It Chapter 2 isn't actually a sequel to It Chapter 1, but a continuation of the same story--which means it does more than just pick up where Chapter 1 left off, it goes back and weaves all sorts of new information into the events we saw transpire back in 1989. While this is great--and an opportunity to check in with those lovable kids who starred in Chapter 1 all while keeping an eye on their adult selves--it also means that the timeline of events can get a little bit confusing with all the retroactive continuity being laid out.
It Chapter 2 Coverage
But never fear--we're here to help. By cross-referencing the details of the two movies--everything from the occasional month and year title card to the various outfits the characters wear--we've put together a complete timeline of events between It Chapters 1 and 2 to spell out not only the journey the Losers took across all 27 years of their ordeal, but also the history of Pennywise in Derry according to this version of the story, in chronological order.
A "Few Million Years" Ago
Pennywise arrives on Earth from space, crash lands in the area that would become Derry, Maine, and forms a nest deep underground.
The "Mid 18th Century"
The Shokopiwah tribe become the first known people to actually encounter and try to fight Pennywise, using the Ritual of Chüd, which fails.
~1864
Derry was officially founded as a beaver trapping town, but quickly befell a number of tragedies resulting in the entire town disappearing with no sign of an attack. The only clue was a trail of bloody clothes leading to the "well house." This marks the first major Pennywise attack on record.
1908
An explosion at the IronWorks Factory kills over a hundred people. Pennywise was the cause, somehow.
1935
A gang shootout between the Citizens of Derry and the Bradley Gang racked up a massive body count. Pennywise at fault.
1962
The Black Spot nightclub was burned down by a racist cult. Pennywise to blame.
Late 1988
Pennywise surfaces as a clown to lure the children of Derry to their deaths, claiming Georgie Denbrough as a victim.
June/July 1989
At the end of the school year Bill Denbrough, Richie Tozier, Stan Uris, and Eddie Kapsbrak begin investigating the Barrens to help Bill find clues about what happened to Georgie.
The Losers Club adds Ben Hanscom and Beverly Marsh after they intervene during an attack on Ben by the Bowers gang. Each individual Loser (except Richie) begins experiencing Pennywise nightmares while they're alone. Later, Mike Hanlon joins after the Losers save him from Bowers with a "rock war" in The Barrens.
Chapter 2 flashback: At some point after the rock fight, Ben finds and refurbishes the underground bunker in the woods to be the Losers clubhouse.
The Losers begin concocting their plan to attack Pennywise where it lives. They make their first trip into Neibolt house on July 4th, where Eddie breaks his arm and is whisked away by his mother. Bill and Richie get into a fight, resulting in a major break up for the Losers.
Chapter 2 flashback: Immediately after the fight, Bill walks (or, bike rides) Bev back home to her apartment where her father sprays her with her mother's perfume.
Chapter 2 flashback: Richie spends time playing Street Fighter at the theater arcade, before getting chased out by Bowers and his gang. Richie runs to the park, where he's attacked by Pennywise as the Paul Bunyon statue. At some point, either before or after the Pennywise attack, Richie goes to the Kissing Bridge to carve he and Eddie's initials.
Chapter 2 flashback: Bill rides his bike to the sewer where Georgie was killed to yell at Pennywise for not taking him instead.
Stan has his Bar Mitzvah. Only Richie attends.
Chapter 2 flashback: A closer look at the Bar Mitzvah where Richie remembers Stan's speech about "always being a loser."
Chapter 2 flashback: Ben begins attending summer school for what may or may not be history or social studies. He hallucinates Pennywise as Bev and is chased into his locker
Chapter 2 flashback: Eddie retrieves medicine from the pharmacy before "LOSER" is written on his cast. He hallucinates his mother in the basement and is attacked by the leper again.
August/September 1989
Eddie is told his medicine is a bunch of placebos. "LOSER" is written on his cast, which he corrects into "LOVER."
Henry Bowers is prompted by Pennywise to kill his father
Beverly fights her father but is taken by Pennywise immediately after she knocks him unconscious.
The Losers reunite and return to Neibolt to save Beverly. They take the fight to the sewers and defeat Pennywise.
Chapter 2 flashback: Pennywise's defeat washes a bunch of corpses and a very much alive Henry Bowers out of the sewers. Bowers returns home to find the police have discovered his father's corpse. He's arrested on the spot.
The Losers return to the Barrens after addressing some of their wounds and make their blood oath to return to Derry if Pennywise isn't gone in early September.
Bev explains that she will be immediately moving to Portland to live with her aunt.
2008
Bill Denbrough marries Audra Phillips.
Summer 2016
Pennywise reemerges in Derry, prompting Mike to reach out to each of the Losers to fulfill their promise
Stan receives Mike's phone call and decides to kill himself. Before he does, however, he writes a letter to each Loser explaining himself.
Henry Bowers escapes from the asylum with Pennywise's help.
Mike sends the Losers to uncover the respective "tokens." Bev returns to her apartment and is attacked by Pennywise as Mrs. Kersh. Richie returns to the movie theater arcade, and then to the park where he's attacked by Pennywise.
Richie returns to the inn, determined to leave before Ben talks him down.
Bill finds his bike Silver in an antique shop. He returns to his old house and has his new Pennywise encounter at the drain where Georgie was killed.
Eddie returns to the pharmacy to pick up a new inhaler, where he encounters his leper in the basement once more. When he returns to the inn to clean himself off, he's attacked by Henry Bowers, who stabs him in the face.
Richie, in the middle of sneaking out of town, returns to the synagogue where he remembers Stan's bar mitzvah.
Mike is attacked by Bowers in the library. Richie, after convincing himself to stay, saves Mike and kills Bowers.
The Losers (minus Stan, RIP) return to Neibolt House to face down Pennywise once and for all.
Eddie dies (double RIP) during the fight, but the Losers are ultimately victorious.
Ben and Bev begin a relationship, move onto a boat, and get a dog. Bill returns home to write a new book. Richie returns to the Kissing Bridge to re-carve he and Eddie's initials.
Each Loser gets a letter from Stan, explaining why he killed himself.
