UTRUNNING DEATH — When StefaN and Elena escape from Markos’ (guest star Raffi Barsoumian) control, only to find themselves stranded in a remote location, Stefan gets philosophical with Elena about her relationship with Damon. After their attempt to protect the dopplegangers goes badly, Liv (guest star Penelope Mitchell) and Luke (guest star Chris Brochu) come up with a dangerous new strategy. Damon recruits Matt and Jeremy to help him set a trap for Markos, who turns out to have a devastating surprise of his own. Bonnie finally admits to Caroline that she’s been keeping the truth about the Other Side from everyone. Finally, while Bonnie searches desperately for a way to stop Markos, Caroline is witness to an unthinkable act of violence by one of the Travelers. Michael Allowitz directed the episode written by Rebecca Sonnenshine (#521).
— OFFICIAL SYNOPSIS FOR THE VAMPIRE DIARIES: PROMISED LAND (EP521)
FLASHBACKS TO THE 1960s — Stefan tries to distract Elena from obsessing about the state of her relationship with Damon , while Bonnie does her best to be realistic about how the changes happening on the Other Side will affect her existence as the Anchor. Damon demands the Traveler knife, forcing Jeremy and Matt to admit it has gone missing. Through flashbacks to election night, 1960, Enzo (guest star Michael Malarkey) reveals to Elena, Stefan and Bonnie that he has learned what happened to his long-lost love, Maggie (guest star Heather Hemmens), and then, with the unwilling help of Liv (guest star Penelope Mitchell) and Luke (guest star Chris Brochu), things take an ugly turn. Trying to calm Enzo down, Damon intervenes, but his words cause Enzo to make a desperate and dangerous decision that leads to a violent confrontation with Stefan. Finally, Markos (guest star Raffi Barsoumian) enlists Sloan’s (guest star Caitlin McHugh) help in a ritual designed to break an ancient curse against the Travelers. Tyler is forced to play a dangerous part in the ritual, while witnessing the incredible power the Travelers now possess.
— OFFICIAL SYNOPSIS FOR THE VAMPIRE DIARIES: MAN ON FIRE (EP519)
PAUL WESLEY MAKES HIS DIRECTORIAL DEBUT — Both Stefan and Elena are suddenly having unsettling dreams of an alternate version of the life they might have had together. Bonnie has a disturbing encounter with Grams (guest star Jasmine Guy), who warns her about frightening changes on the Other Side. Enzo (guest star Michael Malarkey) gives Damon unwanted relationship advice, then admits he is searching for a woman he loved decades before while he was held captive by the Augustines. Liv (guest star Penelope Mitchell) enlists Matt, Jeremy and Tyler to help track the Travelers and keep them from taking control of Mystic Falls. Bonnie is hurt and angry when she learns that Jeremy is working with Liv behind her back. Luke (guest star Chris Brochu) shows up at the Salvatore house and explains what he knows about Markos (guest star Raffi Barsoumian) and the Travelers to Damon, Elena and Enzo. Matt has a terrifying encounter with inhabitants of the Other Side. Finally, when Damon finds Markos, he is both relieved and disturbed by what Markos has to tell him.
— OFFICIAL SYNOPSIS FOR THE VAMPIRE DIARIES: RESIDENT EVIL (EP518)