MT HOOD & THE
COLUMBIA RIVER GORGE
Jonsrud Viewpoint

Brotherhood, Bigfoot, and Backcountry Thrills: My Unforgettable Mt. Hood and Columbia River Gorge Adventure

Author: Jeff Jenkins @chubbydiaries
From the classrooms of Austin, Texas, to the sprawling landscapes of continents far and wide, Jeff Jenkins embarked on a journey that would redefine what it means to travel. Chubby Diaries, born from Jeff's own experiences as a plus-sized traveler, stands as a testament to his dedication to making travel accessible, enjoyable, and inclusive for everyone.
Getting ready for snowmobiling at Mt. Hood Outfitters

Every now and then, a trip comes along that doesn't just change your scenery—it changes you. But not every trip transforms you the same way. For me, it all depends on the places I visit—and how those places welcome me in return.

That’s exactly how it felt when I explored Mt. Hood and the Columbia River Gorge.

This wasn’t just any road trip. This was the road trip of a lifetime, made even more special because I shared it with my brother. We cruised through snow-capped mountains, wandered charming little towns, devoured unforgettable meals, and most importantly—laughed until we cried. There were moments we lost track of time, chasing Oregon’s hidden treasures, only to find lasting memories instead.

North American Bigfoot Center with owner Cliff Barackman of the TV show Finding Bigfoot

Our adventure kicked off at the North American Bigfoot Center in the town of Boring, Oregon—which, let me tell you, is anything but boring. The place was filled with quirky displays, life-sized footprints, and wild Bigfoot theories that sparked our curiosity and sense of wonder.

This little gem of a stop set the tone for the whole trip: a blend of mystery, fun, and discovery.

I’ve done some wild things on my travels, but snowmobiling through Mt. Hood’s backcountry? That was a first. My brother and I suited up, hit the trails, and raced across fresh powder with towering trees and endless skies surrounding us. The quiet of the forest mixed with the adrenaline rush—it left me feeling both grounded and electrified.


After the thrill, we found balance at Edgefield’s Ruby Spa, floating weightlessly in warm saltwater, cool mountain air brushing our faces. It was the reset we didn’t know we needed.

Pizza at Grateful Vineyard

Now, let’s talk food. Honestly, the meals on this trip? Next level.

We fired up our appetites at Skyway Bar and Grill, indulging in smoky BBQ, then treated ourselves to the frosé and soft-serve combo at Sugarpine Drive-In. From the mountains to the gorge, my brother and I ate our way through the Pacific Northwest.

Here are a few bites I can’t stop thinking about:

Every spot welcomed us like family and left our bellies—and hearts—full.

Jonsrud Viewpoint in Sandy

Yes, Mt. Hood and the Columbia River Gorge are stunning, but what made this trip magical were the small towns—Troutdale, BoringSandy, Welches, and The Dalles. These hidden gems are the soul of the region, often overlooked but unforgettable.

One moment stands out: standing at Jonsrud Viewpoint in Sandy, soaking in the breathtaking view of the Sandy River Valley and Mt. Hood in the distance. What made it even more special? They provide color-vision deficiency glasses so everyone can fully experience the beauty of those colors. That’s the kind of thoughtful touch that stays with you.

I went into this trip thinking I’d check a few things off my list. Instead, I found myself leaning into the journey—letting go of the checklist and embracing every moment.

From sipping cider with a view to chasing thrills in the snow, this adventure connected me deeper to the land, the people, and even to myself.

So, if you’re searching for something new? You’ll find it in the places less traveled. I found it in untouched snow, the warm smiles of strangers, and the meals shared with my brother.

And I have no doubt—you’ll find it too.

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