Some obvious examples
- the holodeck gets a fatal software error and people are stuck in a classic novel
- a shuttle breaks down and crashes into a habitable planet
- the federation loses a space battle, but thankfully there's some space jungle (nebula, asteroid field, etc) to hide out in, thankfully within sub light distances
I always find that very odd across the series. Don't get me wrong, I'm sure there are history dorks in the future, but it always seems like a missed opportunity to explore the what the dorks of the 23rd century may be in to. It seems like a big worldbuilding and character building creative opportunity. I'm sure there is more "current" stuff in their world people may be into.
Wolf 359 was an inside job