Pro cycling is packed with references to its history and tradition, but racing has changed a lot since the early days. What we see today is a far cry from the first races in the late 19th century, but several big events have gone the distance and are still prominent features of the pro calendar.
So we’ve popped into the time machine to see how cycling’s five longest-running races have changed since their first editions, plus what became of some of the other races from that era.
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5. Giro di Lombardia (1905)

Like many cycling races, Il Lombardia was the brainchild of a journalist. This time it was the young editor-in-chief of Italian newspaper La Gazzetta dello Sports, Tullo Morgagni, who would also go on to create the Giro d’Italia and Milan-San Remo.
First run as Milano-Milano on 12th November 1905, it was set up by Morgagni as a ‘rematch’ between Pierino Albini and Giovanni Cuniolo, who had previously faced off in the Coppa del Re. Just 54 riders started the first edition of the race, which was 230km long and went from Milan via Bergamo and Como back to Milan. It was Giovanni Gerbi who reigned victorious that day by more than 40 minutes ahead of compatriots Giovanni Rossignoli and Luigi Ganna, the latter who would go on to win the first Giro d’Italia and the first Milan-San Remo.
The race’s name was changed to Giro di Lombardia in 1907, which held until 2012 when it became simply Il Lombardia. These days the race doesn’t bother with Milan, instead swapping between starting and finishing at Bergamo and Como, and packing in the climbing in between, with 4,735m of elevation these days compared to just 1,296m in 1905.
The same age as: The two-speed rear-wheel derailleur (invented by Paul de Vivie)
- Read more: The legend of the first Il Lombardia in 1905

4. Tour de France (1903)

The first running of the Tour de France looked a bit different to the one we know and love. Created by French newspaper L’Auto, the 1903 edition featured six stages for the peloton to ride from 1st to 19th July.
Yes, they had just six stages but the race ran over two weeks. That's because the length of the stages put each one into what these days would be ultracycling territory, with riders setting off before dawn and riding all day and into the night, and not all of it on the silky-smooth tarmac like the modern day Tour either. As a result, they had a rest day between each stage – compared to only two or three across three weeks in modern Tours – to make things more doable.
Stage 1 of the 1903 edition took riders from Paris to Lyon over a whopping 467km; Stage 2 then went from Lyon to Marseille over 374km; Stage 3 was from Marseille to Toulouse over 423km; Stage 4 was the shortest of the lot at 'just' 268km from Toulouse to Bordeaux; Stage 5 headed from Bordeaux to Nantes over 425km; and the final stage was 471km from Nantes back to Paris. There were no transitions between stages and so it was a true tour.
The yellow jersey for the overall leader wasn’t introduced until 1919 – back in 1903, a green armband signified the race leader. Chimney sweep Maurice Garin would be the first winner, his final advantage almost three hours over second place Lucien Pothier, and he won 6,075 francs for his efforts. Obviously the nature of the race in those early days had a lot to do with it, but that gap of 2h 49min 21sec remains the biggest ever winning margin in Tour de France history.
To put that into modern context, that's about the time difference between 2024 Tour winner Tadej Pogačar and Geraint Thomas all the way down in 42nd place, who finished 2h 47min 36sec down. Sorry Geraint.
- The same age as: The aeroplane (Wright brothers’ Wright Flyer)
3. Paris-Roubaix (1896)

Two Roubaix textile manufacturers are to thank for the existence of Paris-Roubaix. The pair, Théodore Vienne and Maurice Perez, had built a velodrome in 1895 and began to attract the world's best track riders. To try to bring more attention to Roubaix, a small mining town, and the velodrome itself, they decided they wanted to run a race from Paris to the velodrome.
Initially pitching it as a warm-up to the much longer Bordeaux–Paris race (more on that later) that came a few weeks later, they called on the editor of Le Vélo, Louis Minart, for help. Minart sent Victor Breyer (who would go on to help organise the Tour de France and was actually born in Southwold in Suffolk) to find a route, but his journey was so brutal that he considered dropping the whole thing altogether.
The first edition took place on 1896 and was won by Josef Fischer after 280km, who remained the only German to have won Paris-Roubaix until John Degenkolb in 2015. The race truly began to grow its legacy after World War I, with bombing and fighting having devastated the region, laying waste to much of the terrain that future editions would cover.
While in the race's early days riders rode over cobbles simply because that was the state of the roads at the time, in modern times the cobbled secteurs are what makes Paris-Roubaix special, and those stretches of pavé are maintained by Amis de Paris–Roubaix, a non-profit group of volunteers. In order to make the most of the cobbles while maintaining a similar overall distance – just under 260km in 2024 – to early runnings of the race, today's Paris-Roubaix starts in Compiègne, about 100km northeast of Paris.
- The same age as: A patent for a mechanical self-tipping hat (James C. Boyle)
2. Liège-Bastogne-Liège (1892)

