- Lexi visits Stefan in Mystic Falls to celebrate his 162nd birthday.
- Sheriff Forbes interviews Matt, Stefan, Jeremy and Elena regarding the disappearance of Vicki. She suspects there is a day walking vampire in town.
- Grams explains to Bonnie that the amber necklace is a talisman that belonged to her ancestor Emily Bennett and assures her it will protect her. Bonnie starts to experiment with magic and begins to learn how control it.
- Damon throws a party at the Grill. He feeds on and kills a male student, and compels his girlfriend to accuse Lexi of doing it. When the Sheriff and her deputies vervain her and take her outside, she overpowers them and tries to attack them. Damon rushes in and stakes Lexi in front of the Sheriff to win her trust. It is revealed that Damon killed Lexi to make the Council believe that they caught the vampire in town and keep them off their trail.
- Caroline's and Matt's relationship begins in this episode.
- Stefan stakes Damon, but says he will not kill him now because Damon saved his life.
(a couple of days could have passed, but not more than 2 or 3)
- Damon apologies to Stefan for killing Lexi.
- Emily haunts Bonnie's dreams, using the crystal talisman.
- Damon increases the pressure on Caroline to retrieve the crystal talisman from Bonnie.
- Alaric Saltzman arrives to Mystic Falls and replaces the deceased William Tanner as the new history teacher. He befriends Jeremy and Jenna.
- Stefan befriends Damon to find out what is his "diabolical master plan". It is to free Katherine from the tomb under Fell's Church. 26 other vampires are also entombed there.
- Bonnie, Elena and Caroline have a seance to speak to Emily, who possesses Bonnie and destroys the crystal talisman.
- In a fit of rage, Damon bites Bonnie and almost kills her. Stefan gives her his blood to heal her.
- Elena takes Bonnie back to her house and confesses to Bonnie about Stefan and Damon being vampires.
- Jeremy starts researching into the Gilbert journals and begins sketching again.
- Logan visits Jenna, and it is revealed that he is now a vampire.
(Matt had only "hung out" with Caroline twice. It's a full moon)
- Logan's victim is found. The Sheriff asks Damon to help with investigation.
- Damon compels Caroline to use the Gilbert Compass to locate Logan. He has been living in the Ramada, killing the staff and hiding the bodies.
- Logan won't tell him who gave him blood to turn into a vampire, but reveals that there are other vampires in town who also want to open the tomb, and claims they know how to open it.
- Alaric stakes Logan before Logan can reveal to Damon who these vampires are.
- It seems that the full moon influences Tyler and his father, Mayor Lockwood, and make them more angry and violent. Tyler gets in a fight with Jeremy at Career Night at school. Mayor Lockwood, angry at his son embarrassing him, takes Tyler and Jeremy outside and makes them fight each other "like real men". Alaric intervenes, and Tyler and the Mayor leave abruptly.
- Stefan and Elena make up and sleep together for the first time.
- Elena sees the picture of Katherine. She leaves the vervain necklace he gave her behind and drives away from Stefan's house, crying. She hits a man who is standing in the middle of the road, and her car flips several times before landing upside down. The man gets up and starts to walk towards her, indicating he is a vampire, but runs away when Damon appears. He helps her get out of the car and assesses her for injuries before she faints.
- Elena wakes up in Damon's car, and they are on their way to Georgia to Atlanta, to meet a witch called Bree, who owns a bar. He wants Bree help to open to tomb and free Katherine without the crystal talisman.
- We learn that Alaric has been hunting vampires, but Logan is the first one he found.
- Bree warns Lexi's boyfriend, Lee , that Damon is at the bar. He shows up with a vengeance and tries to kill Damon. Elena manages to talk him out of it, and thus saves Damon's life.
- Jeremy meets Anna, a vampire from 1864, who poses as a home-schooled student at the library.
- Bonnie has trouble doing magic after being attacked by Damon several days prior. Her grandmother tells her she must face her fears, which leads her to the tomb under Fell's Church. She falls into an underground cave, which leads to the tomb, and has no cell service to call for help.
- Stefan makes an alliance with Sheila, and rescues Bonnie from the cave in front of the tomb.
- Stefan confesses Elena when she returns home that he was the person who saved her from the car crash and reveals that he learned that she was adopted when researching into her connection to Katherine. Elena confronts Jenna about it.
- The vampire Elena hit with her car poses as a pizza delivery boy and manages to get an invitation inside Elena's house from Jeremy.
(Alaric had given Jeremy 2 weeks to finish his essay. We see Alaric return the essay graded so it could be longer than that, but characters talk as if it has just been a couple of days.)
- Stefan gives Elena vervain to give to all of her friends and family members to protect them.
- Matt starts working at the Mystic Grill as a busboy.
- Damon sort of apologizes to Bonnie for almost killing her.
- Stefan gives Elena the Gilbert Compass, so she can protect herself when it becomes clear the vampire she hit is stalking her.
- Jenna tells Elena that she had researched into her biological parents and learned that Elena's mother was a single teenager named Isobel, who ran away several days after Elena's birth. Grayson Gilbert delivered the baby, and he and his wife Miranda Sommers-Gilbert decide to adopt Elena, forging the birth certificates and other documents in case the government tried to take her away.
- Noah, Elena's vampire stalker, enters Elena's house and tries to kill her. She is saved by Stefan and Damon, and they agree to use her as bait at the 50's Decade Dance to get to him and kill him, since he had been invited in, putting Jeremy and Jenna at risk as well.
- Stefan makes a deal with Damon that he will help him open the tomb and get Katherine out, as long as the other vampires remain sealed inside the tomb.
- Caroline and Matt kiss for the first time.
