Why Did All Children of a Certain Age Play Oregon Trail?

It all started with a teletype mainframe in a janitor’s closet

I was out in San Francisco with friends, just a week after being in Oregon’s Willamette Valley — specifically, Portland. We chatted about HBO’s Westworld, which led to a discussion of topics including (but not limited to) robots, pioneers, reality, and the American West.

Naturally, our nostalgic, uninhibited conversation brought us to memories of grade school and the Oregon Trail video game. Every person in our group had vivid, formative memories of playing that game. Talk to any adult between 21 and 41 years old, and they’ll say the same. Why is that?

How did The Oregon Trail start?

The first incarnation of The Oregon Trail was a dice board game conceived by Don Rawitsch. The game was not unlike Dungeons & Dragons. It was designed to engage students in the history of Jefferson, Lewis & Clark, Western expansion, and the like. Rawitsch sketched the first version on a piece of butcher paper and traced a path from Independence, Missouri, to Willamette Valley, Oregon. Like many role-playing games, players collected money and goods that could be traded. A roll of the dice determined the player’s (mostly dire) fortunes, such as broken legs, wagon axles…