Dubbed ‘Le Doyenne’, meaning ‘The Old Lady’, Liège-Bastogne-Liège has been running since 1892 and is the oldest of the Monuments. It was created by L’Express, a French-Belgian newspaper, and the first edition ran from Spa to Bastogne and back over 250km of racing.
All 33 amateurs who entered were Belgian and came from either the Pesant Club Liégois or the Liège cycling union. With the turning point of the course handily being the Bastogne train station – a fair few riders abandoned here and headed back to Spa. Liège’s Léon Houa was the first victor after soloing away prior to the first climb of the Cote de Aywaille, and he was able to pass his rivals who were still heading towards the train station as he was on the return leg. He eventually clocked a time of 10h 48min, beating the second placed rider by 22 minutes.
After Houa took three consecutive victories, the race took a hiatus for 14 years. Upon its return, the start and finish points were moved to Liège and thus Liège-Bastogne-Liège as we know it was born. These days the race is about the same length overall – although tweaks have been made to the route over the years – but is finished far quicker, with last year's winner Pogačar taking just over six hours.
- The same age as: The American Psychological Association (G. Stanley Hall)
1. Milano-Torino (1876)

Milano-Torino doesn’t get the respect it deserves for being the oldest Classic in cycling, probably because it's not one of the 'Monuments'.
The first edition of Milano-Torino was held in 1876. Only eight riders lined up at the start and they were riding a precursor to the modern bicycle with much bigger wheels. The eventual winner – by more than an hour – was 21-year-old Paolo Magretti, who was studying zoology at the time. The race only started to be held on an annual basis after 1913, which was only the eighth edition.
Compare the headline stats to the most recent running of Milano-Torino and it’s easy to see just how far the race, and cycling, have both come. The 2024 edition was won by Italian Alberto Bettiol, had 119 riders cross the finish line in Turin and only a 15-minute gap separated Bettiol from last-placed finisher Axel Zingle. It does still run from Milan to Turin, though.
- The same age as: The telephone (Alexander Graham Bell)
Honorary mentions
Giro del Piemonte (1906)
Just missing out on a place in the top five, the Giro del Piemonte was first run in 1906 in Alessandria, Italy, over 320km. Like quite a few races at this time it was won by Giovanni Gerbi, who would win in 1907 and 1908 too. He is one of five men to share the title of most victories, with Gino Bartali (1937, 1939, 1951) also among them.
It would take almost six decades for a non-Italian to win here, with Belgian Willy Bocklant beating Spaniard Jaime Alomar in 1964. The race still runs today under the name Gran Piemonte, with Neilson Powless the first American to win in 2024.
Bordeaux-Paris (1891)
Bordeaux-Paris was created in 1891 (a year before Liège-Bastogne-Liège) and averaged around 560km. Brit George Mills won the first edition as an invitee and covered the distance in 26h 36min 25sec. What set the race apart was that riders were paced behind motorised dernys for part of the overall distance.
Quite a few big names have won the race over the years, including Henri Pélissier in 1919, Tom Simpson in 1963 and Jacques Anquetil in 1965. But in the 1980s, interest began to wane and the last motor-paced edition was held in 1985. Three more editions ran from 1986-1988 with Jean-François Rault the last victor.
Bordeaux-Paris returned as a one-off in 2014 as a sportive and later in 2022 as an amateur event.
Paris-Brest-Paris (1891)
Paris-Brest-Paris was formed in 1891 and first won by Frenchman Charles Terront on a British-made Humber after 71 hours without sleep. Originally only open to 207 French riders, this long-distance event stretched over the 1,000km mark and ran from the Champs-Élysées in Paris to Brest and back.
A ten-year interval followed before the second edition, which took place in 1901 and was sponsored by Le Petit Journal and L'Auto-Velo. It separated professionals from the 'touriste-routier' group and France would reign victorious again with Maurice Garin clocking a time of 52 hours. This helped sell so many newspapers thanks to the telegraph system relaying results to the press that a bigger race – the Tour de France, which Garin also won – was concocted.
Paris-Brest-Paris has gone through many changes over the years. An audax was introduced in 1931, so cyclists would ride the course in groups of ten. It last ran as a 'professional' event in 1951 and has been an amateur ride ever since. Today it is one of the most – if not the most – most prestigious audaxes on the planet.
- Read more: Paris-Brest-Paris, the audaxers audax
