Historical Route

The ancient walls of Monterubbiano date back to the 13th century, when they were fortified by order of Pope Honorius III as part of his defense plan for the towns of the Marche region against Saracen incursions. However, it was under the rule of the Sforza family—particularly between 1443 and 1446, during the time of Francesco Sforza—that the walls were strengthened and expanded, eventually reaching a length of approximately 2 kilometers.

Today, the wall is open at three main access points, corresponding to the historic gates: Porta del Pero, Porta Sant’Andrea, and Porta San Basso, also known as Porta Vecchia. In the past, the walls were also protected by four fortifications, now lost:

• Il Cassero, of which some traces remain in the foundation area outside Palazzo Secreti;
• The Pentagon Tower, the main lookout point;
• Il Girone, located between Porta del Pero and Porta Sant’Andrea;
• Rocca Coccaro, in the area now occupied by the public park of San Rocco.

Porta San Basso (or Porta Vecchia) is located at the southeast corner of the city walls, just above the steep slopes of the hill descending into the Aso river valley. Originally known as Porta Vecchia, it is, along with Porta del Pero, one of the city’s oldest entrances. The current name refers to Saint Basso of Nice, patron saint of Cupra Marittima, perhaps in memory of a nearby place of worship dedicated to him.

The defensive structures of the gate were likely built between the 13th and 14th centuries. The oldest visible part, based on its style and materials, can be dated to the 14th century. Just above the gate stood Il Cassero, a massive tower defending the citadel, whose remains can still be seen in the nearby Palazzo Secreti.

This fortified entrance witnessed numerous military events: from incursions by troops from Fermo, seeking to subdue Monterubbiano, to occupation by Rinaldo da Monteverde during his lordship. In the 15th century, it was contested by the forces of the Migliorati and the Malatesta, until Francesco Sforza’s arrival in 1433, a turning point that led to the renewal of the entire fortification system.

Gradually falling into disuse from the 17th century onward, the defensive structures remained in good condition until the 19th century, when they began to be abandoned. Today, Porta del Pero is among the best preserved, while other sections of the walls are in ruins.

Porta San Basso is accessible both from within the historic center and from the road branching off the provincial route near the rural church of Santa Maria del Soccorso. Visitors are greeted by a small opening topped with remnants of battlements, flanked by two towers: a larger one integrated into the walls and a smaller one angled toward the valley, where cannon holes used for firing bombards are still visible.

Just below the smaller tower begins the old road that once led to the valley, along which one can glimpse the ruins of the Church of the Madonna Celeste, built in the 17th century. Beyond the rivellino (an outer defensive work), one enters an open space leading to the main gate, built on a 14th-century tower now missing its upper part. The outer Gothic arch is finely crafted, with two frames, the innermost of which features sandstone inlays.

The large inner chamber opens toward the town, revealing the pillars that once supported the now-lost tower. The trace of the former upper level is still visible and has been converted into a small sloped-roof space. A small window opens at the center of the vaulted ceiling. Inside, a groove cut into the thick wall shows where the defensive grate (portcullis) would be lowered to block access if the main gate (of which the hinges remain) were breached.

Porta Sant’Andrea opens on the southern side of the city walls and takes its name from the now-lost church of the same name, some of whose sandstone remains may still be embedded in the defensive structures. Unlike the other gates, this entrance is not medieval in origin—it was opened only in 1765 for the visit of the Papal Legate, Cardinal Pio Emanuele di Savoia. For this reason, it has no association with military events.

The small arch, carved into the side of a now-ruined perimeter tower, overlooks a public park. The nearby sandstone structures may belong to the remains of the Church of Sant’Andrea. After passing through the gate, one walks along a quiet path that leads to the Strada del Girone, an area inside the western walls now largely unbuilt. From here, it’s possible to re-enter the heart of the historic center, emerging right in front of the Church of Saints Stephen and Vincent.