Outfitters Forging Adventures on New Frontiers—And the Gear They Carry

Outfitters Forging Adventures on New Frontiers—And the Gear They Carry

Produced in Partnership with Filson

The final step onto wind-whipped ridgeline, a wild river churning down a deep and rocky gorge, a grizzly devouring a flapping salmon: Nature makes memories, and the best views often come from the most arduous approach, the most remote expedition, and knowing nature’s secret spots. A great outfitter or guide enables everyday adventurers to forge new frontiers.

Like Filson’s first customers in 1897, these three guides and outfitters blaze their own trails, refuse to accept the status quo, and elevate the places they work and the people they guide. They also depend on no-compromise gear to make every adventure a success.


Born and raised in Girdwood, AK, 32-year-old Desi Sherwood has been guiding since he was 19 years old. He grew up backcountry skiing in the winters and running rivers, camping, fishing, and hunting in the summers in the 49th state, honing his skills while immersed in the rugged, unforgiving beauty of Alaska’s wild lands. Today, he is one of Alaska’s most esteemed fishing guides.

On Guiding
I have the unbelievable fortune to work all over Alaska and to access the most remote and wild zones by helicopter and small plane. My guests and I fish pristine, undiscovered rivers where it’s unlikely we’ll see another human, where wildlife abounds.

Cultivating outdoor skills is empowering. I want my guests to feel accomplished. I won’t hold your hand all day, but I will take the time to teach you to be stronger and more confident outdoors and in life.


My dad worked hard, planning to retire early to follow his postponed dreams. He passed away before he got the chance. That was an eye-opener for me. Life is short and meant for living. My goal is to be proud of how I spend every single day.

[On every trip, Sherwood notes that he always brings his gun, his fly rod, and a PMA—that is, a positive mental attitude.]

Desi Sherwood Alaska fishing guide
courtesy Filson

Wild Encounters
I’ve had many bear encounters—some fun, some scary, all memorable. I’ve learned the sound of fighting bears, hungry bears, curious bears. I’ve had bears sniff my feet from outside my tent.


Alaska Fishing Essential:

Filson tin cloth fishing pack

When you’re fishing prime waters all day, Filson’s Tin Cloth Fishing Pack carries everything you need, made of rugged waxed canvas to resist water—or other muddy, sandy elements you drag it through. Stash tools and necessities within internal pockets, and fold out a work surface for holding and repairing flies. A pair of outer pockets work well for water bottles or other daily must-haves.

Shop Now

Survivalist, big game hunter, upland bird hunter, fisherman, philosopher, co-host of USA Network’s ‘Mud, Sweat and Beards,’ and Washington state homesteader, pig farmer, husband, and dad, Ray Livingston is a complex character who is guided by his strong belief that every encounter and experience is part of nature finding balance and moving towards a greater good.

Ray found his passion for living from the land when he withdrew into the woods and traded the comforts and constraints of modern life for simpler priorities and practices. History Channel’s ‘Alone,’ which drops individuals to survive with rudimentary tools and no outside assistance, sent Ray to Great Slave Lake in Canada’s Northwest Territories for 19 days. Now Livingston splits his time sharing his eclectic spirituality, co-hosting his own survival show and farming.

Filson Ray Livingston


On Saying “Yes”
Cool stuff and interesting experiences just seem to come my way, I try to say “yes” when an opportunity presents. I like to share my experiences living in harmony with nature with people, I like to show my struggles in a positive light and to show there is always hope. Life is a story of overcoming odds, staying positive despite our struggles, and realizing the blessings in the outcome of any situation.


Finding Peace in the Woods
In 2016, I lived in Portland, Oregon, but didn’t feel at home there. I bought a travel trailer and moved into the forest and out of modern society. I went to town for work, but I spent lots of time in the forest. I accepted that my life might be a solitary one; I got comfortable with being alone, and I found peace. The ability to love unconditionally starts with loving yourself unconditionally. Now, I accept that everybody on this planet has a role, whether I agree with them or not, whether I like them or not. As humans, we can’t see the big picture, but nature has a master plan. Humans are not separate from nature; we are part of it. I don’t approach nature as an adversary but in harmony. When I am in nature, I show and express my gratitude, and whatever I need seems to show up. I’ve harvested my largest elk, deer, and grouse after I’ve paused to be thankful for nature’s intricate workings and incredible bounty.

Filson backpack strap


Learning How To Live From Nature
I try to gain an understanding of the ecosystems I see by observing. I think about why certain plants grow where they do and why animals do what they do, and how elements of the ecosystem support each other. I apply my observations to the mundane world. When I am considering what is right, or how to do something the best way, I look to nature and gauge my actions based on what I find there. For example, you never see a deer sad. Sometimes it’s wary, but deer go through their life happy. They don’t let fear of danger overrun their lives as humans do. Like a deer, I accept danger is real, but I don’t spend my time being fearful. I deal with threats as they happen, then go back to normal life and enjoy what I do.

Ray Livingston Camping


Farmer’s Friend:
In my life as a North Country farmer, I work in and I live in Filson wool and Tin Cloth. I wear Tin Cloth Pants and Jacket every single day. I use them hard, I trust them for my survival, and they’ve never failed me. My Oil Finish Double Tin Cloth Pants, Filson’s double-stitched, roomy-cut, toughest pair of pants, are as essential to me as a good knife and my multitool. Without pants, knife, and tool I feel naked.

Filson vest

The Oil Tin Cloth Vest is made with the same rugged, water-repellent finish, cut roomy for unrestricted layering with pockets for hand-warming and extra tools.

Shop Now

A lifetime musician and outdoorsman, Chuck Ragan has always wandered but he’s never felt lost. Both music and the water ground him and give his life rhythm and flow. He started fishing as a kid, and even when his post-punk band took him on the road for the better part of 25 years, he always had his fly rod, and always found a riffle to cast or a hatch to match, even in unlikely places. When his son was born, Ragan stopped touring and started guiding professionally in his adopted home state of California.

Filson guide Chuck

On Music and Fly Fishing
Music and fly fishing have always gone hand in hand for me. I seem to find the same sort of peace from both. I have spent the greater part of my years living outside of the norm, including following my passions in life and figuring out how to make ends meet doing it. I’ve been guiding since 2015 but have been taking people fishing for many years. The path to professional guiding from music was a natural shift, though to some it seemed I made a major mid-life career move mid-life. To me, being an independent worker is the same across fields. I still have the same goals and the same approach to business. The music business tends to take me further away from my family. The guide business keeps me closer to home.

Filson florida chuck outfitter canoe

On Sage Advice From an Elder
When I was a boy, my grandfather told me that if there was something that I loved to do, I’d be a damn fool to ever put it down or walk away from it. I remind myself of that advice every day. My goal on my trips is to share the outdoors, pass on the ethics and importance of how to take care of our waterways, and to pass on knowledge and insights that were passed on to me, including the advice from my grandad.

Chuck filson fishing


Salt Marsh and Shallows Standby:

Filson dry bag

The water and boat work are tough on gear. So is being on the road. I choose gear I can depend on, gear I know will work for me and my clients. Protecting gear from water and dust is critical for any adventurer. Filson’s rugged roll-top 54-liter nylon Medium Dry Duffel provides submersible storage tough enough to survive the rigors of life at sea, dusty trails in the back of a jeep, or a flight in the hold of a bush plane. Webbing handles wrap under the load for easy carry.

Shop Now


For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!

Leave a Reply

Your email address will not be published. Required fields are marked *