- It is revealed that Noah is working with Anna, and that he was also obsessed with Katherine. They are looking for Emily's grimoire to open the tomb and free Anna's mother Pearl, a former friend of Katherine. Damon and Stefan stake him after torturing him for information.
- It's the 50's Decade Dance at Mystic Falls High School.
Unpleasantville ends with Damon and Stefan taking Elena to her house, so one can assume she slept there. Children of the Damned opens with Elena sleeping at Stefan's, so its assumed that it's a different night. More time could have passed, but Damon would likely not want to wait more than a couple of days to put his next plan in motion.
- Elena looks for the Gilbert Journals. She discovers that Jeremy loaned it to Alaric, who claimed to want to read a first person account of the Civil War, but really wanted to learn more about vampires.
- Stefan goes to retrieve the journal from Alaric, who tries and fails to stake him. Stefan tells him he has no interest in hurting him, but needs information.
- Stefan learns that Johnathan Gilbert left Emily's grimoire with Stefan's father, Giuseppe Salvatore. He guesses that it was buried with his father. He and Elena dig up the grave to recover it.
- Damon recognizes Anna, and she tells him she also wants to open the tomb. Anna asks him if he wants to work together, and Damon states that he only works alone.
- Bonnie develops a crush on Ben McKittrick. He asks her on a date, where she kisses him and gets a vision that he is a vampire. She tries to leave quickly, but he catches her and captures her at Anna's instruction.
- Damon discovers that Stefan and Elena have double crossed him, and in a fit of rage, feeds Elena his blood and threatens to turn her, causing Stefan to give him the grimoire to save his girlfriend.
- Stefan takes Elena home; when he goes downstairs to get Elena some aspirin, Anna kidnaps Elena from her bedroom.
- Stefan spends the whole night searching for Elena, while Damon ignores his calls; still angry about their betrayal. Stefan goes to Sheila Bennett to help find Bonnie and Elena using a locator spell.
- Anna takes Elena to the hotel room she is staying in with Ben, who knocked out Bonnie and put her in the bathtub. Anna leaves to bargain with Damon, as they each have a piece of what they need to open the tomb (Anna has Bonnie, Damon has the grimoire.) Damon refuses, showing his anger that Anna put Elena in danger.
- Elena and Bonnie eventually escape after Anna leaves when Stefan arrives and pushes the door wide open to allow the sunlight to come in, which burns Ben and forces him to hide. Stefan tells him to get out of town, or he will kill him.
- Anna returns to find Elena and Bonnie gone, and Ben crouched behind the bed to avoid the sun. She is visibly angry, until she is able to concoct a new plan: wait for Damon to open the tomb, and then fight her way in, using Jeremy's blood to awaken her mother, as she has gone 145 years without blood.
- Elena and Damon reach an "understanding", and convinces him to trust her and Stefan again. She offers to help him open the tomb, as long as only Katherine is rescued. Damon is hesitant but agrees, demanding that he not break his trust again.
- Sheila agrees to open the tomb and rescue Katherine, as long as they burn all the other vampires inside, so that everything can be over and no one else gets hurt.
- Anna lures Jeremy to the woods, and he kisses her. Anna's vampire face emerges, and she turns away from him. Jeremy notices something weird is happening, but Ben knocks him out before he could ask more.
- Stefan burns Ben when Ben threatens to attack him, assuming that Stefan was weak because of his "vegetarian" diet.
- Damon takes Elena into the tomb with him, to ensure Sheila and Bonnie don't trap him in. Anna shows up and forces her way into the tomb as well. Bonnie scolds Sheila for allowing her to go in, and Sheila reveals that she didn't unseal the tomb, she only opened the door; Damon and Anna are trapped with the other vampires, but Elena as a human can still get out. Stefan returns and is angry when he learns that Damon is trapped.
- Damon and Elena look around the desiccated vampires to find Katherine. Anna enters and attacks Elena, biting her wrist and forcing it into her mother's mouth to feed her, saying that the Gilbert's are the reason she's in here, and that the Gilbert's blood is what will get her out. Stefan hears Elena's screams and runs in to find her.
- Bonnie, who doesn't want Stefan to be trapped, tells Sheila that she will try to open it herself if Sheila won't help her. Stefan walks Elena out, and then reveals that he can't leave. Elena is visibly upset that he is stuck. Bonnie finally convinces Sheila to unseal the tomb, and they begin to do the spell.
- Knowing that they won't be able to keep the tomb open for long, Elena and Stefan run in to tell Damon to hurry. Damon is visibly distraught, because Katherine is nowhere to be found. He throws the blood bag he brought to wake up Katherine against the wall and it splatters everywhere.They tell him that they have to go or they'll be stuck forever, and finally convince Damon to leave.
- Anna walks out with Pearl, and apologizes for her involvement, explaining that she only wanted to free her mother. Stefan, Elena and Damon make it out just before the seal is closed again. Bonnie and Sheila are noticeably worn out.
- Damon laments the fact that Katherine wasn't in the tomb, and thus out there somewhere, without him. Elena and Bonnie go to Sheila's house to rest. When Bonnie goes to check on her Sheila, she finds her dead in her bed.
- One of the tomb vampires (Harper), licks at the blood that splattered on him. He pulls himself up, pushes open the door and escapes into the night.
Harper asks the man what year it is, and he says it's 2010. I believe its a mistake, and that its still the end of 2009
- Harper feeds from a hiker and takes his clothes, leaving his cell phone, whose ringing startles him. He walks into the town square and is overwhelmed by the speeding cars, people walking in modern clothes, skateboarding and talking on cell phones. He catches the eye of a woman sitting at a bus stop, who looks at him and smiles, with a slight nod in acknowledgment.