26 at 26: O for Oregon Trail

A Cross-Country Story


Late last year, I turned 26. So, in the tradition of the great panel show QI, for the first half of 2014 I will be running through an alphabetical view on 26 things in my world so far.

On Sept. 26, 2012, I posted a thread on NeoGAF. It was my first public confession of a steadily-growing desire: I, a girl who had never left the Eastern time zone, wanted to go west.

Six months later, March 6, I landed at PDX. In heavy rainfall.

I still applaud the city for being so honest, right from the get-go.

I didn’t move to Portland that day. I’d like to think I’m a pragmatic girl, or at least one not so crazy as to cross the nation on a whim and a prayer. My visit actually included a job interview and a few looks at apartments that I managed to coordinate remotely. I wasn’t a tourist; I was a scout.

And I was in love. A frightened, nervous love, but by the time the Red Line dropped me back at the airport I knew my mind was made up. I had considered Seattle, San Francisco, Austin, the lot. Portland won.

About two months later, I hesitantly accepted a job offer and gave my two weeks. And since you only get one youth, I was going to become an Oregon girl by way of The Great American Road Trip.

Woefully unprepared for what I was doing, I packed up my New York life. I spent far too much money sorting out logistics. Friends visited to help pack crates and say goodbyes. Family, for various reasons, refused to.

The last visitor was my old friend, Sydney. I had proposed that she join me on my cross-country drive, and she agreed. We spent my last night in New York at a quaint hotel right off I-90, and on May 20th, we drove off.

Day 1

Sydney and I knew each other for years. But, we hadn’t spent much time so near each other. Not so much in each other’s company, but in a Ford Fiesta. It’s a small car. I fully expected we’d snap by Mountain Time.

But the trip was young, and we had our energy. We made it through New York and the Erie chimney of Pennsylvania without any fuss. The weather was kind, the company was good, the roads were clear.

Spirits were, therefore, high. We laughed at what we were doing and had inane little conversations about random girl-geek things. We were happy to be on the road.


I had planned this trip meticulously. I knew that we’d arrive in Cleveland for lunch, and sure enough we managed to just beat the rush at a downtown sandwich shop. It nicely fit one of the Road Trip Rules: never eat what you could eat at home.

Downtown Cleveland felt like a real, proper downtown. I wasn’t exactly used to it, having mostly lived in suburbs, but it was nice. Nothing exceptional, but nice.


To maintain the timing, and to give us a break from sitting in a car for hours on end, I took Sydney to the Rock and Roll Hall of Fame.

I’ve been to the Hall once before, many years ago (maybe a decade or so). It’s about how I remember it, but it was good to see it all again. And good to see a bit more hip-hop representation.

We talked about how the future history will look in the Hall; exhibits on MySpace and Soundcloud and the whole digital landscape. I was left wondering, in a world where the Internet offers every and any kind of music to anyone, would there even be rock stars like what the Hall immortalizes. It feels like there’s less of a reason to care these days, and less cohesive and emergent movements.

I also had my gusto for performance reignited. It’s hard not to wanna rock out after you’ve immersed yourself.


We rested outside South Bend, Indiana. Because of our I-90 approach, what we saw of the area was mostly Wal-Marts and strip malls, the sort of neighborhoods I sought to avoid. We passed up dipping into Michigan and instead, after dinner at Culver’s, got to resting. Driving a car all day, it turns out, is pretty exhausting. And there were five more days of it.

Day 2

My grand planning meant that Day 2 needed to get rolling nice and early. The reason: Chicago. We’d be crossing into Central time on the way, but even so, rush hour was to be avoided.

Sunrise over Mishawaka, IN

In avoiding both high traffic and toll roads, we snaked through South Bend and neighboring Mishawaka. Beautiful towns, much more visually interesting than what we encountered the night before. I felt bad for writing the area off entirely.

The snaking through Chicago was less endearing. Something about driving rather slowly through neglected ghettos with all your life’s possessions in the back of a hatchback is, it turns out, unsettling.

Ultimately, the detours weren’t actually saving time, and so they were abandoned.

First bit of planning gone awry.

Next bit was in visiting a friend near Sheboygan, the second-most amusing town name in our trip. We had planned on a lunch spot, only to find it closed. We wound up chatting music in a pizza buffet place. Turns out, the three of us share almost no tastes in music.

Third bit to go awry: what to do with our padded afternoon. The weather wouldn’t allow for mini-golf, and the midwest is slightly lacking in other distractions. So after several awkward fits of shrugging, we played Rock Band for a little while (I know the friend through the Rock Band Network) and called it a send-off to a series that had ended the month before.


Amid the day’s confusion and my slowly-worsening shoulder, the in-car chats got a little more serious. Somewhere in Wisconsin (the state seems to drag on for ages), Sydney confessed that she didn’t want to go back to New York.

I couldn’t blame her. We had gone 900 miles, put three Great Lakes between us and our hometowns. Neighborhoods rural, urban, and suburban were all still familiar, but with more and more new names showing up. We were going through change, exploring physically and metaphorically. It’s confusing and disappointing at times, but that doesn’t make it a bad experience.

Day 3

Next destination was Minneapolis/St. Paul. Getting there from Wausau, WI meant hours of country highways, the most rural of our drive yet. The sort of roads that only bend for the curvature of the Earth.

We were so bored, Sydney and I let our minds wander into absurd associations and topics just to provide some matter of stimuli. Red Bull proved ineffective. I don’t know how truckers do it.


We eventually made it to the Mall of America. Sure, it’s a blatant tourist destination, but the trip is all about doing things big and that’s what Mall of America is about.

