Cycling-From Roubaix to San Remo: Scot's race against the clock across cycling's five classics

Ultra cyclist James MacDonald's previous feats have often involved soul-destroying hours lapping velodromes but on ​Sunday the intrepid Scot sets out on a much more scenic record ​attempt.

The Google software engineer plans to ride five of the ‌toughest ​one-day races in professional cycling -- back-to-back in four days -- starting with the iconic 258km Paris-Roubaix. He will then tackle the fabled cobbles of the 278km Tour of Flanders, followed by the Liege-Bastogne-Liege and Il Lombardia before finishing on Wednesday with the 298km Milan-San ‌Remo.

In total MacDonald will cover a combined 1,349km across France, Belgium and Italy -- with his only rest coming during transfers between the different routes in the support vehicle. "There's a big difference going from A to B instead of going round in circles," the 55-year-old MacDonald, whose bid to set a new indoor record for 100 miles was wrecked by illness at ‌the London velodrome two years ago, told Reuters.

Riding the five so-called cycling Monuments back-to-back has never been officially done before so, however long it takes him, with transfer ‌times included, it will set a benchmark for future challengers. MacDonald has competed in endurance cycling events for more than 20 years. He once completed the 3,089-mile Race Across America as a solo rider in 2016, set the fastest recorded return time between John O' Groats and Land's End in 2017, and broke the indoor 100km record in 2021.

Last year, as a warm-up for his five monuments challenge, he added his third Guinness ⁠record for ​taking the shortest time to ride the 625km ⁠between Scotland's most distant points -- Mull of Galloway to John O' Groats. DEFINING ONE-DAY RACES

"Of all the challenges I have taken on, this feels like the one I have been building towards," MacDonald, who has spent ⁠two years planning the ride in conjunction with the World Ultra Cycling Association (WUCA), said. "The Monuments are the defining one-day races in professional cycling, and nobody has attempted all five back-to-back in this format ​before. With the clock running continuously, every decision will matter, from how hard I push, when I sleep and how quickly the team can move me ⁠between routes."

The longest transfer will be from Liege down to Bergamo for Il Lombardia and one strict condition from WUCA is that a tracker ensures no speeding on the motorised sections. "Those 10 hours off the bike (between Liege ⁠and ​Bergamo) will be tough, especially after 700km on the bike, that might feel awful," MacDonald said.

MacDonald has never ridden any of the five routes but says the weather forecast in France and Belgium could make it feel more like Scotland although riding the lumpy bergs of the Tour of Flanders at night could be disorientating. But the roll ⁠down to the Mediterranean on the Ligurian Riviera will be something to look forward to.

"The pacing plan is that I'll hit the coast at sunrise. The profile for San ⁠Remo basically uphill and then it drops ⁠off a cliff as you get towards the Mediterranean." Despite riding in Europe's culinary hot spots, MacDonald will not have time to indulge and will follow the advice of his nutritionists who are part of the support team led by challenge manager Matt Jones of ‌Perpetual Sports Consulting.

"It's going to ‌be pretty systematic for me," he said. "Energy gels, brioche buns, croissants, energy powders, chocolate milk. ​And lots of coffee."