cupramontana was rediscovered, close to Massaccio. The discovery was made after the correct reading of an inscription on a tablet which had been discovered in 1718 in the archaeological zone. The tablet, referring to 'Cupra Montana' by its ancient name, is today visible on the council buildings.
In 1798 the French troops who had invaded the Papal States plundered the town after the people had displayed stubborn but futile resistance. By decree of Vittorio Emanuele II in 1861, Massaccio regained its ancient name of Cupramontana.
Distance: km 15
Time advised: an hour and a half
From Piazza Kennedy (Kennedy Square) follow via Trieste (Trieste Street) for about a kilometre and after the third “stop” turn left towards the Vecchia Fornace (Old brick factory).
Take the gravel road alongside the fishing lake until you reach the tarmac road; then turn left and shortly after turn left again onto the white road that leads you back to town.
Turn right and join the S.S. 76; turn left and then right taking the road that leads to the motorway.
Having crossed the level-crossing and the bridge over the River Esino, proceed along the road for about 3 km; then turn left and climb up to Maiolati Spontini.
When you join the village, turn to the left for Colle Celeste.From here go back to the tree-lined avenue and turn right towards the descent.At the junction turn left and join the long descent called Boccolina.
Once crossed the bridge over the River Esino, turn right towards the Vecchio Rotone.
Then turn left and follow the road on the left crossing a small bridge. Go through the railway subway and join the S.S. 76 again. Turn left and you are easily back to Piazza Kennedy.