But it wasn’t actually that interesting. It’s huge, but it’s all stacked on itself, so it doesn’t really feel that big. King of Prussia felt bigger. Plus, we didn’t go into the whole theme park in the middle (although, I admit, it was a bit of a sight). The Mall is huge, but only in the context of malls, which themselves are relatively small. We had broken the 1,000 mile mark by that point; a single building was never going to feel huge in comparison.

Lunch was food-court food, because it’s a mall. That’s what you do. Sure, there were approximately a thousand sit-down restaurants there, but it’s a mall so you eat mall food.


We left in drizzle. More gray, more straight roads, more lack of stimulation. By the time we stopped in Mitchell, South Dakota, I was virtually asleep.

Our dinner that night was the first time I felt really out of place. Sydney and I make a slightly odd pair; we obviously belong more in the city. And there we were, in a truck stop restaurant. The kind that serves chicken-fried steak that tastes like KFC and pours drinks in mason jars with no sense of ironic kitsch.

It was the halfway point — 1,550 miles. Middle of America. I had never been so far from my comfort zone. I was scared, tired, sore, and enjoying it.

Day 4

I thought Wisconsin was boring until I drove South Dakota. The state is so flat, it feels like the horizon is missing. There’s just nothing there.

Until the Missoula River. Writers should have to drive that stretch so they can experience a proper buildup and tension release. It’s just a river, but the dip towards it after hours upon hours of perfect flatness feels glorious.

If you’re crossing South Dakota, you pretty much have to hit Mount Rushmore. So we did. The buildup there is also pretty nice. Not only are there some surprisingly nice tourist towns at its base, it’s more than just faces in a mountain and that’s it. There’s a whole monument behind it, with an aisle of state flags leading up to the display. We stopped and smiled at the Oregon state flag, tangled up on its pole. It would be mine soon, we noted.

But for now, we had to snake back down the Black Hills (in a driving experience that felt out of Top Gear) and make our way to Wyoming. Where, no word of lie, tumbleweeds kept crossing our path.

Sheridan, Wyoming

Eventually, our path crossed Sheridan, WY. The winds were intense, so we rushed into the rest stop to gather ourselves.

Four days of driving were starting to really take their toll on my shoulder. At 625 miles, it was the longest single day of the entire trip. It was painful and tiring.

I did the math, based on past conversations. Sydney had never been further from home than that moment. I had been, but flying doesn’t have the same impact, the same intense sense of scale.

The reality of the whole thing hit us, and hard. We lived our lives near the Appalachian Mountains; now we were looking out at the Rocky Mountains. We had gone so far that the Fiesta’s trip meter, which maxes at 2,000 miles, rolled over. Neither of us had ever done anything even vaguely resembling this. The sheer scale was overwhelming.

We stood in that rest stop, alone save for an elderly couple in the other wing, and cried on each other’s shoulders, smiling.

Day 5

Montana and Idaho are actually interesting to drive through. Lots of mountains and winding roads. I was powering through the shoulder pain and foggy downpours like a woman on a mission. Maybe a part of me wanted to “butch up” after yesterday’s show of emotion or something.

Butte surprised me. Not because it was small — we had spent the night in a town with seemingly no traffic lights — but because, for whatever reason, it felt almost endearingly small. As in, the whole city was one tight-knit community that just knew each other so well. They worked together, they went to church together, they ate together. The pizza place we hit for lunch was packed, stuffed with residents socializing with each other and the owners. I could never live in Butte, but it had a positive character.

Even though folks were generally friendly all the way along, that was the first time I really noticed that small-town kindness. I never had to ask for directions (GPS and aggressive planning saved the day), but I had the feeling that everyone there would’ve been happy to point us the right way to Spokane.

The road to Spokane reminded me of my time living in northeast Pennsylvania. That was when I was really living among mountains, and the route was reminiscent of those highways. Roads were probably better than in PA, but after thousands of miles, we were starting to get somewhere that actually felt kind of familiar. Even the occasional industrial neighborhood sliced by the highway felt like areas in Hazleton.


View from Hotel Ruby, Spokane WA

Speaking of Pennsylvania — Spokane felt like Scranton. Bobby Roberts, a podcaster that Sydney’s a big fan of, calls the place “Spo-Compton”. It’s a city, worth putting on a map, but it gave the impression that its best years were and may always be behind it.

But damned if it’s not trying, at least. We stayed in a cheap yet trendy hotel that I could probably claim was somewhere in Portland or Austin. We went to dinner at a mall that seemed to be recovered from some past industrial life. There were recognizable chains with urban-styled locations. I don’t know that Spokane will be successful, but at least it’s not wallowing.

Day 6

When you’re afforded the chance to go to Walla Walla, Washington, you go. Not because it’s a great city — there’s a nice small-town-feel main street but not much else. No, you go because that name will never stop being funny. That’s why we went.

Eastern Washington (and Oregon) is mostly farms, but it’s also mostly hilly and swerving. A lot of spots that look like Bliss. A good place to talk about how much we appreciated each other; in my case, for the company on such a massive undertaking; in Sydney’s case, for showing her an experience she never expected to have.

We cried a little on Route 730, as we passed the sign: “Welcome to Oregon”. We were home.


The following day was filled with spats of tourism, visiting the Tardis Room and the Japanese Gardens and the like. Sydney flew back to New York the day after, after a great deal of begging to stay. The moment she returned, her job hunt became aggressive; it’d be a few more months before she could make the return flight and become a fellow Portlander.

I know we were both interested in moving here long before the whole drive happened. We had different reasons, different things we wanted out of the city, but we both had the desire. Yet I can’t help but feel like extending that invitation made her want to move.

Perhaps it’s just the manifestation of knowing that, between the long miles and spotty restaurants and Foo Fighters sing-alongs and rest stops and tourist traps and unfamiliar hotels… it changed her life.

It changed both of our lives.

And now, a moment of zen:

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