This itinerary is a fascinating journey through the historic heart of Filottrano, a town that reveals its long history—from its Lombard origins to its architectural splendors and the painful memories of World War II.

The route ideally begins with a tribute to the legendary past of the town: the Statue of Ottrano in Piazza Mazzini. According to tradition, this figure was the Lombard founder of the castrum and provides the perfect introduction to the town’s history. Behind it stands the imposing Porta Nuova, the main gateway marking the entrance to the ancient 14th-century city walls.

Passing through the gate, you arrive at the vibrant Piazza Mazzini, the true beating heart of life in Filottrano. It is an elegant and welcoming square, known for its panoramic loggia that opens onto breathtaking views of the gentle Marche hills surrounding the town.

From here, the itinerary leaves the central Corso to enter Vicolo delle Mura Castellane. The journey takes on a medieval character here, leading to the remains of the fortifications. The most distinctive feature is the Octagonal Tower, a rare example of military architecture whose eight-sided plan reflects the defensive engineering of the era.

Returning to Corso del Popolo, the route continues to Piazza Garibaldi, where the Church of the Holy Stigmata is located. Its intentionally simple and austere façade hides a surprising and sumptuous interior, a celebration of Baroque decorations, frescoes, Corinthian capitals, and a fine wooden altar.

A little further on the right lies the Monastery and Church of Santa Chiara. Founded in 1578, it stands out for its reddish façade adorned with a statue of the Virgin. History is still alive here: the Clarisse Monastery remains active, devoted to a cloistered monastic life.

Continuing through the alleys of the historic center, you reach the Church of San Francesco (1531), another gem that deserves a contemplative pause.

Next to San Francesco rises the seat of civic power: the Palazzo del Comune. This fine Renaissance building (1530) is flanked by the slender Civic Tower, recognizable by its clock and evocative battlements, symbolizing the town’s identity.

Descending toward Porta Marina, you encounter the majestic Church of Santa Maria Assunta (1679). Fully Baroque, it is a small treasure chest of art, housing important paintings by artists such as Parrocel and Van Schayck. Here, with due respect, rest the remains of Giacomo Costantino Beltrami, the famous Filottrano-born explorer and patriot.

The walk concludes in a place of rest and remembrance. Accessible via a scenic white staircase, the Public Gardens offer a splendid panoramic area, perfect for a restorative pause next to the Monument to the Fallen.

A little beyond the gardens stands the millennial Church of San Cristoforo, founded in 1218 by the monks of Fonte Avellana. Its architecture, a fascinating blend of Romanesque and Gothic elements, houses inside a valuable cycle of frescoes, including The Last Supper, the Baptism, and the Nativity.

Finally, for those wishing to delve into more recent history, the Permanent World War II Exhibition (often reachable with a short drive) and the Filottrano Battle Memorial (July 1944) offer a moving tribute to the memory of one of the bloodiest clashes on the Adriatic front.