The Five Monuments of Cycling: The Races That Define Every Season

/ 01

What makes a Monument

The five Monuments are the oldest and most prestigious one-day races in professional cycling. All five predate the Tour de France (the oldest, Liège-Bastogne-Liège, was first held in 1892; the Tour began in 1903). A Monument is the hardest one-day race to win — typically 250+ km, with terrain (cobbles, bergs, steep climbs) that filters the field to a specific type of rider.

Winning all five Monuments — the career 'Monument sweep' — has only been achieved by three riders in history: Eddy Merckx (19 Monument wins), Roger De Vlaeminck (11), and Rik Van Looy (8, the original 'Emperor of the Monuments'). In the modern era, Mathieu van der Poel, Tadej Pogačar, and Wout van Aert are the active riders with multiple Monuments; Pogačar has won three different Monuments (Flanders, Roubaix, Il Lombardia) and is a realistic threat to the sweep.

/ 02

Milan-San Remo — La Classicissima (March)

Milan-San Remo, 'La Classicissima,' is the longest professional race on the calendar — approximately 300 km from Milan to the Ligurian coast at San Remo. The route is almost entirely flat until the final 40 km, which feature two short climbs: the Cipressa and the famous Poggio di San Remo. A descent from the Poggio leads to the flat finish on the San Remo seafront.

Milan-San Remo is known as 'the sprinter's Classic' because the climbs are gentle enough for a strong sprinter to survive. The race typically ends in a bunch sprint — but the attacking riders who go over the Poggio hard can sometimes stay away. The winner is either a sprinter who survives the climbs (Mathieu van der Puul, Jasper Philipsen) or an attacker who distances the sprinters on the descent (Pogačar won in 2025).

Established 1907. Most wins: Eddy Merckx (7). Recent winners: Van der Poel, Pogačar, Mohorič.

/ 03

Tour of Flanders — De Ronde (April)

The Tour of Flanders ('De Ronde') is the cobbled Classic of Flanders, approximately 260 km with around 20 short, steep cobbled climbs (the 'bergen') — the Oude Kwaremont, the Paterberg, the Koppenberg among the most famous. The bergs are not long but they are steep, cobbled, and come in rapid succession in the final 80 km.

Flanders is the cobbled Monument that rewards the strongest rider in the peloton. The bergs filter the field relentlessly; by the final climb, only a handful of riders are left. The race is a national obsession in Belgium — Flanders stops for De Ronde. Mathieu van der Poel and Wout van Aert define the modern era of this race.

Established 1913. Most wins: Achille Buysse, Eric Leman, Fiorenzo Magni, Tom Boonen, Fabian Cancellara (3 each). Recent winners: Van der Poel (multiple), Pedersen.

/ 04

Paris-Roubaix — L'Enfer du Nord (April)

Paris-Roubaix, 'L'Enfer du Nord' (the Hell of the North), is the most brutal one-day race in cycling. Approximately 260 km from northern France to the Roubaix velodrome, with around 55 km of pavé — ancient cobblestone sectors rated from 1 (hardest) to 5 stars. The Trouée d'Arenberg (the Arenberg Trench), the Mons-en-Pévèle, and the Carrefour de l'Arbre are the five-star sectors that decide the race.

Paris-Roubaix is not won by pure climbers. It is won by powerful riders who can deliver huge watts on the cobbles, survive the relentless pounding (the cobbles shake the bike and the rider to pieces), and handle the bike on terrain that is barely rideable. The finish on the Roubaix velodrome is the most atmospheric finish line in cycling — the winner rides a lap of the track to take the famous cobblestone trophy.

Established 1896. Most wins: Roger De Vlaeminck, Tom Boonen (4 each). Recent winners: Van der Poel (multiple), Pogačar.

/ 05

Liège-Bastogne-Liège — La Doyenne (April)

Liège-Bastogne-Liège, 'La Doyenne' (the oldest), is the Ardennes Classic — the climber's Monument. Established in 1892, it is the oldest of the five Monuments. The route covers around 260 km through the Belgian Ardennes, with 10+ categorized climbs. The defining triple of the final 40 km is La Redoute, the Roche-aux-Faucons, and the Côte de Saint-Nicolas.

Unlike the cobbled Monuments, Liège-Bastogne-Liège is a climbing race. The Ardennes climbs are not long but they are steep and relentless, and the strongest climber almost always wins. The race is the climax of the Ardennes week (following the Amstel Gold Race and La Flèche Wallonne). Tadej Pogačar, Remco Evenepoel, and Primož Roglič are the modern era's defining riders here.

Established 1892. Most wins: Eddy Merckx (5). Recent winners: Pogačar, Evenepoel (multiple), Roglič.

/ 06

Il Lombardia — La Classica delle Foglie Morte (October)

Il Lombardia, 'La Classica delle Foglie Morte' (the Race of the Falling Leaves), is the season-closing Monument, held in early October in the Italian autumn. The route covers around 250 km around Lake Como, with the Madonna del Ghisallo climb (the chapel dedicated to the patron saint of cyclists, containing a cycling museum) and the brutal Muro di Sormano ('the wall' — 2 km at an average of 17%, with pitches of 25%) as the defining features.

Il Lombardia rewards a climber who can sustain form late in the season, when most of the peloton is exhausted from the grand tours. It is the last major race of the year, and winning it caps a season with a Monument. Tadej Pogačar has made the race his own — multiple wins, often solo.

Established 1905. Most wins: Fausto Coppi (5). Recent winners: Pogačar (multiple, including 2021-2024), Evenepoel.

/ 07

Monument winners — all-time and current