4.4
(70)
1,793
riders
105
rides
Touring cycling routes around Riserva naturale del Sasso di Simone traverse a landscape characterized by distinctive limestone cliffs, including the flat-topped Sasso di Simone and Simoncello, and diverse forests. The region features extensive turkey oak woods and varied vegetation, providing a constantly changing backdrop for cyclists. Hilly and mountainous terrain, with Monte Carpegna as the highest summit, offers a range of cycling challenges. This area combines significant natural features with historical attractions, making it suitable for outdoor activities.
Last updated: June 2, 2026
5.0
(1)
19
riders
39.7km
02:52
840m
840m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
17
riders
36.1km
03:28
1,170m
1,170m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(1)
9
riders
40.6km
03:21
1,120m
1,120m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1.0
(1)
7
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.8
(5)
82
riders
20.5km
01:46
700m
700m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Riserva naturale del Sasso di Simone
209th hike | Pennabilli loop starting from Villa Maindi ═════════════ 👇 Here's the 4K video 👇 https://youtu.be/Szbrl2NGvlQ
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It's the first step that our parents took us since we were little. To go on the snow or in the summer to take a walk to Sasso Simone and Simoncello. Always green, fresh. Now I come there by bike and it's always a new discovery.
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Marco Pantani pass, on Montefeltro a few steps away, view of the valley
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Iconic climb dedicated to the memory of Marco Pantani, short and intense, often above 10%.
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Here there are pretty much all difficulties between 4a and 7a. The "Rock of Orlando" is approx. 15 m high and there is even a bell to ring at the top🔔.
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Super beautiful nature at Monte Canale.
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The Riserva naturale del Sasso di Simone offers over 100 touring cycling routes. The majority, 93 routes, are classified as difficult, while 11 are moderate. There are no easy routes specifically for touring cyclists in this area, indicating a landscape generally suited for those with good fitness.
The region is defined by its distinctive limestone cliffs, Sasso Simone and Monte Simoncello, which are prominent landmarks. You'll also cycle through extensive turkey oak woods, considered among the largest in Europe, and diverse forests. Higher elevations feature upland meadows that burst with wildflowers in late spring. The varied topography includes hills and low mountains, with Monte Carpegna being the highest summit, offering a constantly changing and picturesque backdrop.
Yes, the area is known for its challenging terrain. For instance, the Alley to Castel di Sopra – Viewpoint of Sasso di Simone loop from Petrella Massana is a difficult 47.7 km route with over 1,400 meters of elevation gain, leading through areas with prominent limestone cliffs and panoramic viewpoints. Another demanding option is the Rocca di Pietrarubbia – Ascent to Monte Carpegna loop from Carpegna, covering 55.2 km with nearly 1,700 meters of ascent.
The area is rich in history. You can explore the remnants of "Città del Sole" (City of the Sun), a fortified city that Cosimo I de' Medici attempted to build in the 16th century, including the Ruins of Sasso Simone Fortress. The region also has a history of pagan cults, medieval merchants, and pilgrims. The distinctive profile of the Sassi themselves has historically served as a crucial landmark.
Absolutely. The region is renowned for its exceptional vistas. The Alley to Castel di Sopra – Viewpoint of Sasso di Simone loop from Petrella Massana specifically highlights panoramic viewpoints. On clear days, views from Sasso di Simone can extend all the way to the Adriatic Sea. The Sella dei Sassi also offers evocative views for those traversing the region.
Late spring is particularly beautiful, as the upland meadows around Monte Carpegna transform into a vibrant carpet of orchids, crocuses, and buttercups. The diverse forests also provide a beautiful and constantly changing backdrop throughout the warmer months. Autumn offers different beauty with moss and mushroom scents. It's advisable to check for accessibility information, especially regarding the Military Range of Carpegna, which can have restrictions.
Yes, many of the touring cycling routes are designed as loops, allowing you to start and end in the same location. Examples include the Pennabilli – Pennabilli loop from Petrella Massana, a 39.6 km trail, and the Alley to Castel di Sopra – Passo della Spugna loop from Case Barboni, a difficult 36.1 km path with significant elevation gains.
The routes in Riserva naturale del Sasso di Simone are highly rated by the komoot community, with an average score of 4.4 stars from over 60 reviews. Cyclists often praise the diverse landscapes, the challenge of the hilly and mountainous terrain, and the stunning panoramic views, especially from the distinctive limestone cliffs.
Yes, the reserve is home to a rich variety of animal life. You might encounter wolves, foxes, deer, skunks, and various birds such as hawks, owls, and woodpeckers. The diverse forests and meadows provide habitats for these species, offering opportunities for wildlife spotting during your rides.
The Interregional Natural Park of Sasso Simone and Simoncello has visitor centers in towns like Pietrarubbia, Pennabilli, and Sestino. These centers often offer equipped areas, fauna museums, and environmental education facilities, which can serve as useful starting points or points of interest during your touring cycling adventures. There is also a Picnic Area with Tables and Barbecue available.
One iconic route for cyclists is the Marco Pantani Pass – Ascent to Monte Carpegna loop from Carpegna. This 20.5 km route with over 700 meters of elevation gain is a tribute to the legendary cyclist Marco Pantani and offers a challenging climb to Monte Carpegna, the highest summit in the area.


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