Oregon Trail: 21st Century Edition Part 1

When I first found out I was moving to Oregon, it almost didn’t feel real.  It was a few days before my flight to Santiago, I had just quit my job, I had this epic adventure before me, and I just couldn’t wrap my head around it.  But a few weeks later I found myself in a hostel in Cusco, searching online for a temporary place to live in Portland and trying to plan a cross-country road trip to get there.  I think that’s when it dawned on me: I would be loading up my belongings into a vehicle and traveling across the country to start a new life.  Maybe someone else would have experienced something profound upon this realization, but for me I just thought of the Oregon Trail.

Windmills in Iowa- a new addition to the Oregon Trail

I loved the Oregon Trail game.  I can remember gathering around the lone computer (one of those old, boxy Apple models) in the back of an elementary school classroom during winter recesses and watching a pixelated covered wagon move along a map before a pop-up box alerted that someone had died of dysentery.  Maybe it sounds odd and kind of boring, but I loved that game enough that my parents bought me a version for our home computer.  That version was an update- it had better graphics and more route options but the object of the game was the same: get your little computer family to Oregon without anyone dying of dysentery (or cholera, or starvation, or hypothermia…).  As I sat in Cusco feeling nostalgic about a computer game from my childhood, I couldn’t help but feel that my obsession with a game as a child had almost predicted my own fate twenty years into the future.

Cupola spotting


As I started route-planning that day, I really wanted to follow the actual Oregon Trail as much as possible.  I thought it would be exciting to follow a trail that early settlers had carved out almost 200 years before, a trail that had inspired a game I played as a child.  I did some quick research on the trail history and started plotting points on a map.  However, I soon realized that following the actual trail wouldn’t be possible for me.  Based on my own travel schedule and the start date at my new job I only had a week at most to get from Pittsburgh to Portland, and just to get to the trail’s main starting point in Independence, Missouri meant driving considerably out of the way.  This was a bit of a disappointment (though not enough for me to cut my South American trip short), but I resolved to at least attempt to see some of the same sites along the way.  And then only a few short weeks later, my mom and I were standing in my parents’ driveway next to a packed car, ready to embark on our own version of the Oregon Trail.

Players:  Me and my mother

Wagon Model: Subaru Crosstrek

Supplies: The necessities: an air mattress, clothes, a French press, a waffle iron, books, and a few other odds and ends.  (I should note here that I had more belongings packed in a storage facility.  What I was bringing “on the trail” was intended to last me 3 – 4 months until I found a permanent apartment in Portland).

Starting point: Pittsburgh, Pennsylvania

Ending point: Portland, Oregon

Distance: 2,600 miles


Day 1: Pittsburgh, PA to Chicago, IL Bolingbrook, IL (516 miles)

Our journey started out very simple.  About a half hour into our multi-day trip my mom and I figured out that she preferred to drive and I preferred to navigate, so we switched spots and continued out of Pennsylvania and into Ohio.  We had taken a few family vacations to Cedar Point when I was younger, so the first couple of hours were in familiar territory.  If you’ve ever traveled I-80 in Ohio then you know there’s not much to look at, but I tried to keep us entertained.  I played a few random playlists on Spotify, doing my best to satisfy both mine and my mom’s tastes.  I had my iPad with me, and there were a few books loaded on my kindle app and I also had a few games downloaded.  We stopped at two rest stops in Ohio and had a Groundhog Day moment at the second.  The buildings looked exactly the same on the outside, we parked in the same space, and the inside had the same setup as the first.

One of Ohio’s lovely rest stops

Eventually we crossed the state border into Indiana, which I expected to be exciting.  It was a new state for both of us, and I was happy to check another state off my list.  As it turns out, Indiana is not that different from Ohio (at least along I-80).  The only major difference we discovered was that Ohio rest stops are better than Indiana rest stops.  We passed the time by pointing out cupolas on barns in view from the highway (I had to google what they were and why they existed).  And then we crossed into Illinois, where things got as interesting as they would on our first day.

I had plugged Chicago into my GPS with the plan to stay in or near the city for our first night.  I was entertaining thoughts of exploring the city for an hour or so before settling in for the night.  However, after crossing the state border (and a very large bridge) and nearing the city itself, my mom realized what was going on and announced that she didn’t want to stay in the city.  I conceded that this made sense considering how expensive downtown hotels are, so after getting off and back on the highway we ended up in Bolingbrook, IL.  It wasn’t the downtown experience I had expected, but the hotel bar had local craft beers on tap so I was satisfied.

