The question is pretty simple: From the ensemble of characters on the show which ones would you enjoy seeing in a historical setting? Like Applejack in Austin when Texas was a Republic in the 1830s or Twilight in Baghdad during the Abbasid Caliphate in the 800s. It dosen't matter what character it is or when and where in history they are sent to. What events would you enjoy the most in seeing them be witness are wrapped up in? What historical figures would you enjoy them meeting or interacting with? Just interested in people's thoughts.

Shining Armor and Cadence aboard RMS Titanic. Would probably be a better love story than what Cameron conjured up.

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Mane Six in prehistoric time accidentally teaching first humans about fire. And thus humanity was uplifted.
RAINBOW!
What? Was just a harmless lightning prank.

Maybe Twilight in the American Revolution and she would mess with history by bringing friendship between 13 colonies and the British crown and thus the rightful monarchy would remain.
Of course the monarchy is the true path to peace, princess Twilight says so

That's all silliness I thought of for now.

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Twilight meeting Erwin Rommel during the Africa campaign/ during the defence of the D-day invasion. Maybe Twilight can help Rommel plan out some tactics to be used on both fronts.

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The French would like to have a word with the Princess of Friendship...

Now THAT would be a time and place for Twilight to go.
(you can also throw in Rarity for the heck of it)

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A devoutly Catholic kingship on one side, a communist (and yes, the Jacobins - more precisely, the Montagnards - were communists, or at the very least "revolutionary socialists" - they just weren't Marxists, what with Marx not even being born yet and all) anti-monarchy revolution on the other...

Yeah, there's nowhere even remotely safe for Twilight there.

6221634
Any revolutionary movement would not be safe for her or for any character:
Russian Revolution
Cuban Revolution
Mexican Revolution
Even the a fore mentioned American Revolution wouldn't be safe.
Pretty much any time period and place where humans are killing each other over ideology basically.

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Starlight Glimmer in communist russia
LL

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Salve Equitium, why not have the six heroes travel to the 4th Century AD, when the Roman Empire was divided in two.