On September 29, The Vampire Diaries takes another trip back in time to flash back to Stefan’s past in the Chicago of the Roaring Twenties when Stefan and Klaus take their werewolf hunt to the Windy City. Stefan runs into a vampire, played by Claire Holt of “Pretty Little Liars,” who is nursing lingering feelings for him. The skinny from The CW is that this sequence will show us more shocking facts about Stefan’s Ripper days. While Stefan takes a trip down memory lane, Damon and Elena get a hot tip about his whereabouts and hit the road to find him. Tyler, meanwhile, takes his concerns about Caroline to Sheriff Forbes. He should just ask his mom.
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