The Milan–San Remo is on this Saturday, March 21st, and it is one of the most beloved one day races of the year. Let’s take a wee look at its history!

The Italian race is the longest race in professional cycling and one of the sport’s five Monuments. First held in 1907, the race stretches nearly 300 km from Milan to the Ligurian coast at San Remo, earning the nickname La Classicissima.

The inaugural edition was won by Lucien Petit-Breton, who braved brutal weather and primitive roads. Early editions were chaotic — riders often navigated muddy tracks, freezing conditions (just ask Eugene Christophe), mechanical failures they had to go full DIY on, and even ‘curious’ crowds who sometimes blocked the road.

Petit-Breton’s victory took over 11 hours, highlighting the brutal nature of early cycling. The success of that first edition convinced organisers the race had a future—and it quickly grew into cycling’s longest and one of its most prestigious one-day races.

Is it Petit-Breton…? Or Timothee Chalamet?!

The race’s legend grew thanks partly to daring attacks. In 1946, Italian hero Fausto Coppi launched a jaw-dropping solo attack with 150 km remaining, finishing nearly 15 minutes ahead of his rivals. It remains one of cycling’s most famous long-range victories. – and possibly the coolest…

Coppi was leading by 8 minutes. He slowed down at a cafe and got off his bike. Gingerly placing his bike against a railing, he walked in, ordered an espresso, drank up, paid and left. He went on to win the Milan to Sanremo stage with 14 minutes between him and the group. The feat was so impressive, that the radio commentator announced: “First, Fausto Coppi, whilst we wait for the second, we’re going to play some nice music”!

The modern race is defined by late climbs like the Poggio di San Remo and the Cipressa, where the final selection is often made before a frantic descent into San Remo.

Sprinters and attackers alike have triumphed. Eddy Merckx holds the record with seven victories, while modern stars such as Peter Sagan and Mathieu van der Poel have added explosive chapters to the race’s rich history.

More than a century later, Milan–San Remo remains cycling’s ultimate test of endurance, tactics, and perfectly timed attacks.