Skip to content

Oregon Trail of tears

April 19, 2010

I love Lacey. Like Lucy, but gayer.

Now you know that I have lost two great loves to a city I hate: Portland, Oregon.

In response to the last post about my loathing of hiking, camping and nature, Love No. 2 Lacey sent me an e-card from that unequivocally declared her aversion to extreme outdoor activities. As if I needed more proof she’s the perfect woman. You don’t deserve her, Portland. Treat her right.

Despite Portland’s documented, rampant and unconscionable cock-blocking, it dawned on me its state has been good to me in one way: the “Oregon Trail” computer game for Apple II.

As a child of the ’80s, I have such fond memories of playing “Oregon Trail,” from fourth grade on up. In my tween years, I’d name the folks in my Conestoga wagon after family members and our Lhasa apso, Delilah. It was a major letdown when my brother, Toby, wouldn’t perish from measles, typhoid or cholera. As a teen, my wagon party would include boys I had crushes on, and I’d cheer for Jimmy when his broken leg healed and mourn for Drew when he met his untimely demise by snakebite. Faced with five excruciating months of unemployment after moving to Boston in 2005, I rediscovered my love of the game, except this time my fellow trailblazers took the names of the four cats in our household – Isabel, Teva, Nina and Edward – who were home with me while my then-girlfriend Vicky (aka Love No. 1 pilfered by Portland) was at work. I credit “Oregon Trail” and staying in bed until 3 p.m. every day the support of my ex for getting me through that rocky road of joblessness.

"Oregon Trail" FAIL.

For old time’s sake, I thought I’d pop in the game on Saturday night (I know), name a travel companion after Portland and others who’ve wronged me, starve her with meager portions, subject her to a grueling pace and then revel in the death by drowning or dysentery of the double-crossing, sporty, Shamu-sized skankface. Except the disc from five-plus years ago wasn’t compatible with OSX. And then I discovered there’s an iPhone app, but the cutesy animation looked like an episode of “DuckTales.” Finally, I found the game online here, but the plug-in wouldn’t work. And really, you’d think by now I would have grown accustomed to the feeling of soul-crushing defeat courtesy of Oregon. And yet it still stings.

However, as the age-old saying goes, when Oregon hands you lemons, make trail mix. So I rooted around on the interweb, found screen shots from the three-decade-old game and altered them accordingly to exact my revenge. Portland, you may have Vicky and Lacey, but I have Photoshop and *a lot* of time on my hands.

And so it begins:

(If you’re wondering why younger/hotter Ellen DeGeneres is probably a vampire, go here.)

19 Comments leave one →
  1. April 19, 2010 2:57 PM

    That was AWESOME!!! I LOVED Oregon Trail – I remember playing on a computer that must have come from the USSR’s discard bin – it only typed out questions and answers, no images that I recall. But man, we played that fucker for HOURS in elementary school.

    Also, I don’t even like nature enough to enjoy patios. Those fucking mosquitoes use me as their personal buffet.

    Well done. I’m really glad you are blogging.

  2. Melanie permalink
    April 19, 2010 5:27 PM

    Really Jess? This whole elaborate setup just to get me to comment? OK, you got me. Not only have you gotten my attention, but I’m scared. Very, very scared. It’s not really a great time for me to do an intervention on you right now, but dammit, that’s what friends are fer. Circle the wagon, as it were. Not that you’re as big as a wagon or anything.

  3. alexandria permalink
    April 19, 2010 6:25 PM

    were this facebook, i’d be clicking “like.” since it’s not, i’ll just ask: how do we make this go viral?

    • April 20, 2010 1:11 AM

      Hmm. That’s a toughie. Maybe send the link to everyone you know? And ask them to do the same? And then you’ll all be my puppets in my lightning-fast ascent to world domination.
      Just kidding. You guys aren’t my puppets. Puppets are scary. You’re my monkeys.

  4. April 19, 2010 6:47 PM

    I love every word.

