Desi Sherwood: Off the Grid

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Finding your passion can be a lifelong journey for some, but as simple as walking out your front door for others. For guide Desi Sherwood, growing up immersed in the Alaskan wilderness surrounding his home in Girdwood, Alaska (population 3,000), he knew from a young age that his true calling was being outdoors.

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Winters were spent ski racing at nearby Alyeska Ski Resort, and he whiled away summers jet boating, rafting, and fishing the multitude of waterways nearby. But it is said that passion and pain often walk hand in hand. During his early twenties, Sherwood experienced both when his father passed away suddenly, much too young. He decided to forgo a conventional path and forge his own trail in the outdoors. “The unknown is scary for anyone, regardless of their skills, but I knew that to be happy, I would have to follow my heart and live my life for myself,” he says. “By saying yes to any opportunity that came my way, I soon found myself on many grand adventures.”

There is an aura of competence surrounding the bearded Sherwood these days. His every movement seems to have a purpose.

Years went by as he honed his skills, deep in the savage beauty that is Alaska. Countless hours were spent pulling oars on rivers, leading clients down steep ski lines, chasing grizzly bears away from fly fishermen, and doing all the dirty work in campsites. Digging latrines and hauling gear can be exhausting, but it’s less so if you love your job. Through it all, he kept absorbing lessons and making friends. His bank account was always lean—rarely do riches follow guides—but his experiences more than made up for that shortcoming. As his skill set expanded, he became someone people searched out, someone they trusted to plan a memorable outing and adapt on the fly. He was hired on at the legendary Tordrillo Mountain Lodge, where he spent his winters and summers flying into remote locations with clients to share experiences with them, ones that they would never have in their regular lives.


“Watching someone light up after catching a fish or skiing an untracked line is what fuels me,” he says. “There is nothing better than spreading the stoke and sharing the realization that anything is possible.”

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There is an aura of competence surrounding the bearded Sherwood these days. His every movement seems to have a purpose. When Filson first met him several years ago on a photoshoot, they immediately asked him if they could include him: he was the real deal. He understands what it takes to succeed off the beaten path, how to embrace the wilderness, and the value of the right gear when off the grid. He has since collaborated with Filson on numerous projects and organized the trip featured in this issue of The Filson Journal. As he glances toward the horizon, he can see many other adventures he wants to take. In particular, a multi-day fishing expedition through the remote Brooks Range in northern Alaska keeps drawing his attention. It would be “brutal and beautiful”, he says—a combination that he knows well.

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