I was halfway up Italy’s Passo dello Stelvio, a 48-switchback beast in the Alps that’s widely regarded as one of cycling’s most mythic and punishing climbs, when the altitude kicked in. We were approaching 9,000 feet, after all. But rather than hurl my oatmeal breakfast, I settled into a manageable rhythm as the lead group of sinewy-legged climbers pedaled away from me.
Seasoned bike racers refer to this moment as getting dropped. But I hadn’t clipped in to win. The annual Dreilander Giro is a 104-mile, fully supported ride known as a gran fondo, and its main purpose is to challenge riders with dramatic terrain—vertiginous climbs, historic cobblestones—while also providing cushy comforts like aid stations, bathrooms, and a SAG wagon. Fondos are not like century rides: these are serious riders with high-end rigs. Still, they feel rewarding no matter where you place in the pack.