What it’s like to complete ‘the world’s toughest bicycle hillclimb’ 34 times

When asked to describe the experience in one word, Mark Greenleaf offered two: "agonizingly rewarding."

Mark Greenleaf racing in the Mount Washington Auto Road Bicycle Hillclimb. Provided by Mark Greenleaf

It all began with a dare.

Mark Greenleaf was living in Providence in 1983 when he grabbed the mail before going out to dinner with friends. That’s when he noticed an article about New Hampshire’s annual Mount Washington Auto Road Bicycle Hillclimb in Bicycling magazine.

“After a couple of beers, we dared each other to do it,” said Greenleaf, 61, of Foster, Rhode Island. “The three of us signed up and we went. And the rest is history.”

Greenleaf will compete in the 49th annual Mount Washington Auto Road Bicycle Hillclimb on Aug. 20. It will be the 35th time he attempts the race, billed as “the world’s toughest bicycle hillclimb.”


The individually timed 7.6-mile race to the summit of Mount Washington attracts riders from around the world. Mount Washington, notorious for its bad weather, is the highest peak in the northeast at 6,288 feet.

“The Hillclimb features an average grade of 12%, with extended sections at 18% and culminates just before the end of the ride at a heart-pounding, leg-cramping 22%,” according to Tin Mountain Conservation Center, organizer of the event, which is its largest fundraiser of the year.

Greenleaf has been seriously biking since college, pedaling anywhere from 2,500 to 4,500 miles a year. But during his first race in 1984, he learned quickly that the race is a mental as well as a physical challenge.

Racers begin the Mount Washington Auto Road Bicycle Hillclimb in 2017. Joe Viger

“It was my first time going up Mount Washington by any means, so it was kind of an awesome thing in that regard,” Greenleaf said. “It was a nice day for Mount Washington. It wasn’t too cold and there were beautiful views. But at the same time, it was, ‘Oh my God, what have I gotten myself into?’ I’ve since learned that the race is at least 50 percent psychological.”

Spectators line the route, which is closed off to traffic during the race.


“The 22 percent is what they say it is,” he said. “It’s very difficult, that last stretch up the hill. But what makes it beautiful is that the crowd is there. There could be 100 or more people with cow bells and they’re screaming. That’s what gets you up that last stretch because you’ve been riding for 90 minutes, you know, and you are exhausted.”

The race is “heart-pounding” throughout, he said.

“There’s a little bit of a flat section right at the bottom and then you just go right into the hill, right into a very steep grade,” he said. “You don’t have your second wind right away and you’re breathing very heavily. And then as you get into the first half mile or so, at least with me, my breathing tends to calm down a bit but my heart rate is still way up there. “

It’s so tempting to stop and put your foot down, Greenleaf said, but he’s learned to push through that feeling.

“I stopped the first time I did it,” Greenleaf said. “I stopped a few times. But I haven’t stopped since then because it’s just miserable getting back on the bike.”


Once stopped, racers have to mentally get themselves back into the race, he said, as well as ride laterally across the road in order to get their feet back into the pedals while avoiding other riders and that can be difficult, he said.

He doesn’t listen to music while racing because he finds it distracting, instead he listens to an inevitable inner dialogue.

“I listen to myself yelling at myself,” he said with a chuckle. “I argue with myself. [I ask] ‘Why do you do this?’

The worst weather he’s had to endure is the rain, cold, and wind when the race used to take place in September. After some canceled races due to weather, organizers moved it to August, he said.

“With the wind chill, it’s been probably in the 20s, maybe in the teens,” he said.

He has raced in weather that was so cold that his legs would be “beat red” and feel numb from the wind, he said. One year, he finished just before it began hailing on the racers after him.

Greenleaf has made it to the finish line all 34 times, he said. It’s not uncommon to see riders stop the race and get picked up by the sag wagon, a vehicle that follows racers and picks up those who drop out.

“And I’ve seen people at that last 22 percent stretch, they’ll have to put their foot down because they can’t finish, and they’ll be halfway up that last stretch, and people will come out of the crowd and help them back on their bike and push them the rest of the way just so they can say they finished the race.”


Once at the top, due to the mountain’s grade and weather, racers must make the trip back down in cars.

Racers in the Mount Washington Auto Road Bicycle Hillclimb in 2015. Joe Viger

“I can legitimately say I’ve raced against Tour de France racers in this race, although I never saw them, of course, because they were way out in front,” he said.

Greenleaf is currently training in his basement on rollers, which he described as a treadmill for his bike. Come spring, he’ll move his training outdoors, at Wachusett Mountain and on various hills across Rhode Island and Connecticut.

“It’s a tremendous sense of accomplishment, really,” he said about reaching the finish line. “You have all this mundane crap you do all during the year and then you do this. At least in my experience, it makes me want to go back. Maybe when I’m three-quarters of the way up, I may be doubting myself and having arguments with myself, but once you’re done and you put your feet down, and hopefully you had a good time — I mean the literal time on the clock — you want to come back.”

His best race time ever: 1 hour and 14 minutes in 1992. Professional racing cyclist Tom Danielson, who competed in the Tour de France, holds the best record at 49 minutes and 24 seconds.

Greenleaf said he doesn’t expect to match his best time again, but now aims for completing the race in less than 90 minutes and said he will return to the race for as long as he is able.


When asked to describe the experience in one word, Greenleaf offered two: “agonizingly rewarding.”

Registration for the race opened March 1 and bicyclists can pay the $350 registration fee in its entirety or pay $150 and fundraise the remaining $200 by Aug. 7.


This discussion has ended. Please join elsewhere on