There is today, a today where computers are not only everywhere, but borderline mandatory. And today, these computers are capable of amazing things. Things like Facebook and watching Netflix and designing Power Point presentations and watching YouTube. These computers I’m assuming have games on them, or the ability to have games loaded onto them. I only say assume because I don’t play computer games. I don’t consider taking a Buzzfeed quiz to determine which character from Dazed and Confused I am a game. I consider it informative and potentially life-changing.

Although I got Slater. That seems outdated to me.

Now speaking of outdated, back when I was youngster, parting my hair on the right, looking adorable, hiding my feet that were growing too fast, we had computers in school- tan and boxy. The screen was green. For the most part their main function seemed to be typing. That’s it. They were typewriters with screens. The cursor blinked. Did I mention the screen was green? It was. Didn’t matter what you were doing. The screen was green. Typing, doing math or even better, playing Oregon Trail, the screen was green. And yes, Oregon Trail. It was the computer game for a little while there. It was what you played as a treat because quite honestly, you didn’t know what else to do with the computer. Somehow this constituted computer training, but possibly even working on your life skills. Which I suppose made sense, even though I was living in Maine and wasn’t even 100% positive sure oxen were a real thing.

I can’t stress this enough, Oregon Trail was a big deal.

And then it was gone. Computers kept getting better, more prevalent, more functional and with these changes, Oregon Trail became more and more antiquated. It became something that was reminisced about, but never played. Just another childhood memory, like TGIF and Mountain Dew. It was something that you couldn’t imagine ever coming back into your life.

Well that is until someone on the Internet brought Oregon Trail, as well as other games of that era, back into our lives.

I couldn’t resist playing. Just once. Just for kicks. Just to get to Oregon with my family in tow.

The first thing you do is pick where you’re from and what you do.

You have three options:

I chose banker from Boston because I wanted to make this as real as possible. And no, I have never once considered being a banker, but I’ve been to a bank and on more than one occasion considered moving to Boston.

Would this hurt my chances of success, though? Wouldn’t a farmer or carpenter, either one from more rustic areas of the country, have a better chance of making it from one end of the trail to the other? Yeah probably. Definitely a better chance than some east coast, white collared liberal. But banker from Boston was a choice that came from the gut so banker from Boston it is. I imagine I’ll regret the choice, but it’ll probably be because I’ll have so much time to think about things while riding the trail. No second-guessing! Banker from Boston it is.

Next up you load up your wagon with your family. I really thought about this; much more so than the banker from Boston thing. I really wanted a good crew, something that is always essential when planning a trip.

Giddy Up America’s Oregon Trail Wagon

Tom Brady
Rihanna
Dave Grohl
Questlove

Why those fine people? I’ll tell you.

Tom Brady: steady, reliable, pancake master
Rihanna: unpredictable, sassy, “relaxation expert”
Dave Grohl: jokester, in charge of campfire singalongs, story teller
Questlove: wagon DJ, lots of friends & connections (for trading purposes)

We were ready to roll. And we were going to roll in April. They give you options of when to leave. April seemed to make sense. I think. I am a banker from Boston, so this might not be in my wheelhouse. I’d ask my crew but ol’ Tommy Blue Eyes is texting Gisele about God knows what, RiRi is already onto her second blunt, Quest is consumed with picking the right music for the trip and Dave is rambling on about the unheralded music scene in Independence, Missouri. So the decision is mine. The decision is April.

Before leaving we stop at Matt’s General Store for supplies. We have $1,600 to spend.

Matt recommends 3 Oxen yoke (2 oxen per yoke.) We get 4 yoke.
Matt recommends 200 pounds of food per person. We get 1,000 pounds and pledge to ration properly, even RiRi, who you know…munchies.
Matt recommends 2 set of clothes per person. We get 14 sets, giving us a few extra. Seems smart.
Matt has no recommendation for ammo. We get 15 boxes. This makes sense to Dave. I’m sold.
Matt recommends “a few spare parts,” which consists of wagon wheels, wagon axles, and whatever the hell a wagon tongue is. We get two of each and no proper explanation about what a wagon tongue is.

Sadly Matt does not carry rolling papers, Afro picks, Jack Daniel’s or Uggs. Our crew is set, but not 100% satisfied.

It’s March 1, 1848 and we’re off. Peace out Independence. Next stop Oregon.

Actually, next stop is 19 miles in as one oxen is already injured. Damn it Matt! Never trust the only store in town! And then, only a few days later, seven exactly, we run into a blizzard and lose a day. Needless to say, we are not off to a good start. Crew is in good spirits, though. Questlove’s music choices are predictably on point and Dave is handling most of the driving with Brady on map duties. Ri Ri? Snoozing. But looking super fly while doing so.

Rivers:
Kansas River: we “attempt to ford” i.e. cross carefully and are successful.
Big Blue River: we “caulk the wagon” i.e. float across and are successful.

We got rivers down pat. Good feelings are fleeting, though. This is meant to be ominous.

March 18: severe blizzard.

March 21: Questlove gets cholera. Ri Ri wisely asks him to put together some playlists because you know, in case he…well…we don’t want to talk too much about it…but in case he dies.

March 23: Which he does.

Tom, the ultimate team player, vows to rock a hair pick for the rest of the trip as a tribute. God, if we lose Tom…

March 26: Tom Brady has exhaustion. NOOOOOOOOO!!!!

