Amandola's name apparently derives from the beautiful Fillide who, according to mythological history, whilst desperately searching or her love, arrives in Amandola. As she can not find him anywhere, she believes he is dead and sadly kills herself. It is said the Gods then transformed her mortal body into an almond tree. From this comes the name "Amandola". (almond = mandorlo!).

The layout of the area comes from the strategic positions of the various human settlements throughout the centuries: from the Piceni to the Romans, the Longobard invasion to the Benedictine and Farfense monks. The municipality is formed by the linking of three hills, parts of which are still visible in the form of the historical town centre. These three hills were called: Marrubione, Castel Leone and Angelo. As the area developed, Castel Leone became the core of the town and its role was maintained until Amandola was surrounded by walls. The square is dominated by the Podestà Tower which, together with several other buildings, makes up the complex of the Municipal Theatre. Built in the late 17th century, the theatre is a great example of the architecture of the time. It’s present aspect is due to a restoration project the following century.

In the 18th century, the town had a population of 2,000 inhabitants. Between the 18th and 19th centuries, the town gradually changed from wooden houses, which were easily inflammable, to brick. An interesting story is to be found in the name of the theatre: la Fenice (the Phoenix). It shows how the new theatre rises from the ashes of the old one. It now seats 120 and the horseshoe structure and the decorations make the theatre a fascinating reason to visit.

Going down from the square, it is possible to see various Renaissance buildings from the 17th century. At the end of the road, directly in front is the complex of St Francesco. Its facade has a beautiful 13th-14th centuries portal - on its arch there are carved dragons. Of remarkable beauty are the frescoes in the bell tower and the wooden crucifix. The recently restored convent, now holds the Anthropological and Geographic Museum and the cloister houses the Museum of Rural Life, the History Archive and the Municipal Library.

Passing down towards the present town centre, we arrive at the square of the Collegiate Church, recently restored and used as municipal offices. Along the old main street, we reach the Risorgimento square, the old Vallelunga square, which is dominated by the Church of the Beato Antonio, with annexed convent, founded in the middle of the 15th century. Its Baroque facade features some niches where, probably, once were the statues of the saints. Inside the church are the mortal remains of the Beato Antonio. The building to the right of the Church with portico houses the Town Hall.

The present layout of the square dates back to the end of the 19th century, when the roads linking Ascoli to Macerata and Amandola to Fermo were being built. At that time the square was the main passing route to reach the railway station where, on December the 14th 1908, it was officially inaugurated. The railway brought many economic advantages, but it was closed in August 1956. Today the square is once again the centre of public life. From here you can climb up the Colle Marrubione, on the top of which is the Capuchin convent.

Leaving the town, on the road leading to Comunanza, as you turn down towards the river Tenna, there is a lovely water-mill (sadly no longer in use). Of interest are its walls which look like those of a fortress. Just past here is the famous Romanesque bridge which features a single archway At a fork in the road before the Romanesque bridge, the old railway line and the ancient path towards the Abbey of St Ruffino leads off; but unfortunately, it is no longer traceable. The Abbey is difficult to date but the building is probably erected on a pre-existent Romanesque base. The crypt houses the mortal remains of Saint Ruffino.

In the 15th century, Amandola had a surface area of 10 km² and a population of 14,000 industrious inhabitants. They produced leather, wool, hats and agricultural goods. Amazingly enough there were 108 churches, plus numerous monasteries and convents.

Also of interest is also the Church of St Tommaso, positioned along the old main street, which is now used as home for senior citizens. Now Amandola has a population of 4000 inhabitants and is positioned at 550 m above sea level, on a hilltop dominating the valley of the Tenna river. The surface area has grown to 69.42 km²; occuping the north-western part of the province of Ascoli Piceno, and borders to the province of Macerata. Due to the interesting location and history over the centuries, the town of Amandola represents a natural base from which to explore the vast stunning area of the Sibillini Mountains.