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Fortezza del Girifalco – Montecchio Vesponi Castle loop from Camucia-Cortona

Routes

Mountain biking trails

Fortezza del Girifalco – Montecchio Vesponi Castle loop from Camucia-Cortona

Hard

115

riders

Fortezza del Girifalco – Montecchio Vesponi Castle loop from Camucia-Cortona

05:20

60.9km

1,230m

Mountain biking

Hard mountain bike ride. Very good fitness required. Advanced riding skills necessary. Some portions of the route may require you to push your bike. The starting point of the route is accessible with public transport.

Last updated: June 26, 2026

Tips

Includes very steep uphill segments

You may need to push your bike.

After 20.2 km for 863 m

After 38.7 km for 138 m

Waypoints

Start point

Train Station

Get Directions

15.6 km

Church of San Cristoforo

Highlight • Religious Site

In this church, in the sacristy, in the priest's house and his perpetual house I grew up.
My uncle Don Antonio and his sister, Aunt Anna, lived there and I remember well the smell of incense mixed with that of summer.
I will always carry it with me.

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17.8 km

Fortezza del Girifalco

Highlight • Castle

Located at 651m above sea level, the Medicea or Girifalco fortress is located at the top of the hill overlooking Cortona (AR), a little higher than the basilica of Santa Margherita.

It was built in 1556 by Gabrio Serbelloni and Francesco Laparelli from Cortona at the behest of the Grand Duke of Tuscany Cosimo I de 'Medici. The fortress stands on the ruins of a previous one from the 12th century which was built on the remains of Etruscan walls.

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18.1 km

Historic Center of Cortona

Highlight • Settlement

The historic center of Cortona is simply beautiful.
Be careful because it is a city built on the side of a hill and consequently the difference in height between the lower part and the top is considerable!

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28.1 km

Ripa di Sopra Ruins and Viewpoint

Highlight • Historical Site

Fat tires only..it can get muddy and technical up here.

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38.8 km

Montecchio Vesponi Castle

Highlight • Castle

Montecchio Vesponi Castle dominates the Val di Chio from a hill over 360 meters above sea level. With its crenellated walls, towers, and an imposing 30-meter-high square tower, it is one of the best-preserved medieval castles in Tuscany and can be recognized from afar throughout the valley.

Contested for centuries by Arezzo and Florence for its strategic position on the road to Cortona, it became a Florentine stronghold after the Battle of Campaldino in 1289. In the 14th century, it was also home to the famous mercenary captain John Hawkwood.

Today, the castle comes back to life with guided tours, events, and reenactments that evoke the atmosphere of the Middle Ages.

Translated by Google •

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