HBO Max surprised horror fans on Halloween with a 30-minute special episode of “It: Welcome to Derry,” and the “Welcome to Derry” Halloween special ending ties directly into the franchise’s deeper mythology around Pennywise. The episode, titled “A Story of Derry,” jumps hundreds of years into the past, long before Pennywise terrorized the town in Season 1, according to IGN.
The surprise drop on Oct. 31 tells the full version of an origin story the main series only glimpsed, and it arrives while fans wait on the already renewed Season 2.
What happens in the Halloween special
“A Story of Derry” follows three young members of the Shokopiwah tribe who wander into the forbidden Western Woods and come face to face with an ancient spirit, according to Polygon. HBO’s official logline sums up the premise: “Hundreds of years before Pennywise, three youngsters venture into the Western Wood … where they encounter a terrifying ancient spirit.”
The episode opens with on-screen text framing the story as a buried piece of local history. As IGN reported, the text reads: “Generations ago, when the Kollu first preyed on our people, we left warnings for those who would come after. But we hid the truth inside a gentler tale, one our children could carry. This is the story we do not teach. This is the part we left out.”
That framing device positions the special as a hidden chapter of Derry folklore, a warning dressed up as a children’s story so the real horror could be passed down without alarming future generations.
The special builds out the vision Dick Hallorann (Chris Chalk) saw in Season 1, Episode 4, when he used his psychic abilities to look into a Shokopiwah man’s memories, according to TVLine. Necani (Kiawentiio) wants to hunt in the Western Woods to ease a meat shortage. When the elders, including her mother, Sesqui, refuse, she goes anyway with her friends Kino (Isabel Deroy-Olson) and Maneese (Michael Podemski).
In the woods, they meet Mitig (Zahn McClarnon), a stranger whose dagger drives the creature away. He tells them about Maturin, a great turtle that fought a cosmic war with the creature and banished it to Earth inside a falling star. Mitig isn’t the protector he seems, though. He has been sacrificing tribe members to the creature and plans to sacrifice the children too. They overpower him and take the dagger, and the creature kills him while they watch.
Who made the special
Tazbah Chavez (“Reservation Dogs”) directed the episode, which was written by Cherie Dimaline and Jasmyne Flournoy, according to SlashFilm. The creative team used the short runtime to expand the town’s history well outside the 1962 timeline that defined Season 1.
How the ending connects to Pennywise
The entity the children encounter is the Kollu, the Shokopiwah name for the being that would later take the form of Pennywise. Season 1 referred to it as the Galloo.
The ending shows how the Shokopiwah first trapped it. Kino uses a root she took from Mitig to meet Maturin, who reveals the cave where the Kollu was once imprisoned. Necani arrives with the dagger just in time to save Sesqui from the Kollu, but she’s too late to stop her mother from dying of a stab wound. The tribe then pulls 13 stones from the cave and forges a new cage, making the children of Maturin responsible for keeping the Kollu contained for generations, according to TVLine.
Those 13 stones are the pillars from Season 1 that keep Pennywise trapped in Derry. In 1962, Gen. Shaw (James Remar) removes and burns one of them, which reawakens It. Maturin’s appearance also ties the series to Stephen King’s “Dark Tower” universe, as Bloody Disgusting noted.
The special doesn’t suggest Derry’s evil predates the clown. It shows the same evil centuries before it put on the clown face, and it explains why the entity has never been able to leave.
Why this expands the Derry timeline
Season 1 of “It: Welcome to Derry” premiered on HBO on Oct. 26, 2025, and was set in 1962, focusing on residents’ encounters with Pennywise. The show functions as a prequel to Andy Muschietti’s “It” film duology from 2017 and 2019, according to Deadline.
HBO renewed the series in August 2026. Season 2 will jump back 27 years to 1935, during the Great Depression, and center on the massacre of the Bradley Gang. Muschietti has described the gang as bank robbers who stopped in Derry to buy ammunition, according to Gizmodo, before running into horror they could not have imagined.
The Halloween special’s jump even further back in time underscores how the franchise keeps working backward through Derry’s history. Muschietti has outlined a three-season plan built around the town’s biggest tragedies: the Black Spot fire in Season 1, the Bradley Gang massacre in Season 2 and the Kitchener Ironworks explosion in Season 3, according to GamesRadar+.
What’s next for the series
With Season 2 confirmed for a 1935 setting and the Halloween special pushing the mythology back centuries, the franchise now spans multiple distinct eras of Derry’s history. HBO hasn’t announced a Season 2 premiere date. Showrunner Brad Caleb Kane said filming begins in summer 2027, according to SlashFilm, and outlets estimate a debut in late 2027 or 2028. No further details on how the Kollu ties into future installments have been released.
Don't stop here
Every Score. Every Story. One Home.
Breaking sports, entertainment and news from across the Total Apex network, updated all day.
Get the Full Story →
