What is the longest one-day road cycling race?

Milan–San Remo is the longest one-day road cycling race.

Usually held in March, the Italian Classic covers about 298 kilometres between Milan and Sanremo on the Ligurian coast. Its extraordinary distance has earned it the nickname “La Classicissima,” and it is one of cycling’s five Monuments.

The race began in 1907 and is traditionally the first Monument of the season. Although the route is extremely long, it is not dominated by one massive mountain. Instead, the decisive finale features the Cipressa and the Poggio, whose short, late climbs can distance pure sprinters before the descent into Sanremo.

A common mix-up is Paris–Roubaix, which is more famous for its brutal cobbles but is shorter. Milan–San Remo’s challenge is sustained endurance: riders must survive nearly 300 kilometres and still have the strength to attack or sprint at the finish.