Fans, journalists, and racers distinguish Milano-Sanremo, De Ronde van Vlaanderen, Paris-Roubaix, Liège-Bastogne-Liège, and Il Lombardia from the sport’s other classic races, because of their scale, their grandeur, and their history.

Each of the Monuments is close to 250 kilometers in length. Besides the grand tours, they are the most anticipated, watched, and competitive bike races of the year. To win one would be a crowning achievement in any rider’s career.

In over a century of racing, only three riders have won all five of them: Rik Van Looy, Eddy Merckx, and Roger De Vlaeminck. That is because each of the Monuments pushes different aspects of a rider’s ability to their very limit. And there are no second chances. One false move can end a contender’s hopes of victory for another year. Riders will work for months to arrive on the start line of a Monument in their best form. Then, it all comes down to the day.

The next chapter in a hundred-and-more-year-old story is decided in a few hours of explosive action.

Milano-Sanremo is known in Italy as La Primavera, the spring classic. For over a century, this near-300-km-long classic has been a rite of spring. The long, flat journey south reaches its first apex when the race crosses the Turchino Pass and drops down to the Riviera dei Fiori on the Ligurian sea. It then builds to a crescendo over a series of short, steep climbs along the coast, culminating in the furious ascents of the Cipressa and the Poggio. As attackers launch off the front of the peloton, sprinters try to hold on and catch up on the white knuckle descents towards the finish line in Sanremo. Fortune favors the brave after close to six and a half hours of racing.

De Ronde van Vlaanderen is much more than a bike race. It is a national folk festival in Flemish-speaking Belgium. But what a bike race it is. Hundreds of thousands of fans trek out into the low hills and windswept fields of Flanders, gathering outside bars and in town squares to watch the peloton clatter over the concrete roads and cobbled farm tracks that crisscross the countryside. Dozens of short, steep climbs shape the race course. The peloton sprints towards each one of them, taking huge risks to hit the slopes first, so they won’t be stuck behind on the narrow roads if attacks start to go. By the end, only the strongest of the strong are left at the front of the race. Exhausted, they trade blows over the cobblestones until the winner is decided.

Paris-Roubaix is perhaps the most brutal bike race of them all. In France, they call it L’Enfer du Nord, the Hell of the North, a designation it first earned in 1919, when the race returned to the decimated region shortly after the end of the First World War. Although super highways and smooth country roads have since been built, Paris-Roubaix returns to the battered cobblestone tractor tracks that have hardly been improved since every year to celebrate the enduring spirit of toughness and defiance that the local people hold dear. The first goal of every rider who starts Paris-Roubaix is to make it to the smooth banked curves of the cycle-racing track at the end. At times, it can seem like an all but impossible adventure. The roads that the race crosses are absurd, rocks jutting up this way and that, jackhammering riders from the ground. Nevertheless, they push on, in spite of their luck and the pain in their arms and their legs and their hands, until they make it to the final smooth lap or simply can’t. The winner is always a great champion.

Liége-Bastogne-Liége is the oldest Monument. Held in the wooded hills of the Belgian Ardennes, it is a climber’s classic with more meters of vertical ascent than the hardest grand tour mountain stages. The race swoops south from the faded industrial city of Liège to Bastogne, site of a famous WWII battle between American and German forces, before returning north. The climbs then come one after the other all the way along the homestretch. The most famous ones—the Stockeu, Haute-Levée, La Redoute, and the Côte de la Roche-aux-Faucons—are packed with thousands of fans. Everyone wants to see the decisive attack. When it comes, it often looks spectacular, but Liège-Bastogne-Liège is really a race of attrition. The course is so hard that by the end only the very strongest have any power left in their legs.

In Italy, they call Il Lombardia the Classica delle foglie morte, the race of the falling leaves. It is the most important of the fall classics. Raced in the hills around Lake Como, northeast of Milan, between Como and Bergamo, it is as brutal as it is beautiful. The most famous climb on the race course is the Madonna del Ghisallo, which starts by the lakeshore in Bellagio and rises to a church blessed by the Pope in 1949 to be the patroness of cyclists. Others include the Passo della Crocetta, Zambla Alta, and Passo di Ganda, which are each close to ten kilometers long. The peloton rarely takes on climbs of such length in a one-day race, which makes the effort all the more intense. Riders throw down all of their cards in hopes of grasping a last glimmer of glory before the season comes to an end.