Damon and Alaric face an old enemy after they obtain a weapon that may be able to destroy Cade. Meanwhile, Stefan is held captive by a surprising acquaintance and is forced to confront a dark secret from his past; and Cade digs deep in Bonnie's mind.
Damon makes a deal with Cade to retrieve the Maxwell journal, in an effort to save Stefan's soul, but Alaric and Matt refuse to hand the journal over because it may contain the key to destroying Cade. Meanwhile, Caroline desperately tries to connect with Stefan before Cade goes through with his plan.
Cade returns to Mystic Falls and presents Damon and Stefan with additional assignments, each with unthinkable consequences. Meanwhile, Caroline and Matt do their best to protect the town's residents from Cade's appetite for their souls; and Bonnie and Enzo hit the road on a romantic trip, taking the bell with them in an effort to keep it safe.
Sybil enacts revenge on Damon by putting him in a catatonic state. Caroline and Bonnie enter Damon's mind and run into familiar faces from the past, only to discover Stefan is the key to Damon's fate. Meanwhile, Sybil and her sister, Seline, jockey for control of the bell.
Stefan and Damon return to Mystic Falls at Sybil's request as she still searches for the historical artifact; Bonnie returns from Paris wearing a vile of Enzo's blood, which makes Caroline wonder if Bonnie will become a vampire; Stefan, Damon, Caroline, Bonnie and Enzo attend the Miss Mystic Falls pageant; Sybil taunts Damon with memories of Elena.
Stefan and Damon attend an anger management support group looking for their next victim. Meanwhile, Sybil uses a group of high school students as leverage to get Caroline to locate a historical artifact that can be used against her; and Stefan and Damon continue their commitment to Cade and test the morals of a young doctor.
Stefan's Christmas Eve dinner with Caroline is crashed by Damon and Sybil, and things quickly take a dark and twisted turn. Meanwhile, in a series of flashbacks to Stefan's past, Cade's attempt to entice him with his mysterious agenda leaves Stefan faced with an unimaginable decision.
Caroline takes drastic measures to ensure her family's safety when her children become the focus of the Siren's latest plan, and Stefan pledges to do everything he can to save the twins. Meanwhile, Enzo is unable to fight off Sybil's latest move; and Stefan dives into his subconscious and sets off a chain of events that leaves him faced with a life-changing decision.
Damon spirals down a dangerous path of self-destruction, which forces Stefan to make a gut-wrenching decision that threatens to change their relationship forever. Meanwhile, Bonnie gets advice from Caroline on how to break through to Enzo; and Matt attempts to decipher a mysterious box of messages that he received. Finally, after tragedy strikes close to home, Stefan and the others are forced to remember what matters most to them.
Tasked with finding a mysterious artifact, Damon's latest mission takes him to Texas where a violent run-in with Peter Maxwell leads to a surprising revelation. Meanwhile, Stefan and Alaric uncover the origins of the mysterious force they're up against; and Matt returns to the fray after his past and present collide in an unexpected way.
Enzo continues to fight the control over him; Bonnie is forced to make a heart-wrenching decision involving two of the most important people in her life; Alaric researches a mysterious artifact that may help bring Damon and Enzo back; Damon's downward spiral leads him to Tyler Lockwood who tries to talk some sense into him before it's too late.
After learning that someone from Stefan's past may be Damon and Enzo's next target, Stefan, Bonnie and Caroline head to North Carolina. There, Bonnie takes drastic measures in an attempt to break Enzo free of whatever has a hold over him. Meanwhile, at the armory, Alaric and Georgie stumble upon a mysterious symbol that may be related to the supernatural force controlling Damon and Enzo.
Season 8 begins with Stefan searching for Damon and Enzo after they mysteriously vanished months ago from the Armory vault. Meanwhile, Caroline and Alaric fear that someone is targeting their family after they encounter an unexpected visitor.