The Helldogs Take on the Alps

When we met Tes in the shop last year, we could tell he was serious about cycling. He took the Oltre Pro out for several days of big mountain rides and quickly recognized the potential for something much larger in our region. So when he reached out months later to plan an epic trip for his Sydney-based club, The Helldogs, we were thrilled.

Their goal? Nothing less than the iconic Stelvio, Gavia, and Mortirolo climbs in the High Alps, followed by a series of bold rides around Lake Como. With a shared appetite for adventure, Tes and Luca worked together to design a journey that would begin in Bormio, conquer the “Big Three,” and wind its way down to Bellagio for a few unforgettable days—before finishing with a ride straight into the heart of Milan.

The Helldogs arrived in full force—powerful, enthusiastic, and united by a camaraderie that was evident from day one. They were awed, humbled, and ultimately triumphant on the legendary Alpine ascents. The transition from Bormio to Lake Como, mostly on cycle paths, brought pure joy and a change of pace. In Bellagio, the history and challenge of the Ghisallo-Sormano loop left its mark, while the border crossing into Lugano offered some of the most scenic and varied terrain of the entire trip with a return to Lake Como entirely on bike paths and secondary roads. The final chapter? A bold ride through Valsassina, tracing the first half of Stage 18 from this year’s Giro d’Italia, before a triumphant arrival in front of the Duomo in Milan. Nearly 700 kilometers and over 10,000 meters of climbing—an unforgettable adventure shared with our guides Luca and Alberto.