March 28: Tragedy.

Two deaths in a week. Our crew is understandably rocked. We spend the night of the 28th mourning our fallen travelers with shots of whiskey, Ri Ri’s special “emergencies only” stash and tales of Questo’s and Brady’s greatness. It is a night interlaced with sadness and fond memories. We pledge to go on, we pledge to never forget our friends.

On a happier note, I’m getting better at hunting.

Unfortunately I could only carry 100 pounds back, which is kind of a bummer. Tom Brady’s loss is felt. He could carry back at least twice that. Damn it, Tom! Why did you have to die? The good ones always go too soon. Sleep well sweet prince and please beat the Ravens this weekend.

It’s just Dave Grohl, Rihanna and me now. We must continue on. It’s what Questlove and Tommy Football would have wanted, what they dreamed about.

For the next few weeks things are quiet. It gives us time to think. Why are we going to Oregon anyway? Jobs, food, family? If we’re going cross country, shouldn’t it be to some place like San Diego or L.A.? I’m not sure Oregon makes much sense. San Diego is sweet. I wonder if we really thought this through. We probably didn’t. That’s so like us.

Then a rough two week stretch hits.

We told her to be mindful of where she wanders off too. But you know, stoners.

May 3: Good day for hunting, but bad day for navigating. We lose the trail. I mean, it’s not like there’s many other trails. There’s really only the one. But we still lost it. I’m not going to point fingers at anyone. But…when Dave Grohl assures that he knows how to read a map, you believe him. It’s Dave Grohl, the guy who wrote “Everlong.” That’s an awesome song. Dude who wrote that mustknow how to read a map. Right?

Dave is off map duty. And on top of that, our food rations are running dangerously low because someone (no names, only initials: Rihanna) is constantly snacking for reasons that…well, you know (in a whisper: weed.) We are forced to make a shift in our rationing policy, changing from filling to meager.

May 12: Ri Ri has the measles! No, not Ri Ri! She’s our heart & soul!

May 13: She was our heart & soul.

We take a day off. We need to. This latest death has really shaken us. Ri Ri was going to bring the people of Oregon wonderful recipes from Barbados. Now? Now there will be no Barbados-inspired restaurants in Oregon. It is a sad day in Independence Rock. Dave is inconsolable. Rumors about some late night hook ups with Ri Ri might have been true. I didn’t believe them, didn’t want too. But for how shaken up he is? Kind of, sort of seems like something was going on. Oh well. What happens on the Oregon Trail stays on the Oregon Trail.

While Dave drowns his sorrows in more whiskey…how much did he bring?…I visit with my Aunt Rebecca and trade for some supplies. We need clothes. I have no idea where our clothes went, but we’re running low and Dave and I look ridiculous. He’s wearing one of Ri Ri’s shirts, I’m wearing most of Questlove’s old clothes and they are comically too large for me. Honestly, we look like assholes.

This concern about appearances would be short-lived.

May 16: Dave has measles. Which is you know, kind of weird because our girl Ri Ri had measles too. Are measles contagious? What are measles? Are they like chicken pox? Damn it. Questlove would totally know the answers to these questions.

May 18 is a rough day.

So that leaves just me.

Everyone else is dead. Questlove is dead. Tom Brady is dead. Our beloved Rihanna is dead. Dave Grohl is dead. It feels like the dream of Oregon is almost dead. It’s on life-support.

May 21: I have cholera.

What the hell is cholera!

Cholera: Cholera is an acute intestinal infection caused by ingestion of food or water contaminated with the bacterium Vibrio cholerae. It has a short incubation period, from less than one day to five days, and produces an enterotoxin that causes a copious, painless, watery diarrhoea that can quickly lead to severe dehydration and death if treatment is not promptly given. Vomiting also occurs in most patients. – World Health Organization

Well that sucks.

So does breaking an arm.

And then having dysentery.

I’m having a rough week. Perhaps I should have stayed in Boston doing that banker thing. Ever heard of a banker getting cholera? Getting dysentery? Burying his friend Questlove? I haven’t. It’s quite possible that I’ve made a huge mistake.

June gets off to a rough start.

Damn it, another effin’ wheel! I spend the day trying to trade for a wheel, having to surrender a set of clothes (Dave’s) to get the wheel.

June 28: I have a fever.

Yes, it’s called loneliness.

July 10: Damn it, lost another wheel. I should have read reviews of Matt’s General Store! His wheels are shit.

The bad luck doesn’t last all that long though. Two weeks later I come across an abandoned wagon. Finders keepers on the trail, bitches! My looting “salvaging” gets me some more bullets and clothes. Maybe this is a sign? Maybe things are starting to take a turn for the best and things are starting to look up and my luck is starting to change?

Maybe I’ll make it to Oregon after all?

August 3: I have a broken leg.

August 11: I have (another) broken arm.

August 12: I have measles.

August 20: I’m dead.

I made it a little over halfway to Oregon. And then the game made fun of me.

See you in another twenty years Oregon Trail.

Ryan O'Connell loves the Boston Red Sox, New England Patriots, the Black Keys, the Roots, his family, The Wire & the writing of Dave Eggers although his last couple books have been “meh” at best. He does not care for waiting, appreciates someone who maintains a nice front lawn, and harbors a constant fear of losing his keys. See more of his writing at his website, GiddyUpAmerica.com