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I heard recently that Simon Gerrans of the new Green Edge cycling team had won one of the monuments. What are these races?

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In the world of professional cycling, the 'Monument' races are five of the oldest and widely considered most prestigious one-day races held each year. They are:

  • Milan – San Remo (Italy)
  • Tour of Flanders (Belgium)
  • Paris–Roubaix (France)
  • Liège–Bastogne–Liège (Belgium)
  • Giro di Lombardia (Italy)

More information can be found on each race, and the "Classics" in general in the Wikipedia article Classic Cycle Races.

A key factor in the argument that Eddy Merckx is the greatest competitive cyclist ever is that he won 19 Monuments - the next rider on the list won 11.

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Upvote for Eddy Merckx reference just read his wiki somewhat of a God on the saddle –  will Mar 28 '12 at 16:17
    
Thanks for the +1. Most of us of the 7-11 team generation and older have no doubt - Merckx is, was and will forever be the one and only true God of cycling. I'm still shocked when I encounter a cyclist in full kit who when I mention Merckx thinks I mean Axel, or that I've mispronounced the pharmaceutical company. –  Gary.Ray Mar 28 '12 at 18:45
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From Peloton Magazine (http://pelotonmagazine.com/Wisdom/content/19/1112/Pro-Racing-The-Basics):

The Monuments Five races—Milan-San Remo, the Tour of Flanders, Paris-Roubaix, Liege-Bastogne-Liege, and the Tour of Lombardy—carry the distinction of being called the Monuments. They are so named because they began prior to World War I; the youngest of the events, the Tour of Flanders, was first run in 1913. The roads they travel were used during the World Wars and now the courses are lined with memorials to the war dead.

Milan-San Remo: At 298 km (185 miles), Milan-San Remo is the longest of the five Monuments. Traditionally run the third week of March, Milan-San Remo signals the shift into high gear for the Spring Classics. The race is held in Italy and its course runs from the city of Milan to the small town of San Remo on the Ligurian coast near the French border. Conditions are generally cold at the start but with the run to the coast, the finish is much warmer. The course features several significant climbs and the final two, the Cipressa and Poggio, are effective at thinning the pack so that only the strongest sprint for the finish. Italians have won the race in 50 of the 99 editions. Belgian Eddy Merckx holds the record for the most wins with seven.

Tour of Flanders: The Ronde van Vlaanderen is the first of the Northern Classics. It is generally run the first Sunday in April, one week before Paris-Roubaix. It covers a 262 km (163-mile) course from Brugges in the north to Ninove outside of Brussels. It is famous for its 17 hills, which range in length from 375 meters (410 yards) to 2.2 km (1.4 miles). The climbs are called “muur” (wall) because many are steep at some point; 11 of the hills have sections with gradients of 11 percent or more and eight have sections made up of cobblestone. If the roads are damp, riders are frequently forced to dismount their bikes on the steepest sections of hills and walk up. It’s a bit like trying to climb a mountain in your dancing shoes. Many Belgian riders have said that winning Flanders is more important to a Belgian than wearing the yellow jersey of the Tour de France. Belgians have won the race 65 of the 92 times it has been run. Achiel Buysse, Fiorenzo Magni, Eric Leman, and Johan Museeuw are tied for the record of most wins, with three apiece; all are Belgians except for Magni, an Italian.

Paris-Roubaix: Considered the “Queen of the Classics,” Paris-Roubaix is the only Monument run in France. Best known as the “Hell of the North” for the sections of cobblestone roads it traverses in Northern France, it is held the second Sunday in April.

Over its 260 km (162-mile) course, Paris-Roubaix submits riders to 28 sections of pavé (French for cobblestone). The sections of pavé range in length; some are as short as 200 meters (218 yards), while the longest are 3.7 km (2.3 miles). The sections are rated in difficulty from one star (easy) to five stars (reserved for the most difficult sections). These are the same cobblestone roads used in World War I. The most famous (and difficult) sections—the Arenberg Forest, Mons-en-Pevele, and Carrefour de l’Arbre—are traditionally the site of attacks that can tear the race apart. The cobblestones jar the body terribly, can be slippery, and are the source of untold numbers of punctures. Riders will run exceptionally low tire pressure (sometimes as low as 50 psi) in an effort to cushion them from the rough surface and reduce the likelihood of a puncture. Most don’t finish the race due to one or another of the many setbacks a rider can encounter. As a result, riders speak of the luck required to win at the velodrome in Roubaix. Crashes are frequent and often spectacular; it’s kind of a full-contact roulette.

The day’s weather can make a big difference in the race; if there’s rain, racers can be forced to ride through mud, while on dry days dust can affect racers’ breathing and vision. Imagine trying to skateboard through a quarry and you’ll have the idea. Though the race is French, it is a particular favorite of the Belgians, who have won it 52 times in 106 runs. Roger De Vlaeminck holds the record for the most wins: four.

Liege-Bastogne-Liege: As the oldest of all the Classics—first held in 1892—Liege-Bastogne-Liege is called “La Doyenne” (a sign of respect, something like Grand Dame). It is one of two Classics held in the Ardennes region of Belgium (the other is Fleche-Wallonne) and is known for an exceptionally hilly course with 12 notable climbs. Liege-Bastogne-Liege is held the last Sunday in April over a 261 km (162-mile) course. The course only takes in two of the 12 climbs in the 105 km run from Liege to Bastogne on the trip south, but after leaving Bastogne, the riders are taken on a circuitous route over 10 of the 12 climbs. And while the race is called Liege-Bastogne-Liege, the race’s finish is in the town of Ans, which is a bit like having a race called Denver-Colorado Springs-Denver finish in Boulder. Belgians haven’t fared so well in their race since Eddy Merckx’s last of five wins (the record) in 1975. Since then, only four Belgians have given a salute in Ans.

Tour of Lombardy: The “Race of the Falling Leaves” is the only one of the Monuments held in the fall. The running of the Giro di Lombardia signals the end of the season for most top riders. Generally held the second or third week of October, the Tour of Lombardy was originally called Milan-Milan, the course has changed many times; today the start takes place in Varese and the 242 km (150-mile) race finishes in Como on Lake Bellagio. The race contains a number of significant climbs, with six of them notable for their length. The race’s most difficult challenge is the climb up to the historic chapel of the Madonna del Ghisallo, which holds bikes and memorabilia of many great former riders. The 8.6 km (5.3-mile) climb contains a maximum grade of 14 percent. The race is an overwhelming favorite of Italian racers, who have won 67 of 102 races. Fausto Coppi holds the record for the most wins: five.

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