  5. MirtoP permalink
    April 19, 2010 7:04 PM

    Coincidentally, one of my favorite bloggers, super-cool opera singer Jennifer Rivera (, just happens to be in Portland (yes!) rehearsing for performances of “The Barber of Seville,” where she video-blogged “A day in (her) life”: She seems to be having a good time out there (see???), biking to work along the river, etc. Not that there’s anything wrong with that…

  6. April 20, 2010 3:47 AM

    I think that the best way to world domination is via old video game illustration.

  7. The General (aka: Mommy) permalink
    April 20, 2010 11:18 AM

    Oh, I too have memories of Oregon Trail in elementary school. Anyone remember the big boxes we had to insert the floppy disk into, not to mention the itty bitty black screens and green type!!

    My trailmates were named Travis(school crush), Daniel (first kiss), and Amy (best friend) amongst others. I mourned every time poor Travis, who was uber popular and never even spoke to me, was crushed by the wagon or starved to death. My future self realises now that he totally deserved it though, right? I should’ve named every character after him to inflict maximum punishment. Because that’s not at all weird and creepy.

    As an aside- Disney Fairy! lmao

  8. The Bad Lady permalink
    April 20, 2010 11:20 AM

    I have no words, Jess. That was awesome. Completely, utterly, unequivocably AWESOME.

  9. The Bad Lady permalink
    April 20, 2010 11:23 AM

    Unequivocally is what I meant to say. And yes, I’m a writer. But apparently, a really, really terrible one. Just ask my editor.

    • April 20, 2010 1:29 PM

      I must be a terrible writer, too. Because I originally wrote “unequivocably,” and kept cursing spell check for marking it wrong. Whatever, spell check. It should totally be a word. And at least one person agrees with me. Boo-ya.

  10. meredith permalink
    April 20, 2010 1:48 PM

    ‘make it go viral,’ you say? ON IT.

  11. April 20, 2010 4:07 PM

    I totally remember Oregon Trail! Ah the joys of floppy disks and games bogged down by text not hyperrealistic graphics. I love the modern update, it was freakin’ hilarious. I especially love that George W keeps pronouncing dysentery as Disney Fairy, ha. I’m all over the ‘making this viral’ campaign.

  12. April 20, 2010 5:16 PM

    I always tried to take really good care of my Oregon Trail party on Apple II E, unlike many people who just wanted to go at a “grueling” pace and eat “meager” fare. I was so devastated when anyone died that I’d just quit and start over. And that’s how I’ve wasted so much of my life.

  13. April 21, 2010 11:41 PM

    I’m from Texas so I’m pretty sure the game was banned. Texans don’t like to think about the other states that “might” exist in the US (we haven’t confirmed their actual existence as of yet). I can’t speak to Marie the creepy stalker but it was a pretty realistic portrayal of Dubya and vampire Ellen, kudos to your photoshopping skills!! Plus I laughed so hard I peed a little.

  14. April 27, 2010 2:15 PM

    How much do I love Oregon Trail? So much that I”m not going to try that link yet – I need to mentally prepare if the plug-in fails. I spent MANY a computer lab laughing as I accidentally drowned cheerleaders (and other unpleasant things) during a river forging. And how much do I love blogs that involve Oregon Trail? Ineffably much, THAT is how much.

  15. redg_rl permalink
    May 17, 2010 10:12 PM

    aww.. the first computer game i fell for.. or maybe the only computer game? nintendo had more action but it was fun when folks would die out on the trail

    there’s a website where you can play the original version but it has a tendency to freeze at times & that’s quite disappointing.. particularly if nobody’s died yet.

    hooray for gwb drowning!

  16. July 7, 2011 8:30 PM

    I just re-read this and I think it’s one of your funniest and most creative posts to date. You made me laugh all over again. Just thought you should know.


  1. Oregon Trail of tears « alone … with cats Lamar university

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: