In the season finale, Damon's plan causes a huge explosion in Mystic Falls, and everyone is caught up in the confusion, leaving a trail of heroism, sacrifice, relief and despair.
When Stefan and Elena escape from Markos' (recurring 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 doppelgangers goes badly, Liv (recurring guest star PENELOPE MITCHELL) and Luke (recurring 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.
When Tyler turns up at the Salvatore house with the news that Markos' (recurring guest star RAFFI BARSOUMIAN) plan to break the witches' curse puts Stefan and Elena in imminent danger, Damon suggests they hide out in the remote cabin once owned by Caroline's father. Once there, it becomes obvious to Caroline that Stefan and Elena are keeping a secret, so Damon comes up with a parlor game designed to expose the truth. A ghostly presence at the cabin uses violence and fire to make itself known. Meanwhile, Matt takes charge of Tyler's plan to get information from one of the Travelers, and Bonnie continues to keep the truth about the Other Side from Jeremy, despite warnings from Grams (recurring guest star JASMINE GUY).
Through flashbacks to election night 1960, Enzo (MICHAEL MALARKEY) reveals to Elena, Stefan and Bonnie what happened to his long-lost love, Maggie (HEATHER HEMMENS – Hellcats).
Bonnie has a disturbing encounter with Grams (JASMINE GUY). When Damon finds Markos (RAFFI BARSOUMIAN), he is both relieved and troubled by what Markos has to tell him.
In order to keep Stefan from being harmed by Sloan and the Travelers, Caroline and Enzo agree to make a trip to Atlanta to find a newly discovered doppleganger.
When Stefan tries to explain recent events to a very sick Elena, her first instinct is to call Damon. While going through Dr. Wes' files, Caroline discovers a frightening secret.
While Nadia remembers her centuries-long search for her mother, Stefan, Caroline and Matt come up with a desperate new plan to save Elena’s life.
As Damon’s behavior escalates from destructive to deadly, Stefan begins to regret their last conversation and decides to track Damon down and intervene.
Hoping to help everyone move past recent traumatic events, Caroline convinces Elena and Bonnie to attend Whitmore College’s “Bitter Ball” for broken-hearted students.
When Enzo brings Damon a gruesome present and insists that they bond by committing an act of revenge, Damon makes an effort to do the honorable thing.
As she faces a new crisis, Katherine remembers the traumatic night in 1490 when she gave birth to the daughter who was immediately taken from her. Stefan lets Elena, Caroline and Bonnie know that Katherine's health has taken a turn for the worse, while Damon, Matt and Jeremy discuss some of Katherine's most notorious moments. Nadia (recurring guest star OLGA FONDA) comes up with a frightening plan to protect her mother, and Stefan and Elena are forced to help her. Meanwhile, Caroline is mortified when she realizes she forgot to fill Elena in on the latest shocking gossip, then indulges in a little scandalous behavior of her own. Finally, Elena and Katherine share an unexpected moment of connection.
Damon realizes Elena is in danger and enlists Stefan's help to find her. The brothers pay a visit to Aaron (recurring guest star SHAUN SIPOS), and Damon shocks Stefan by revealing his first-hand knowledge of Aaron's family. In an attempt to stop Damon, Dr. Wes (recurring guest star RICK COSNETT) unleashes his secret weapon, forcing Damon to deal with a part of his past he thought was gone forever, as well as the consequences of his decades-long plan for revenge. Meanwhile, Elena is horrified by Dr. Wes' confessions about the dark history of Whitmore College and his own ultimate goal. Finally, a frantic Katherine turns to Matt for help, until she realizes that Nadia (recurring guest star OLGA FONDA) may be the one who can solve her problem.
Elena turns to Aaron (Shaun Sipos) for help. Damon tells Elena about a terrible ordeal in his past that he has kept secret for decades. Stefan continues to offer Katherine support.
At Whitmore College, Elena and Caroline decide it's time to throw a big party, but their plans are interrupted when Jesse (recurring guest star KENDRICK SAMPSON) suddenly needs Caroline's help. At Elena's request, Damon comes up with an effective method to get Wes (recurring guest star RICK COSNETT) to answer his questions. At the party, Elena finds that she and Aaron (recurring guest star SHAUN SIPOS) have a lot in common, and Caroline grows more concerned about Jesse. Meanwhile, Katherine does a favor for Matt and manages to get through to Stefan, who is still struggling to overcome the events of the summer. Finally, Bonnie does her best to cope with her new reality, and Damon makes a terrifying discovery about a secret society.
The power of doppelgangers . . . While Elena and Damon try to explain Amara's (played by series star NINA DOBREV) situation to Stefan, Dr. Wes Maxfield (recurring guest star RICK COSNETT) gives Katherine some deeply disturbing news. Nadia (recurring guest star OLGA FONDA) shows up at Caroline's dorm room searching for Katherine. After a surprising conversation with Amara, Jeremy and Bonnie share a glimmer of hope. Silas fails to keep a promise, causing Damon to turn to Tessa (recurring guest star JANINA GAVANKAR) for help with his new plan, and Stefan makes a heartbreaking confession to Damon and Elena.
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