A few weeks ago, I tried to define what makes a board game the worst board game.

And I made a passing reference to The Oregon Trail Card Game and my work group’s Sisyphean efforts to conquer the game.

Some of the readers politely requested more details on that endeavor, so today, let’s look back on our repeated attempts to survive the Oregon Trail.

For those not in the know, The Oregon Trail was a computer game designed to explore 19th-century pioneer life on the long journey between Independence, Missouri, and Oregon’s Willamette Valley. Players would manage food, supplies, and the pace of the trek in their covered wagon, occasionally dealing with dangers like disease, thieves, broken equipment, accidents, and treacherous rivers to cross.

So when it made the jump from the digital realm to the analog one with a card-game version, I immediately snapped up a copy to play.

But my fellow travelers and I quickly discovered that the card game was harder than the computer game. I don’t know that I’ve ever encountered a game that stacks the deck against the player quite so brutally.

To make the journey to Oregon successfully, players must traverse 50 trail cards, avoiding illness and unpleasant twists of fate along the way (represented by the calamity cards that come up all too often), managing meager supplies, and testing their luck against river crossings (where a roll of the die determines your fate).

This quickly becomes a strategic battle of resource management, trying to hold onto fort and town cards for as long as possible (since they provide some of the rare opportunities to gain new supplies), playing trail cards (which must link up in a continuous line), and deciding whether it’s better to spend medicine and clean water supplies on saving fellow players stricken by illness or letting players die and hoarding supplies for the survivors.

Of course, we didn’t realize that going in, so on our first attempt, we only made it 40% of the way to Oregon before losing the entire traveling party.

(I died of Cholera, Measles, and drowning all at the same time. I am, if nothing else, an overachiever.)

On our second attempt a week later, we did slightly better, making it halfway to Oregon.

(I died of a rattlesnake bite on the very first turn of the game. Brutal!)

Our third attempt was far more promising, making it 80% of the way to Oregon, but being forced to stop because lunchtime was over. Two members of the party had died, and supplies were low, but we were making progress!

(I died of extreme cold. At least I keep switching up the deaths to avoid being repetitive!)

But by week four, the cards were on our side and our tactics were dialed in. The party made it to Oregon! Sure, our supplies were low and we lost three party members, but we had reached the promised land!

(I actually survived this time, but in my notes, I decided that, upon arrival, I drank myself to death in victory by accident.)

After our glorious victory, we took a break for a few months before trying our luck again. We also took another look at the rules and realized only a maximum of six players were allowed, and we had triumphed with seven players.

Our victory was invalid. WE HAD TO TRY AGAIN.

And the Oregon Trail was vengeful. We were one card away from our sole survivor making it to Oregon, the rest of the party having perished along the way. My notes state: “Lone survivor’s corpse coasted into Oregon at the last minute, drawn by loyal oxen. We’re calling it a win.”

(I died of Typhoid.)

The second attempt of the new year was our first true success. Two out of six players made it to Oregon! No asterisks in the win column this time.

(Since we could only have six players, I sat out this game… having been trampled to death by a runaway emu before boarding the wagon.)

It wasn’t until the next summer that we once again tried our luck on the unforgiving Oregon Trail.

Our first attempt resulted in a TPK, as we only made it 70% of the way to Oregon. There would be no back-to-back victories on this day.

(I died once again of a rattlesnake bite. I’m just too delicious, I guess.)

On our second attempt, we made it 85% of the way to Oregon before the party succumbed to accidents, ailments, and all manner of obstacles.

(I again sat this one out, having been gunned down in the street the night before our departure by the dreaded outlaw “Frosty” Wendy McSpicychicken. Can you guess what I had for lunch that day?)

Our third attempt was similarly disheartening, only making it 70% of the way to Oregon. This is when we truly realized that no matter how good your gameplay was, sometimes the cards simply aren’t in your favor.

(I died of extreme cold.)

Our fourth attempt was our closest yet, making it 90% of the way to Oregon. Despite a valiant final push by our two survivors, a ravenous river and one player’s on-again, off-again relationship with the oxen sealed the party’s fate. Our victory the year before was starting to look like a fluke.

(I died once again of a rattlesnake bite. You think I would’ve learned by now!)

The next week, we ventured out on the Oregon Trail for a fifth try. But the road was kind — despite several broken arms — and our lone survivor made it to the Promised Land! Success!

(The extreme cold got me again this time. Some Oregon Trail travelers just can’t be taught, I suppose.)

As you can see, getting all the way to Oregon is no small feat. Across 11 attempts and 68 travelers, only two true successful trips were made, and only 3 travelers saw Oregon’s Willamette Valley.

(And I died numerous times, but somehow, never of the dreaded dysentery.)

And yet, it was an absolute blast every time. The cruel turns of fate we met with laughter, not frustration, and the teamwork developed along the way was a genuine delight.

The Oregon Trail Card Game might not be everyone’s cup of tea, but I will always think of the game fondly.

Have you ever attempted the Oregon Trail in card game form, fellow players? Let us know in the comment section below! We’d love to hear from you.