The village has Roman origins and was fortified in the middle Ages; it was also a place of residence for local seigniories. In 1259, during Manfredi’s occupation, the inhabitants rebelled and destroyed the stronghold on top of the mount. The Da Varano family, who had taken possession of the village and who would keep it until the 16th century, built the fortress in 1375. After that period the village returned under the Church State’s rule.

Penna San Giovanni is located on a hill dominating the valleys of streams Salino and Tennacola and is surrounded by a wide panorama, ranging from the Mount Conero to the Mount Maiella. Its origins are still mysterious, yet many findings allow scholars to date it back to the 1st – 2nd century A.C.

In the 12th century the village was known as Castel della Penna (perhaps due to a Celt etymology, the word Penna indicated a place on a steep height) or Castello di Monte San Giovanni (in honour of Blessed Giovanni who lived here). The hamlet still preserves its typical medieval aspect with the walls and the entrance doors, and owing to its strategic position the lords of nearby villages (families Bonifazi of Fermo, Da Varano and Sforza) disputed it.

Crossing the Gothic Porta Marina seems to go back in time, the most ancient part of the village, where the breeze from the sea mixes with the healthy breeze from the Mounts Sibillini, shows compact sandstone buildings. Set amidst these walls that watch over the coming and going of passers-by, the porte dei morti (doors of the dead), walled up forever, bear witness to the border between earthly life and eternity.

The Torre della Comunità has been watching over the inhabitants since 1100, whereas the 15th-century church San Francesco, rearranged in the 18th century, has kept for centuries the noble remains of the most famous citizens. The Town Hall hosts many ancient findings, as well as a triptych by Crivelli’s school. The church San Giovanni Battista preserves a 16th-century cedar-wood statue of Saint John the Baptist.

In the highest part of the hill, totally immersed in a unique landscape, the remains of the Fortress seem to be fighting against the strain of time.

Penna San Giovanni boasts a fruitful activity in the wool, brick and crockery sectors, and is also a busy spa, thanks to its Fonti di Aiello, springs whose waters contain bromine, sulphide and iodine.