All The Fun Of The Oregon Trail Without The Dysentery

yours truly looking out on Smith Rock. Shop my favorite hat here.

yours truly looking out on Smith Rock. Shop my favorite hat here.

I’d never taken a cross country road trip before.

It seemed romantic to me though— in a nostalgic, Americana-kitschy kind of way. . . Full of roadside stands, funky statues and creations in small Southern and mid-Western towns that’d be boasting about “The World’s Largest” insert-something-random-here. Like a huge peanut. (read on to see if my dreams came true!)

We were getting ready to move from Virginia to Oregon, and actually I’d never even been to the state of Oregon until I crossed the state line; with a car full of belongings and a poorly-sedated cat, anxious but ready to start a new life chapter there with my fiancé at age 31.

Our Hyundai Santa Fe isn’t quite a Conestoga covered wagon, which is probably good. My only experience with the evergreen state was during the 90s, playing The Oregon Trail on a jewel colored iMac G3 in computer class in elementary school. And let’s be honest, by the time you reach Oregon you quickly float down The Dalles river and the game’s pretty much over.

This actually makes me incredibly nostalgic - let’s go find one on Craigslist and relive the glory days.

This actually makes me incredibly nostalgic - let’s go find one on Craigslist and relive the glory days.

TANGENT:

I named other passengers on the wagon after my closest friends and family members— which proved to be an excellent lesson to my eight-year-old-self about life & death.

That my beloved companions could drown or get yellow fever was wacky to me. Whether I was ready to deal with it emotionally or not, several of them got dysentery, died, and left me (to forge ahead alone on the Oregon Trail) forever.

If you have never played The Oregon Trail the previous sentence made no sense and I apologize.

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Was it really just like the game, you ask? No, definitely not. Not in the least. Here’s a fun video from Weird History’s YouTube channel about real life on the real life Oregon Trail.

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My fiancé grew up in Richmond Virginia and I lived there about eight+ years. We love it tremendously but were ready for a new adventure. When we got the offer to come to Bend Oregon the turnaround time was fast, and we spent about two weeks running at full-sprint packing, planning, prepping— trying to find a place to live over the internet, etc etc.

If you’re never planned a last-minute

cross-country move. . . it’s a doozy!

Not wanting to drive a U-Haul or other moving van/truck ourselves, we opted to move with ABF which was a little more economical than some of the other moving companies, too. They have a few moving options - we opted for the trailer delivery, where they drop off the back of an 18’-wheeler and you pack your boxes up then seal it off and lock it and they pick it back up and deliver it to your destination.

  • Pros: You don’t have to drive a giant-ass moving truck across the country. You don’t spend money on gas for aforementioned giant-ass moving truck.

  • Cons: Our giant-ass moving truck arrived 2-3 days after we arrived in Oregon - so we did have to go without our stuff when we first got there, but we had all of our essentials in our personal vehicle so we were okay “camping out” in the house for the first few days.

Photo by anja. on Unsplash

Photo by anja. on Unsplash

We felt anxiously excited. we felt like the universe called us out West and we were lucky enough to be available to take the call.

Our first stop on the trip was to music-city, Nashville Tennessee— for the perfect timing of my childhood best friends’ wedding. We spent the day reuniting with friends and family to explore Nashville, spend some hours together before our epic road trip/move really began, and to celebrate a truly beautiful wedding.

After we married them off, rejoiced, danced, and cried to their first dance —

(which was amazingly to Kci & Jojo’s “All My Life” — middle school dance attendees everywhere, rejoice)

— we continued onward.

Nashville Mural perfectly placed right by my dear friends’ wedding venue. Source: my own photo.

Nashville Mural perfectly placed right by my dear friends’ wedding venue. Source: my own photo.


Our adventure was fun and quaint and full of anticipation for what lay ahead. We listened to lots of our favorite songs, lots of Spotify, and many of our favorites old and new.

But The anthem of our road trip (and most played song) was Midnite String Quartet’s cover of Sprawl II “Mountains Beyond Mountains” by Arcade Fire.

I’ve attached a video here so you can listen. Imagine yourself rolling through wheat fields or across a mountain valley in a covered wagon. It’s such a beautiful cover, we listen to it whenever we’re driving across a beautiful vista.


The Midland Railroad Hotel in Wilson Kansas. Established in 1899.

The Midland Railroad Hotel in Wilson Kansas. Established in 1899.

Our second stop was in the tiny —and surprisingly charming— town of Wilson Kansas, where we stayed at the Midland Railroad Hotel, which was established in 1899 and still has a lot of its original charm. I was seriously surprised at how cute it was!

Because we were traveling with our fur-baby and winding up in whatever town was fourteen hours away from the previous night’s town, the choices for hotels & air bnbs was narrow. . . so we were very grateful to find a place with some history and character that was pet friendly and happy to accommodate our late night arrival.

We drove and drove and drove and reached Wilson around sunset. Fortunately we arrived just before their restaurant closed, and they were once again super friendly and accommodating at my last minute dinner order, which we ate upstairs exhaustedly in our little historic hotel room.

Wilson Kansas is also home to

— wait for it —

the world’s largest hand-painted Czech egg!

I was BESIDE myself with glee to see a “World’s Largest” anything on our road trip! It seems like you have to stop at one of those for it to be a true American cross-country road trip.

WORLD’S LARGEST!!! My heart exploded with joy. “Largest hand-painted Czech egg” Source: my own photo.

WORLD’S LARGEST!!! My heart exploded with joy. “Largest hand-painted Czech egg” Source: my own photo.


