Up, Over and Out is the craziest double-century bike ride you’ve never heard of

endurance bike ride Mt. Washington
On the first leg of Up, Over and Out, Mt. Washington looms ahead, waiting to be conquered. Photo courtesy of Thomson Riley

“Up, Over and Out.” Sounds quick and easy, right? In fact, it is neither. It’s a 200-mile (“double century”) bike ride traversing the state of New Hampshire from the Canadian border to the Seacoast — terrain that’s not exactly merciful.

And then, of course, there’s this one problem: Mt. Washington. It’s right in the way. That, ladies and gents, is the “over” — a casual stroll across the highest peak in the northeastern U.S.

When I first heard about Up, Over and Out, I asked, “How long does that take?” The reply? A single day.

Up, Over and Out was conceived by Jay Riley, an insatiable adventurer and obvious proponent of pushing one’s limits. He’s completed it three times.

“I like cycling, I love Mt. Washington — I’ve climbed it over 50 times, in all seasons — and I’m busy, so this accomplished a lot of what I like to do all in one day,” he says. “I like trying [things] that you don’t actually know if you can pull off. And I liked the route and concept: up to Mt. Washington, over the mountain and out of the country!”

The original route began in Portsmouth and ended just north of Colebrook, but finishing such a mission in the middle of nowhere was decidedly less agreeable than arriving in Portsmouth at sunset and cracking open a cold one. The sheer length of the ride means that it needs to happen in high summer — in this case, June 14.

Until last month, Up, Over and Out had been completed only by a lonely three people in about 15 years: Riley and his two friends, U.S. Olympic rower Kurt Somerville and Troy “Three Lung” Fenderson. Jay’s son Thomson, Matt Burke, Ryan Laperle and Jerry Hillard thought that they could use some company.

The decision to go was made spontaneously: “Ryan texted me 11 days before and basically told me I was doing it,” says Burke, 34. They efficiently enlisted the support of a sag wagon and sponsors, including Lagunitas, Untapped and Skratch Labs.

Jason Donald at Skratch Labs says, “It was funny; Thomson wrote with a spare few details about the ride, saying, ‘It should be fun-slash-stupid!’ I said, ‘Yeah, stupid is fun most times, and usually a chance to build some character.’

“Skratch [was a good fit for Up, Over and Out because our] products were developed in real-world situations not unlike what Thomson and his boys experienced, [to] help us get through the stupid endurance adventures we get ourselves into.”

bike ride
Jerry Hillard, Ryan Laperle, Thomson Riley and Matt Burke at the Canadian border, 4:40 a.m. Photo: Courtesy of Thomson Riley

Incredibly, the crew didn’t even employ any special training for this formidable journey. These guys average about nine hours on their bikes each week. “Biking endurance is sort of built into our legs,” 31-year-old Thomson says. “It [was] the hike that was the real question mark. I hadn’t been on a real hike since 2012.” And he was the only one who had previously summited Mt. Washington. (He did it for the first time at age 7 with his father, Jay.)

At 6,288 feet, Mt. Washington isn’t known for its extreme elevation. It is known, though, for being extreme, period. For a long time, Mt. Washington, located in the state’s White Mountains, held the distinction of having recorded the highest wind speed ever, anywhere — 231 mph — and the summit sees hurricane-force winds (more than 75 mph) for almost a third of the year.

In addition, the weather is highly unpredictable. Mt. Washington sits squarely within both major Northeastern storm tracks and its geology actually accelerates the winds that scale its face. The mountain is haunted by countless tales of untimely and improbable deaths — most tethered to the notoriously volatile atmosphere.

“We had absolutely perfect weather for both the hike and bike,” Thomson says. “There aren’t many days on Mt. Washington where it’s 50 [degrees] with zero wind at the summit!”

Is it possible to take a bad photo up there? #upoverandout #mtwashington @untappedmaple @skratchlabs

A photo posted by Thomson Riley (@thomsonriley) on

“It is just so beautiful up there,” adds 28-year-old Laperle, “and the experience was so surreal, knowing that we had 75 miles of cycling [and 4 miles of hiking] in our legs with [a 4-mile descent and] 120 to go.”

Of course, this strike mission of sorts would really have been crazy if it didn’t include moments of wavering heart. “I just remember staring at the ground for long periods of time wondering if my legs would keep going around,” Riley says. But after 16 hours of physical activity so grueling that it necessitated “meals” at half-hour intervals, the foursome crossed into the coastal city of Portsmouth elated.

With the exception of Hillard’s busted derailleur 60 miles from the finish, the day went remarkably smoothly.

“[The next day, I felt] like someone filled my entire body up with concrete, let it harden, then hit it with a Mack truck,” Laperle admits.

“I have done several 146-mile solo rides and some team 24-hour mountain biking races,” Hillard says. “But this was in a different league. It’s a bucket-list thing. In August, I turn 52, and the other guys are in their late 20s, early 30s. My point being, don’t ever think, ‘I missed my chance to do something like this.’ Get off the sofa and go make memories you’ll never forget. I would do this again in a heartbeat.”

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