As if that wasn't a difficult challenge enough, runners must fight elevations of over 7,500 feet across the tricky routes that follow the Cleveland path from Guisboro to Helmsley.
Technical terrain, mixed weather bags and tight time cutoffs all add to making this a truly epic challenge.
Ryan won with an incredible endurance show, crossing the finish line as a third-place competitor in 8 hours and 21 minutes, just 10 minutes behind the leader. His average speed was only nine minutes per mile.
Boydblood also finished an incredible performance in 12 hours and 2 minutes.
To put results in sight, the slowest finisher took 16 hours and 43 minutes, with over 50 people unable to finish the course.
On the other side of the world, Andrew Bates and his wife Chris joined the 800 people and ran the Middle Earth halfling marathon.
As the name suggests, this half marathon brings the runners an incredibly beautiful setting for New Zealand's Lord of the Rings films.
Andrew and Chris thoroughly enjoyed running through Hobbiton and other areas in Shire, especially the Green Dragon food and water station, crossing the finish line in four hours.
Close to home, Sean Imeson took on the Sheffield Half Marathon, a popular annual road race with nearly 6,500 competitors.
He crossed the finish line in 1 hour and 57 minutes and placed it well in the top half.
Paul Hickman chose the Humber Bridge Half Marathon for the Sunday Race, crossing the finish line in 1 hour and 42 minutes.
Elsewhere, Jessica Chadwick and Spaniel Hobbs competed in the Canoc Chase Cannicross 10K.
For both Jess and Hobbes, it was the first crabcross – a cross-country race with the dog – and both felt fun.
Despite Hobbs' inability to run in the straight, they finished seventh overall with 56 minutes and 58 seconds.
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