Portland to Wisconsin in 30 Days: A Road Trip Across America

One car. Two people. Thirty days to see if the road would bring us closer or pull us apart.

Every time I set out on an adventure, my mind drifts back to a moment I once lived.

It was summer. I was cruising along a rural highway, windows down, wind howling in my ears like violent whispers.  I can’t remember where or even when exactly, but that doesn’t matter.  What matters is that I was there.  Present enough so much so, that it is now a part of who i am today.   

The sun was setting, low and blinding, glaring into my eyes, but I didn’t pull the shade.  I was passing through a grassy field, the type that is hip height and sways in the wind, heading toward a wall of trees where the land behind them rose like a blanket over the hips of a sleeping woman.  Through my squinting eyes, i saw the swaying grass bathed in a golden light, glistening like honey.   That’s the scene and it’s stayed with me.  For years I’ve tried to recapture it.  Tried to pull that moment out of memory and experience it once again.  

I’m not sure what part of it shakes my soul, maybe it was the landscape and the fact i had nowhere to go or timeframe to get there.  Maybe something deeper.  Something that lives beyond the veil of ourselves. And over the years, I kept going.  Kept leaving.  Chasing that feeling.  Down more unfamiliar roads on more warm summer nights and I started to realize that no matter which road nor which time of the day, it was the action of going that stirred my soul.  That what i was looking for wasn't along a road at all, rather it was a way of thinking, or maybe a way of not thinking.  

Burning down the house of “knowing” in exchange for the fire of not knowing.

Every great journey ends in suicide.
Killing who you were and giving birth to who you are.

So call it a beginning,
But it’s not the first page.
It’s the tearing of the page before it.

This trip was a first for Nicole and me and it sure as hell will be good test since we’ve only known each other for five months and now we were about to cram our sorry asses into the tin can of Ravie for a whole month.   

Thirty days of close quarters, stinky-ass morning breathe, digging a hole in the woods to take a morning shit while the other spoons chunky yogurt into their mouth, staring wide-eyed at last night’s undigested corn and the rising steam as their warm poo hits the cold waking earth and testing the hell out of Ravie’s creaking springs every goddamn night.  You never really know a person until you’ve spent a week trapped in a metal rat’s nest, watching what kind of strange beast crawls out after midnight.

Two smiling people sitting on a wooden deck with a white railing, surrounded by green trees, holding drinks and posing for the photo.

Once we’d gutted Ravie of the sad-solo-man build, plywood, mildew and all, we had to figure out how to cram two people’s entire lives into a 2012 Toyota RAV4 without losing our minds or each other.  We kept what worked, scrapped what didn’t and Frankensteined together a setup made for two.

👉 See the full build of Ravie here

We weren’t just building a tiny house on wheels, we were building a launch pad toward something unknown and untethered. Such as the vast belly of America stretches out East of Portland, three million square miles of freedom.   A freedom not just to think or dream, but to act. To take freedom from the abstract abyss and put it into practice, into motion, to hammer it into the material world with a calloused hand and a shot of whiskey.  Freedom to invent, to rebel, to shit your pants at 30,000 feet and let is fester as you watch with a stoic face and a pair of aviators your fellow seat-mates squirm and wrinkle their nose from L.A. to JFK.  

America is a playground for evolution, both messy and magnificent, touted with imperfections and disagreements.  A place for ideas; brilliant, absurd and sometime catastrophic, to be conceived, born and nurtured for however long and through whichever path, until they are brought to fruition and set loose upon the world.  Ideas that have, (for better or worse) propelled humanity in the direction it is destined for.  Ideas such as the Lightbulb, the telephone, the airplane, the internet, each an invisible seed that took root in somebodies big head as a thought, a thought turned to action that still flows with momentum today.  

And then there’s the final, most American idea of all:

The idea to leave.     

After we said goodbye to my brother and girlfriend, we hit the open road, the road to freedom…

The Route: America Unfolds

Google Maps estimated the drive would take around 62 hours, which we stretched into thirty-one days.  Covering close to 4,000 miles.

The equivalent of driving from New York City to Anchorage, Alaska or the circumference of France, twice.

Throughout the trip, we used the website/app ioverlander, an invaluable tool to scout essential resources on the road.  everything from potable water sources to overnight camping spots. Completely free to use, iOverlander relies on a community of travelers who share real-time updates, reviews, and GPS coordinates, making it an excellent companion for vanlifers, overlanders, and road-trippers alike.

That said, it’s always a bit of a gamble, some locations may already be occupied when you arrive, and others might sit a little too close to noisy highways or be in less-than-pristine condition. But then there are completely free gems, like these.

We stretched the 62 hour drive into 31 days.