As Caroline and Elena prepare to host "Friendsgiving" at the dorm, they receive some hopeful news from Alaric and Stefan. Plus, flashbacks to Kai's (CHRIS WOOD) murderous past.
When the past comes back to haunt her, Elena is forced to face her problems head on. After a night out at the annual Whitmore Medical Center Fundraiser, Jo (recurring guest star Jodi Lyn O'Keefe) opens up to Alaric about her own tragic past. Meanwhile, Stefan, Matt and Enzo resort to extreme measures when Tripp (recurring guest star Colin Ferguson) withholds information about his vampire-killing operation, and when Sheriff Forbes (recurring guest star Marguerite MacIntyre) gets caught in the middle of a dangerous plan, Caroline is in a race against the clock. Elsewhere, Tyler and Liv (recurring guest star Penelope Mitchell) grow closer, and Damon stumbles upon a startling clue that renews his hope.
When Alaric realizes that Jo (recurring guest star Jodi Lyn O'Keefe) can't be compelled, he asks Elena to do some digging into her background. After learning that Enzo has been captured by Tripp (recurring guest star Colin Ferguson), Caroline teams up with Matt and Stefan to rescue him before Tripp learns their true identities. Armed with some new information about her past, Sarah (recurring guest star Gabrielle Walsh) breaks into Tripp's office and is surprised when she finds Matt there, doing some investigating of his own. Meanwhile, Elena is forced to deal with the consequences of her actions, and Jeremy hits rock bottom, lashing out in a destructive way. Lastly, Damon is determined to take matters into his own hands when he receives some upsetting news.
With Homecoming around the corner, Elena invites Liam (recurring guest star Marco James) to attend a party at the corn maze with her. Instead of attending the Homecoming festivities, Caroline is preoccupied after Stefan shows up unexpectedly and needs her help cleaning up a mess created by Enzo. Heeding Elena's advice to be more social, Alaric reluctantly attends the party, but a devastating accident quickly leaves him and Jo (recurring guest star Jodi Lyn O-Keefe) rushing to save lives. Elsewhere, Tyler finds himself in a dangerous position when his werewolf curse is put to the test, and an emotionally embattled Stefan comes clean to Caroline about his intent to move on from Mystic Falls. Lastly, Damon and Bonnie make an important discovery that affects their quest to get back home.
When Damon and Bonnie realize that uncovering a time in Damon's past may provide clues to finding their way home, Damon is forced to relive one of the worst days of his life. After an awkward run-in with Jo (recurring guest star Jodi Lyn) at the hospital, Alaric steps in to help Jeremy get his life together and cope with the loss of Bonnie. Elsewhere, Stefan attempts to show Elena what it's like to start over and create a new identity, while an unsuspecting Matt finds himself in a disturbing situation when Tripp (recurring guest star Colin Ferguson) lets him in on a dark secret. Lastly, Stefan, who is desperate to regain some normalcy in his life, is stunned when an unexpected visitor shows up.
In an attempt to bring some fun back into their lives, Elena persuades Caroline to meet her at the swimming hole where she plans to introduce her to Liam (recurring guest star Marco James – The Client List). Tyler, still working on controlling his anger issues, asks Liv (recurring guest star Penelope Mitchell – Hemlock Grove) for a favor and is surprised when she makes an unexpected confession. Stefan arrives back in Mystic Falls looking for Enzo and is caught off guard when he notices a strange change in Elena. Meanwhile, at the lake, Enzo's actions cause Matt to make a startling revelation, and Jeremy makes a discovery about the anti-magic spell that could potentially put Elena's life in danger. Elsewhere, Damon and Bonnie stumble upon clues that lead them to believe they're not alone.
Knowing she needs to come to terms with the loss of Damon, Elena turns to Alaric to help her move on with her life. Enzo convinces Caroline to join him as he tracks down a lead to get Damon and Bonnie back, but Caroline is shocked when they make an unexpected detour and uncover what Stefan has been up to. Meanwhile, Matt worries about Jeremy who is spending time with Sarah (recurring guest star Gabrielle Walsh – Paranormal Activity: The Marked Ones), a mysterious girl who has recently arrived in Mystic Falls. Elsewhere, Tripp (recurring guest star Colin Ferguson – Eureka), leader of the community protection program, makes an interesting confession to Matt about his connection to the town. Lastly, with the Other Side destroyed and gone for good, Damon and Bonnie reluctantly band together to uncover the mystery of where they are and how they are going to get back home.
In the season premiere, after spending four months coping with the loss of Damon in a potentially dangerous way, Elena returns to Whitmore College for her sophomore year.
Trailer to tease next season
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.
Bonnie has an unsettling encounter with Luke (CHRIS BROCHU), and learns more about his family history. The Travelers' leader, Markos (RAFFI BARSOUMIAN), arrives in Mystic Falls.
When Stefan tries to explain recent events to a very sick Elena, her first instinct is to call Damon. At the same time, Damon is trying to figure out how to make a disturbing confession to Elena. While going through Dr. Wes' files, Caroline discovers a frightening secret, and is surprised when Enzo (recurring guest star Michael Malarkey) appears, claiming to have the solution everyone is searching for. At Enzo's insistence, Caroline asks Stefan to meet her at a mysterious location where they are joined by a group of Travelers, including Sloan (recurring guest star Caitlin McHugh), who reveals new information on the importance of doppelgangers.
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