A Gran Fondo (loosely translated from Italian as ‘Big Ride’) is a mass participation cycling event on a scenic course attracting several thousand cyclists, ranging from (semi-) professionals to beginners. The characteristics of a Grand Fondo include individual achievements, camaraderie among riders, and winning prizes; hence, a combination of a race and a social event. A Gran Fondo provides excellent support for all cyclists, including infrastructure, mechanical support, safety precaution, food, and refreshments. For me, a Grand Fondo is always a big rolling party! In the following, I will describe several rides of my scientific career and conclude with lessons learned and some inspiring remarks.