Amy McPherson
This is the second part of our two part series on epic Italian Gran Fondos. You can see part one, from last week, here.
Marcialonga Cycling
The region of Trentino is home to the quieter side of the Italian Dolomites and this beautiful Gran Fondo.
You’ll start and finish up in the spectacular town of Predazzo, that was one of the venues for the recently finished Milano Cortina Winter Olympics and the route will not just be challenging, it will also be beautiful.
Featuring four major Dolomiti passes: Costalunga, Pampeago, San Pellegrino and Valles, with a combined elevation gain of 3900 metres, with plenty of technical descends to get your heart pumping.
In May, the wild Alpine flowers fill the meadows with colour and the air with sweet fresh scent, a picture perfect backdrop for the picture perfect ride.
This year’s edition is on 31 May 2026. In 2027, the event will be held on 30 May 2027, and will be celebrating its 20th anniversary.
www.marcialonga.it/marcialonga_cycling
Gran Fondo Milano-Sanremo
The one where Tadej Pogačar recovered from a mid-race crash to a thrilling win with a photo finish sprint with Tom Pidcock on the Via Roma this year. Milano-Sanremo is as exciting as it sounds, and with Gran Fondo Milano-Sanremo, you get to race on the exact route of the professional “Classicissima”.
Don’t take participation lightly though, this is the longest Gran Fondo in Italy and one of the longest one day amatuer event globally.
Starting from Milan, the route is identical to the professional race that takes you on the two short climbs of Cipressa and Poggio before rolling across the finish line at Via Roma in Sanremo on the Ligurian Riviera.
This year’s Gran Fondo Milano-Sanremo will be held on 7 June 2026.
Granfondo La Fausto Coppi
Personally tried and tested by the writer, Granfondo La Fausto Coppi is considered as one of the most friendly races in Italy. Named after Italy’s Il Campionissimo, Fausto Coppi, who raced these same Alpine climbs during his dominance in the 1940s and 50s.
Have been held since 1987, this Gran Fondo is based in the town of Cuneo in the Piedmonte region and tackles a route that attacks the legendary Colle Fauniera, a 22.3 kilometre climb of 2481 metres, where you can quite literally see the end of the tree-line and come face to face with the exposed silvery granite peaks of the mountain.
The spectators are mostly residents who live in the region, whose enthusiasm mellows out the pain in your legs. Every wave and water squirt is fuel to keep going, and don’t forget a selfie with the statue of Il Campionissimo at the top before the scary descent down to earth.
This year’s edition will be held on 28 June 2026.
Maratona Dles Dolomites
Come get the hottest race ticket in town. A high profile Gran Fondo event, the Maratona dles Dolomites limits the number of registrations to ensure a split of 50% Italian and 50% international riders for fair play and to avoid overcrowding the mountains.
Held in the popular Alta Badia region of the Dolomites, the views and the whopping 4230 metres of climbing will both take your breath away. The race starts and ends in Corvara, and takes the riders into the passes of Campolongo, Gardena, Pordoi, Sella, Giau and Falzarego.
This year’s theme is ‘Pax, Peace’, to promote an international collaboration to achieving peace between countries. A key new feature this year will be an increased focus on female participation.
This year’s event will be held on 5 July 2026. In 2027, Maratona dles Dolomites will be celebrating its 40th anniversary.
Mila Marche
Marche is a small region wedged between Emilia-Romagna to the north and Abruzzo to the south, most famously known for its dramatic coastline is backdrop to the Sibillini Mountains.
The 5Mila Marche is a relatively new Gran Fondo on the scene, which begins from the seaside town of Porto Recanati, on the Adriatic coast which will give you a good overview of this less visited region of Italy.
Former Italian professional cyclist Andrea Tonti founded the event in tribute to his home region. He wants those who come race the 5-Mila for a weekend that combines cycling, local culture, food among the vibrant race atmosphere at the event village where participants can taste the local cuisine of the Marche region.
Next race is held on the weekend of 18-20 September 2026.
What about something a little longer?
Bikepacking events are on the rise and there are no better place organised than in Italy, where plenty of bike trails can be used to plan an epic itinerary.
Those looking to be part of a even community can consider the two recommended below where there are no definitive schedule, no gun start, no podium. Just the pure joy of cycling.
Milano Cortina Great Ride
A new bikepacking event to celebrate the 2026 Milano-Cortina Winter Olympics and Paralympics, the Milano Cortina Great Ride is back for its second edition this September following a successful debut event last year.
A bikepacking event that connects the two host cities of the Winter Olympics follows a route of mixed asphalt and gravel through some of the country’s most spectacular landscapes.
Across 500+kilometres, the journey will travel across eight provinces from the city of Milan to the shore of Lake Garda, then eastwards towards the romantic city of Verona, through Treviso and the prosecco landscape of Valdobbiadene, pass through several UNESCO World Heritage Sites along the way to finish in Cortina d’Ampezzo in the Dolomites.
The 2026 event is scheduled for September. Exact dates TBC.
Tuscany Trail
Founded in 2013, Tuscany Trail is the world’s largest gravel bikepacking event with over 6,100 participants from more than 74 countries.
Think vineyards and olive groves and scatters of farmhouses among the vast Tuscan landscapes, from the city of Siena to the skyline towers of San Gimignano, to the rolling green hills of Val d’Orcia, the gravel white roads of strade bianche and the wild Tuscan coastline. This is 445 kilometres of great bikepacking that will show you Tuscany at its rawest and authentic.
Along the route, Base Camps arranged by local organisations provide free or low-cost rest points where riders pitch tents, share meals, and connect with the local community.
Tuscany Trail 2026 takes place May 20–26, starting and finishing in Campiglia Marittima.
This year’s event has been sold out. Details of the 2027 event TBC.
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Amy McPherson
Amy McPherson - A London-based Aussie, Amy is a keen cyclist and runner. A highly-respected travel writer, she specialises in active travel in France and Italy.
