Paddler Ben Stookesberry on Doing Deadly First Descents—With a Smile

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This article was produced in partnership with Eddie Bauer

Ben Stookesberry is the king of first descents. For the last two decades, the Montana-based kayaker has been the first person to navigate more than 130 river sections in 40 countries—and counting.

In the fall of 2021, he and a team of international kayakers, including fellow Eddie Bauer ambassador Chris Korbulic, made the first descent of the Rio Chalupas in Ecuador. Dropping 10,000 feet—from the Andes to the Amazon—in less than 50 miles, it’s one of the steepest, most intense rivers on Earth. It was the hardest expedition of Stookesberry’s illustrious career, which is saying something. In his quest for unpaddled rivers, he’s crossed the Greenland Icecap, climbed in the Himalaya, and survived a kidnapping by Columbian guerillas.

“The Chalupas is in one of the most unpredictable and dynamic environments found on Earth,” says 44-year old Stookesberry. “There’s no stable weather. There was a blizzard at the put in, tropical jungle at the bottom, and incessant rain storms and flash floods. You’re kayaking in a canyon where there’s no way out except downriver. But the jungle and narrow canyon mean you can’t scout the rapids until you’re right on them.”

It’s the kind expedition that Stookesberry loves. “They fulfill my boyhood dream of becoming an explorer and going to places no one has gone before,” he says. In such environments, Stookesberry excels like few others. But he insists his secret to success doesn’t rest entirely on his kayaking skills. It’s just as much about his attitude.

Men’s Journal: What draws you to expedition kayaking?

Ben Stookesberry: The kayak is the ultimate vehicle—because rivers are the most ubiquitous features on the planet and the last unexplored crevasses. Some of these places have never seen a footstep or paddle stroke. Kayaks are the only vessels that can explore them. I also like that these are multifaceted missions. When there are lots of unsurvivable rapids, there are lots of portages. It goes from paddling to canyoneering. You’re using ropes to scale canyon walls and machetes to hack through the jungle. You’re breaking down the expedition into parts; planning logistics, safety and strategy; looking for weather windows; and acclimatizing. It’s more akin to a big expedition in the mountains.

How important is your mental state on these kinds of expeditions?

It’s everything—similar to any challenge in life. It’s impossible to be successful and persevere without hope—hope of success and hope of reward. You’ve got to appreciate the one-of-a-kind aesthetics of a place.

What does hope look like for you?

Optimism. If you’re intentionally going to a place that’s thought to be impassable and unrunnable, you inevitably need optimism to figure it out. When rain starts, the cliffs close in, and rapids become an impassable jumble of rock. Hope fades to stark reality—so you need to have optimism to fall back on.

How does optimism change your perception of the situation?

You’re not running from risk. You’re confronting it. And you’re treating it like an opportunity and not as something to be avoided. Is my optimism sometimes borderline unrealistic? Absolutely.

Are you always optimistic?

On the Chalupas expedition, I struggled every single day to stay optimistic.

How did you overcome those low moments?

I’d try to find the joy of being in the place. It’s also helped that our group worked well together. The key was keeping good communication going. We’d take turns reading to each other. We’d play cards, and we always ate together—anything to keep the mood light and keep our mind off what was going wrong at that moment. Luckily, not everyone was low at the same time. There’s a natural flow to these things, but it’s also intentional. If you’re the guy who’s always left behind, it’s impossible to keep up a good attitude. Everyone took turns scouting, cutting the path through jungle, leading on river and cooking. Sharing the work load seemed to get us to the finish line with everyone and all the equipment intact.

Speaking of, what’s your favorite piece of Eddie Bauer gear?

The Super Sevens layering kit is rad. It’s a wind jacket, rain jacket, and fleece hoodie—pretty much all the layers I need on an expedition. It’s super lightweight and packable, and has me covered to a few degrees below freezing, which is about as low a temperature as we encounter on a river trip.

Your favorite saying is “Kayaking, like life, exists between ‘swims.’ ” What do you mean by that?

There are unavoidable challenges that you’re going to face on the river—and in life. You can diminish the difficulties as much as possible, but no matter how careful you are, inevitably you’re going to swim. That’s a metaphor for life. You’re going to fail and you have to find ways of moving forward.

What’s next?

I’m really excited that the Chalupas expedition is going to be made into a TV show for HBO. It’s cool that a mainstream audience is going to see what expedition kayaking is about in 2022.

Where do you go from here? Any future river trips on your list?

There are a lifetime of rivers to explore. As my physicality wanes, I hope to transition to the stories rivers tell beyond the personal challenge—to what they say about the changing planet.

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