Almost into Chicago

Day 2: Bolingbrook, IL to Seward, NE (524 miles)

On our second morning we had an amazing breakfast at the hotel before starting out.  We met up again with I-80 after our almost-Chicago detour and continued west through Illinois.  Fun fact: along I-80, Illinois is not that different from Indiana (and Ohio).  We continued to amuse ourselves by pointing out cupolas, but even that was losing its appeal.  As the day (and road) dragged on we began to look forward to the next big event on our Oregon Trail experience: crossing the Mississippi River.  Not only was I able to make a joke about “fording” the river, but this also meant moving on to another state- Iowa.

Crossing the Mississippi River is a bit easier in this century

To be honest, I didn’t have a very high opinion of Iowa before our journey.  This is most likely because the only times I ever hear anything about Iowa are during the Iowa State Fair and the Iowa Caucus.  I dislike the caucus because politics in the US suck right now and as for the state fair it’s my opinion that some foods shouldn’t be fried.  Anyway, after spending about 5 hours driving across Iowa on our trip, I’m sad to say my opinion of the state hasn’t really changed.  I would honestly be satisfied if those were the only hours of my life spent in Iowa.  First, my mom and I encountered a chain of gas stations called Kum & Go.  Seriously!  Can it get more sexually explicit than that?!  Granted, these stores weren’t only in Iowa but it seemed like they were the most popular gas station there.  I was not impressed.  Then I suffered a hallucination in Iowa due to extreme boredom, something my Oregon Trail game experiences hadn’t prepared me for.  Cholera, dysentery, okay- but hallucinations?  Nope!  As we were driving, I looked out my window and way off in the distance I saw a series of structures along the horizon.  The following conversation ensued:

Me: “Mom, look, there’s a city over there.  I wonder which one.  Maybe Des Moines?”  (I proceed to consult a map).

Mom: “I don’t see anything.”

Me: “Look, over there!”  (Mom looks again).

Mom: “I think that’s just a bunch of trees.”

Me:  Silent disappointment.

Iowa’s one redeeming quality were giant windmills.  We passed many of them, and one of the rest stops had a lot of information about them and how much power they can generate.  Reading about windmills was easily my favorite part of the day.

At the base of a giant windmill

Needless to say, I was quite happy when we made it into Nebraska and passed Omaha.  It was a city!  There were signs of life!  There were actual buildings in sight that were not trees disguised as skyscrapers!  Once we made it to this point, we began to look for a place to stop for the night.  We got off I-80 at a town called Seward, which turned out to be a treat.  Seward, Nebraska is the Official 4th of July City in America- something we would have never learned without stopping there!  I was pleasantly surprised to learn this fact and enjoyed spending the night there.  Seward was a good end to a relatively boring day, and it marked the beginning of our adventures in Nebraska.


Two days into our journey, we weren’t even at our halfway point and I was already suffering from boredom.  Obviously, I was not cut out for the pioneer lifestyle.  I was grateful that I was making the trip in a Subaru rather than a covered wagon, because I couldn’t imagine how people endured the journey for months on end without succumbing to boredom.  (They were probably too busy trying to stay alive, but that’s besides the point).  As we continued our trip would I continue to suffer from boredom?  Would I have any more hallucinations of civilization?  Would we ever arrive in Oregon?  Stay tuned for Part 2 of my Oregon Trail: Modern Edition experience!



3 thoughts on “Oregon Trail: 21st Century Edition Part 1

  1. East Coaster on the West Coast

    So just read your latest chapter to your blog, can you elaborate what exactly is a cupola for those who wants to know more about it? And which versions of the Oregon Trail did you play and did you ever made it with your entire virtual family?

    P.S: Still remember playing the 1990 and 1995 version on the iMac G3, those were the best in my opinion in term of gameplay, interface and depth. The Oregon Trail games are still one of the best game series ever…

    -East Coaster on the West Coast


    1. Stories from Someplace

      A cupola is a small tower-like structure on the roof of a barn- check out the second photo in the post! From my understanding, they are used for ventilation.

      I’m not sure which version of the game I played growing up. I wasn’t too concerned about those kinds of details as a child! I’m thinking I had “The Oregon Trail II” at home, and whatever I played in school would have been an earlier version of the game. I can’t remember if I ever made it with my entire virtual family, so I have a feeling that never happened…

      Liked by 1 person

  2. Pingback: Oregon Trail: 21st Edition Part 2 – Stories from Someplace

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