Great Running Challenges

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The classic summer beach fortnight isn’t for everyone, least of all runners, who tend to find their minds wandering into fantasies of racing in more exotic locations, often pushing themselves harder and discovering fresh levels of suffering. These are some of the epic runs that occupy their dreams.

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The Race That Took 20 Years To Be Repeated: Berghaus Dragon’s Back Race

This infamous race takes place along the mountainous spine of Wales over five days. The route covers 300km with 16,000m of ascent across wild, trackless, remote terrain from Conwy Castle. The original Dragon’s Back Race took place in September 1992, but was not repeated until 2012. With a combination of unforgiving terrain, typically challenging weather and sheer distance, this is justifiably considered to be one of the hardest mountain races in the world.

Damian Hall ran it: “The most challenging thing about the Dragon’s Back Race is the navigation. And the 16,000m of ascent. And the cut-off times. And all the effing midges. The distance is the least of your worries, but the scenery is pure Hollywood at times. The organisation is very slick, with great food and lots of thoughtful touches, such as starting at a dramatic castle and free ice creams. A once-in-a-lifetime race and a dream holiday.”

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The Race You Are Least Likely To Finish: The Barkley Marathons

The Barkley Marathons are widely considered to feature the hardest 100-miler in the world. Started in 1986, only 14 runners out of about 800 to enter have ever completed the 100-mile race within the 60-hour cut-off. The race is in Frozen Head State Park near Wartburg, Tennessee and was devised by “Lazarus Lake” Cantrell after he heard that Martin Luther King Jr’s killer, James Earl Ray, had escaped from prison in the Frozen Head State Park and only managed to cover 8 miles in 55 hours.

James Adams ran it: “The best thing about the Barkley Marathons is that the course is trying to win. It has quite a good success rate. From beginning to end, the way the race starts and the nature of the course, the whole thing is uniquely crazy.”

The Race Where You Run Around A Mountain: Ultra-Trail du Mont Blanc


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The UTMB is Europe’s most iconic mountain ultra. The race starts and finishes in the town of Chamonix and circumnavigates Mont Blanc, covering more than 100 miles. The course sees the participants climbing and descending more than 9,600m, through villages in three countries – France, Italy and Switzerland. The men’s record is held by Frenchman François D’Haene (20 hours, 11 minutes and 44 seconds), but don’t worry about trying to beat that.

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Tobias Mews ran it: “That moment when you’ve been running through the entire night, your morale is at an all-time low and then, just when you feel you can’t go a step further, the sun pokes its head above the mountains, casting a warm glow. It’s a memory I’ll never forget.”

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The Challenge Most Likely To End With A Pint: Bob Graham Round

The Bob Graham Round is an iconic challenge (not an organised race, so can be attempted at any time, clockwise or anti-clockwise) where runners aim to traverse 42 fells in the Lake District within a 24-hour period. It’s named after a Keswick guesthouse owner, who broke the Lakeland Fell record in 1932; the current men’s record of 13 hours 53 minutes was set by Billy Bland in 1982. You’ll need to be accompanied throughout the challenge if you want your attempt to be recognised by the official Bob Graham Club, where you’ll join an elite group of less than 2,000 successful fell runners.

Bruce Duncan ran it: “The Bob Graham is iconic, but fewer people have done it than have stood on the summit of Everest.”

The World’s Oldest Annual Marathon: The Boston Marathon


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John Graham, manager for the USA’s first Olympic marathon team, was inspired to start the event in 1897 by the Olympic marathon in Athens the previous year. Until 1972 the race was only open to men, although in 1966 Bobbi Gibb became the first woman to complete the course illegally. A year later Katherine Switzer registered with her initials and race director Jock Semple tried to manhandle her off the course mid-race – Switzer’s boyfriend Tom Miller body-checked Semple to allow her to finish.

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James Poole ran it: “After 120 years, the Boston Marathon is in the DNA of the people who live there. Everyone wants to know your story and to share theirs. Boston is like combining Parkrun with the Olympics. You have to earn your way there, but it really is accessible to everyone.”

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The Race Where Once Is Never Enough: Comrades Marathon

An annual race in the KwaZulu-Natal Province of South Africa, with the course travelling between the cities of Durban and Pietermaritzburg, this is the world’s largest and oldest ultramarathon. It was started by First World War veteran Vic Clapham to honour the South African soldiers killed in the conflict. The aim of the race is to “celebrate mankind’s spirit over adversity” with alternating “up” and “down” legs run in opposite directions.

Holly Rush ran it: “The thing I wasn’t expecting was 87km of continuous hills and 80km of barbecues/partying South Africans. There were a lot of drunk happy people on the course – it made for a party atmosphere.”

The Run Where You’ll Tackle Forests, High Altitude, Water And Extremes Of Weather: Te Araroa Trail


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Fancy taking on a 3,000km route stretching from Cape Reinga in the north of New Zealand to Bluff in the south, crossing the Cook Straight between the two islands? This is a trail that will push even the hardest adventurer to the limits and should only be undertaken with extensive support. It is too long between towns to run unsupported.

Jez Bragg ran it: “The Te Araroa Trail showcases New Zealand’s incredible landscapes, making long-distance travel on foot just pure pleasure. Most invaluable bit of kit would have to be a SPOT personal locator beacon. If you’re soloing through the wilderness like I was, you really need the safety net of emergency rescue if it hits the fan.”

The Race Where You Can Take Part In One Of The Largest Community Events In The World: City2Surf

The City2Surf is a 14km road race held annually in Sydney, Australia, and is one of the most visually stunning events you could ever hope for. The race started in 1971, with 1,500 runners. In 1991 Steve Moneghetti won the race for the fourth time in a row and set the course record of 40 minutes and 3 seconds, which still stands.

Ben Moreau won it: “I’ll never forget that feeling of grinding up Heartbreak Hill at 8km, with about 4km of climbing, and then with 2km to go, you see Bondi Beach below you. An amazing sight on any day but when you are broken by the hills, it’s even more amazing.”

Former contributor

Simon is a marathon runner. He took up the sport after quitting smoking and a generally unhealthy lifestyle, and now runs a social media marketing consultancy for running and endurance sports brands called Freestak. He is also publisher and editor of Like The Wind magazine.