Rupert took part in the official Indian Pacific Wheel Race in 2017 before it was stopped after well-known ultra endurance cyclist Mike Hall was fatally hit by a car in the race's final stages. Rupert made it to Adelaide at that point but the following year he completed the 5,500km journey from Perth to Sydney when an unofficial version of the race was staged (but not by original race organisers).
He has caught the ultra-endurance cycling bug and now turns his attention to RAAM.
"I want to race in the 2020 RAAM to create awareness about mental health and help raise funds for charities like Crossing the Line that work in mental health," Rupert said.
"The RAAM is one of the most challenging ultra-endurance bicycle races. Now 38 years old, it pushes entrants to their physical and psychological limits on a 3,000 mile (4,900km) route from the west to east coasts – from Oceanside, California and to Annapolis, Maryland.
"Mental health is an area that is causing greater concern by the year, and in so many areas of society. (It) is an area that I have experience in confronting; firstly, with my own issues with self-esteem and body image...and the eating disorder bulimia that eventuated from those issues and wrestle with today."
"I have written about this in one of my latest of 15 books, Overlander – One Men’s Epic Race to Cross Australia. It is based on my experiences in the riding in the 2017 and 2018 Indian Pacific Wheel Race, a 5,471km solo and unsupported bicycle ride from Fremantle to the Opera House in Sydney."
Before Rupert sets off on June 16 from California, he has a lot of training kilometres to complete, as these 'Road to RAAM' videos demonstrate - produced by Anthony Gordon.
Kilometres and kilometres of riding in the darkness and solitude or on the trainer:
plus a trip to Japan for some cross-training on the snow:
Rupert will also race Revolve 24 at Tailem Bend in Adelaide on 21 March as important RAAM preparation.
Head to Rupert's sponsorship page for more information.
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