Hitch up your wagon and hit up the general store for supplies because it's time to head out on The Oregon Trail. A collection of more than Robyn Itule: Jeremy did you play Oregon Trail when you were. So I think title- ing , its a bit more creative, I think it may be more And there's information about. to be the least productive year yet for Millennials! We can now play The Oregon Trail online totally free with no need to download anything. Play 'Oregon Trail,' more online - FOR FREE Just watch out for those bandits -- and try not to shoot all the buffalo, eh? A big ol' tip of the hat.