4.3
(74)
1,919
riders
24
rides
Road cycling around Pennabilli offers diverse landscapes within Italy's upper Marecchia Valley, characterized by verdant hills and rugged terrain. The region features demanding climbs and scenic roads, providing a challenging environment for cyclists. Much of the area is part of the Sasso Simone and Simoncello Natural Park, contributing to the varied topography and panoramic views. This setting ensures a mix of physical challenge and natural beauty for road cyclists.
Last updated: July 12, 2026
4.6
(5)
107
riders
134km
07:15
2,690m
2,690m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.5
(2)
50
riders
63.4km
03:37
1,470m
1,470m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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5.0
(2)
35
riders
35.4km
02:23
1,100m
1,100m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
3.0
(1)
26
riders
39.3km
02:23
1,020m
1,020m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
22
riders
47.5km
02:51
1,210m
1,210m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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Worth visiting in October for the Truffle Fair
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Ivan Graziani Park in Novafeltria
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Marco Pantani pass, on Montefeltro a few steps away, view of the valley
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It is located on the Sasso del Lupo or Pietra Anellaria (from sandstone) and from the top of this natural cliff it dominates the underlying Savio valley. The fortress was probably built around the year 1000 by the Cavalca family of the Counts of Bertinoro, who at the time dominated the territory by ecclesiastical investiture. Around 1100 it was expanded by Altruda Frangipani, also of the Cavalca family, who managed the country with justice and wisdom ... When the Counts of Bertinoro died out ... the fortress belonged to the Archbishops of Ravenna and, later, to the Faggiolani, the Guidi, the Tarlati, the Brancaleoni, the Malatesta and the Montefeltro. And it was precisely with the arrival of this last family that the original fortress underwent the first radical transformations. ... it was the first change from a war bulwark to the princely residence that it would become with the Fregoso. .... In 1660 S. Agata and its castle returned under the dominion of the Church. Since then the fortress continued to be used as a residence at least until 1781 when it was transformed into a convent; on this occasion the Conventuals built, leaning against the fortress, the church dedicated to San Francesco della Rosa. Over the last two centuries the Fortress has been used as a Convent of the Friars Minor Conventual, a high school, a prison, a courthouse and finally a civilian residence. ... Today the Fortress is managed by the Pro-loco Association and is home to the permanent museum "Rocca delle Fiabe". (Source: https://www.roccadellefiabe.it/rocca-fregoso/ )
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In memory of Ivan Graziani, for all the dreams he gave us
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At an altitude of approximately 900 m above sea level on the right orographic side of the descent that goes from via maggio towards sansepolcro, from spring to autumn you often come across herds of grazing cattle that feed on the spontaneous herbs that the Apennines up there offer.
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Every time I pass by this road I photograph it, it is always different and above all its appearance and colour varies depending on the sky conditions and the presence of clouds.
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There are over 19 road cycling routes around Pennabilli, offering a variety of experiences for cyclists. Most of these routes are considered difficult, providing a significant challenge with substantial elevation gains.
Road cycling in Pennabilli features diverse landscapes within the upper Marecchia Valley, characterized by verdant hills and rugged terrain. You'll encounter demanding climbs and scenic roads, with much of the area falling within the Sasso Simone and Simoncello Natural Park. This ensures a mix of physical challenge and natural beauty, often with significant elevation changes.
While most road cycling routes in Pennabilli are rated as difficult due to significant elevation gains, there are a few moderate options available. For instance, routes like the View of Pennabilli Village – Passo Cantoniera di Carpegna loop from Pennabilli, though difficult, can be adapted for those looking for a challenge, but true beginner routes are limited in this mountainous region.
Pennabilli's road cycling routes offer stunning panoramic views of the Marecchia Valley and the Apennine landscape. You can pass by significant mountain passes like Bocca Trabaria, Viamaggio, and Passo Cantoniera di Carpegna. Additionally, you might encounter cultural landmarks such as the Hermitage of Saint Alberico or the San Leo Fortress and Historic Village, which offer historical insights and scenic stops.
The region is ideal for road cycling during spring and autumn when the weather is milder and the landscapes are particularly vibrant. Summer can also be suitable, though some climbs might be more challenging in higher temperatures. Winter cycling is possible but may be limited by snow and colder conditions, especially at higher elevations and mountain passes.
Yes, for experienced riders seeking a significant challenge, routes like the Alpe Della Luna – Passo Cantoniera di Carpegna loop from Maciano offer extensive distances and considerable elevation gains, stretching over 132 km with over 2600 meters of ascent. These routes are designed for very good fitness levels.
The area is highly rated by the komoot community, with an average score of 4.06 stars from more than 10 reviews. Cyclists often praise the challenging mountain passes, the stunning panoramic views of the Marecchia Valley, and the diverse terrain that provides both physical challenge and natural beauty.
While specific cafes on every route are not detailed, Pennabilli and its surrounding medieval villages offer opportunities for refreshments. The town itself has amenities, and some hotels in the region are bike-friendly, potentially offering services for cyclists. Planning your route to pass through villages is recommended for stops.
Pennabilli is situated in a more rural part of Italy's upper Marecchia Valley. While local bus services connect Pennabilli to larger towns, direct public transport options specifically for cyclists with bikes might be limited. Driving and parking in Pennabilli is often the most convenient way to access the cycling routes.
Pennabilli, as a town, offers various parking options. You can typically find parking in or near the town center, which serves as a common starting point for many routes. For specific routes, checking the komoot tour details for suggested starting points and parking information is advisable.
Yes, many of the road cycling routes around Pennabilli are designed as loops, allowing you to start and end in the same location. Examples include the View of Pennabilli Village – Passo Cantoniera di Carpegna loop from Maciano and the Marco Pantani Pass – Passo Cantoniera di Carpegna loop from Pennabilli, which offer comprehensive tours of the region's highlights.
The Sasso Simone and Simoncello Natural Park covers a significant portion of Pennabilli's territory, meaning many routes traverse this protected area. Cyclists will experience lush Apennine landscapes, diverse flora and fauna, and stunning panoramic views of the Marecchia Valley. The challenging climbs often lead to rewarding vistas over these natural features.


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