We left Wilson Kansas early in the morning, marveled at the World’s Largest Handpainted Czech Egg, and kept driving. Hours of wheat and grain fields, which I actually found to be quite beautiful in a vast ocean-like kind of way; within a few hours into the flats of Eastern Colorado. We were excited about this day because we’d be driving through some mountainous parts of Colorado, which I hadn’t been to in years. (Actually the only time on our trip that we got stuck in any traffic whatsoever was in a beautiful mountain valley by a river in Dillon, Colorado.)

Our final destination was somewhere tiny in Utah a ways past Moab, I don’t even remember. The last few hours on the road before we got to our hotel were beautiful; the sun was setting on all of the red rock around us, making them almost glow, and the sky was starting to get hazy from the wildfires burning hundreds of miles away in California. Things were starting to feel very much like the Wild Wild West.

I think we stayed at a Best Western and I had to ask them to change our rooms twice because it smelled like cigarettes. But we were so exhausted from being on day four of driving 13+ hours a day and anxious to be in our new town. . . I told Kevin I only really needed a flat surface (that didn’t smell like cigarettes) to sleep on for even a few hours. I took a shower and was asleep instantly.

Photo by Gerson Repreza on Unsplash

driving through Colorado + Utah was beyond beautiful.

As a kid I remember heading out to Colorado several times with my family to explore and to visit my grandparents who lived in Castle Rock. They took us to Pikes Peak (where I promptly fainted at the summit), hiking in the Rockies and along the Continental Divide, and to Red Rocks Amphitheatre and Garden Of The Gods— where we would scramble up and down the steps, rock spires, and giant boulders.

A hazy Utah sky. Source: My own photo.

A hazy Utah sky. Source: My own photo.

Later we went to Utah to visit Mesa Verde and Arches National Park, and my Florida kid brain could barely comprehend the beautiful and Martian redrock landscape. . .

It was one of the first times I remember feeling utterly dwarfed by Mother Nature.

During the cross-country move we hardly stopped. Sure, I fantasized about Catty becoming a leash-trained hiking + adventure cat like Suki on instagram — and maybe if I asked the stars to align she would not flip out and mutiny against me? Nope.

She finally started to relax around day 3-4, you know. . . when we were almost there and it didn’t matter anymore. She was a good enough travel companion though. No yowling or crazy meowing or whining. Just a big time Oregon Trail scaredy cat.

SUKI THE ADVENTURE CAT! Follow Suki here

SUKI THE ADVENTURE CAT! Follow Suki here

So alas, we drove and didn’t stop. No leashed-cat hiking adventures.

We drove through the wild, red, gold, and orange hazy Utah backdrop, and I promised my fiancé we’d come back some day so we can explore the desert together.(And so I can come back to re-visit arches national park!)

We woke up eager to get going on our last and final cross-country drive day. By evening we planned on being in our new home: Bend Oregon.

By day four of being on the road we were getting good at the long days of driving in shifts; enjoying the scenery and the new places, listening to lots of great music, and daydreaming of the very near future.

We’d also spent the previous few days on the road also taking turns, like good responsible adults, calling Bend to get all our necessary utilities hooked up. But as fun as the road trip was, our bodies were stiff and worn out from sitting so long and I don’t think we could’ve possibly been more anxious to cross the Oregon state line, get to Bend, and walk into our new home — which we’d only seen pictures of online.


Fun Fact:

One of the first things I learned about our Oregon area was that it was where lots of the Disney 90s movie Homeward Bound was filmed. Remember when Sassy goes over the waterfall? That was an hour nearby, at one of my favorite dayhike spots: Sahalie & Koosah Falls.

Remember the scene where Chance & Shadow outsmart the mountain lion? Yep, that was shot around Bend! I recognized Smith Rock State Park right away.


At this point in our Oregon Trail cross country journey we hadn’t had any of our supplies stolen, gotten sick, injured, or had to restrict ourselves to “meager rations and a strenuous pace”. . .

. . . or by more realistic 2018 standards: we hadn’t gotten into a huge fight and wanted to kill each other. . . or run out of gas somewhere in middle-of-nowhere-B.F.E. . .

. . .or broken an axle (that one actually still applies).

We were at that final homestretch where you have to float the wagon down The Dalles river until you make it to the end!

(Again, if you haven’t played Oregon Trail, really you should go find the online version as soon as you finish reading this because I probably sound like I’m talking nonsense.)

We made it as the sun was setting. It was hazy from the wildfires even though they were burning hundreds of miles away, and hung like a burning, fuzzy, red orb. Bend was in the middle of a heat wave, too, and it was about 100 degrees outside; though us both being from the South where humidity is King - we thought it felt wonderful.

We threw whatever precious and essential supplies we’d stuffed the car with (kitty included) inside, then put our shoes on to walk. We were in love immediately, and we still are. Our first few days were spent exploring around town and getting settled in our new home.


Central Oregon is seriously magical.

There are mountains with peaks so tall they keep a little snow year round. rivers, streams, + alpine lakes created by volcano eruptions; rocky canyon valleys, deep dark forests + tumbling waterfalls that lay just on the outskirts of the desert nearby.

There is no shortage of adventure around every corner.

The cross country trail that led us here became our very own Oregon Trail, and it will forever hold a place in my heart. Just as special as that 90s video game, my Oregon Trail led me to this new adventure that’s unfolding right now in Bend —

-And thankfully thus far, there’s not a trace of dysentery.

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Photo by Alex Wolfe on Unsplash

Photo by Alex Wolfe on Unsplash

Smith Rock, just outside our little town of Bend Oregon. Photo by Jeff Finley on Unsplash

Smith Rock, just outside our little town of Bend Oregon. Photo by Jeff Finley on Unsplash


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