My father actually took us kids on the Oregon Trail for vacation. ( Drove it east to west back roads and all.) Stopped at all the historical markers. Saw wagon ruts that were preserved baked in the mud.
Oh we also vacationed following Lewis & Clarke (except for the canoeing part -- we followed the course by road) , the Mormons, and the Sante Fe Trail. Basically, if there was a trail west we followed it on vacation.
I didn't realize how lucky I was as a kid.
Got to get my dad this shirt for Father's Day !