Oregon Trail Jokes - 17 Hilarious Oregon Trail Jokes

Did you hear about the guy on the Oregon Trail who was shot for insulting the leader of his wagon train?

He died from dissin’ Terry.

My dog would have been great to bring in the Oregon Trail.

Her tail is a wagon.

I was playing an updated version of Oregon Trail voiced by Terry Crews.

I made the comment that he wasn’t a good voice actor, and the game abruptly ended. Apparently, I died of dissin’ Terry.

This joke may contain profanity. 🤔

You meet a man on the Oregon Trail. He tells you his name is Terry. “Terry?!” you say laughing, “Terry’s a girls name!” Without any hesitation, Terry pulls out a gun and shoots you dead.

You have died of dissin’ Terry :(

I played Oregon trail and made fun of a guy named Terry. He stabbed me...

I died of Dissin'-Terry

You’re traveling along the Oregon trail and you meet a man named Terry.

One of your party members says, “I thought Terry was a woman’s name.”

That party member immediately dies.

What did they die from?

Dysentery

How come the Ghostbusters never made it very far in Oregon Trail?

They refused to cross streams.

Adam and Terry woke up on the Oregon Trail with supplies for a month.

On the last week of the month, Adam fell ill. Terry on the other hand, was fine.

On the last day, Adam started to uncontrollably pester Terry because he thought Terry had poisoned him.

Terry was patient at first, but soon his patience wore thin. It didnt help that they had run out of...

A caravan of settlers were on the Oregon Trail

Their Indian guide repeatedly amazed them with his ability to find game and avoid hostile tribes. One day, he reigned in his horse and jumped down and put his head to the ground.
“Buffalo come,” was all he said.
“How can you know that?” Asked one of the amazed settlers.
He looked up and rep...

How much does a baker on the Oregon Trail pay for piercings?

A pie an ear.

Why wasn't drinking permitted on the Oregon trail?

It was important not to fall off the wagon.

Some guy on the Oregon Trail makes a joke at the expense of Terence, a known outlaw.

He died of dissin' Terry.

[NSFW] Oregon has legalized cocaine for a small amount.

They called it "The Oregon Trail".

What did settlers eat when they headed west?

Oregon Trail Mix.

I hope this joke doesn't die of dysentery.

When you're on the Oregon Trail don't make fun of Terrance, or he might kill you.

You don't want to die of dissin' Terry.

Did you know the original programmer of Oregon Trail was beaten to death by mentally ill Discworld fan?

He died of dissin' Terry.

The year is 1835...

The year is 1835, you’re traversing the Oregon Trail. You and your horse come upon a man, you introduce yourself, and he tells you his name is Terry. You laugh at him, and tell him Terry is a woman’s name. He shoots you point blank.

You’ve died of Dissin’ Terry

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