It: Welcome to Derry has given fans an unexpected reason to return to its terrifying universe this Halloween. Just when audiences were looking ahead to the show’s second season, HBO Max surprised viewers with a completely new special that reaches far beyond the history explored in the first season. Its story takes place in an era when the town of Derry did not yet exist in its familiar form, raising fresh questions about the supernatural presence connected to the land.
Titled “A Story of Derry,” the approximately 30-minute special arrived on October 31, 2026. Rather than continuing the main storyline, the release takes viewers centuries into the past, exploring an encounter with an ancient supernatural spirit that predates the familiar Pennywise mythology.
‘A Story of Derry’ takes viewers hundreds of years before Pennywise
The biggest surprise about the Halloween special is its historical setting. While the first season of It: Welcome to Derry explored events in 1962, the new release travels hundreds of years further into the past.
According to its official description:
“Hundreds of years before Pennywise, three youngsters venture into the Western Wood … where they encounter a terrifying ancient spirit.”
The brief synopsis introduces three young characters whose journey into the Western Wood brings them face to face with something supernatural. It also establishes that the entity’s history extends much further back than the events audiences have seen in the television series and Andy Muschietti’s It films.
The setting is particularly interesting because the Western Wood is already connected to the show’s earlier exploration of Derry’s supernatural past. The special returns to that historical territory, giving the franchise an opportunity to explore an earlier chapter of its mythology.
Contemporary reporting has identified the fictional Shokopiwah, an Indigenous group established within the television series, as central to the special’s historical focus. However, HBO’s official synopsis does not provide a detailed explanation of the group’s involvement or reveal the complete story.
That distinction matters because some early discussions surrounding the surprise release included theories about what the episode might uncover. Those interpretations should not be confused with the official description of the special.
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How the Halloween special connects to ‘Welcome to Derry’ Season 1
Although “A Story of Derry” introduces a much earlier period, its mythology is not entirely disconnected from what viewers have already watched.
One important connection comes from Season 1, Episode 4, which featured a historical sequence involving Indigenous people who encountered and fought the entity long before the main events of the series.
That sequence established that the supernatural threat associated with Pennywise had existed in the region before the familiar town of Derry became the setting of the story.
The Halloween special revisits this earlier history and expands on elements introduced through that episode. It also provides additional space to explore the relationship between the ancient supernatural presence and the land that eventually becomes Derry.
The story therefore goes beyond simply showing another appearance of Pennywise. Instead, it explores an earlier chapter of the mythology surrounding IT, the supernatural entity at the centre of Stephen King’s It.
Some post-release coverage has also identified further connections to the mythology presented in the first season and King’s original novel. These are developments within the released special, rather than details HBO disclosed in its initial promotional description.
For viewers expecting a direct continuation of the Season 1 finale, the distinction is important: this is a historical story within the larger It universe, not a conventional continuation of the 1962 storyline.
Who directed ‘A Story of Derry’? Meet the cast and writers
The Halloween special brings together a creative team and cast connected to the Indigenous history explored within the series.
Tazbah Chavez directed “A Story of Derry,” with Cherie Dimaline and Jasmyne Flournoy credited as its writers.
The cast includes:
- Kiawentiio
- Brandon Oakes
- Isabel Deroy-Olson
- Michael Podemski-Bedard
- Morningstar Angeline
- Jennifer Podemski
- Brenda Odjick
- Jennifer Guerrero
- Zahn McClarnon
- Eric Trask
Several performers associated with the first season’s historical storyline return in different roles, while Zahn McClarnon joins the cast for the special.
The casting reflects the episode’s focus on an earlier period within the show’s fictional Indigenous history. Since the story takes place centuries before Pennywise, it moves away from the character-driven narrative audiences followed during the first season and concentrates on a much older chapter of the supernatural mythology.
Why ‘It: Welcome to Derry’ Season 1 matters to the new special
To understand the significance of the Halloween release, it helps to look at where the television series began.
The first season of It: Welcome to Derry was set primarily in 1962, placing its events 27 years before the story depicted in the 2017 It film.
Based on Stephen King’s 1986 novel It, the HBO series expands the historical material and mythology associated with the book while also building on the world established by Andy Muschietti’s film adaptations.
The first season followed Derry’s residents as the community confronted the return of the supernatural entity most famously known through its Pennywise the Dancing Clown appearance. Bill Skarsgård played Pennywise, continuing the character he portrayed in the two It films.
Developed for television by Andy Muschietti, Barbara Muschietti and Jason Fuchs, the series consisted of eight episodes. It premiered on HBO and HBO Max in October 2025.
HBO also revealed that the show ranked among the top four series premieres globally in HBO Max history, making it one of the platform’s strongest global series launches.
The Halloween special now adds another historical layer to the universe established by that first season.
‘Welcome to Derry’ Season 2 moves back to 1935 during the Great Depression
While “A Story of Derry” travels centuries into the past, the next full season will explore a different period in the town’s history.
HBO renewed It: Welcome to Derry for Season 2 on August 17, 2026. The upcoming season will move the timeline from 1962 to 1935, during the Great Depression, and focus on the Bradley Gang massacre.
The storyline draws from one of the historical interludes in Stephen King’s original It novel.
HBO’s official description explains the central event:
“the bloody massacre of the Bradley Gang, a group of bank robbers who stop in Derry to buy ammo and end up facing unimaginable horror.”
The story will follow the gang’s arrival in Derry and the horrifying events surrounding its stop in the town.
The second season will also have a different leadership structure behind the scenes. Brad Caleb Kane will serve as the sole showrunner, following his work as co-showrunner during Season 1 alongside Jason Fuchs.
Andy and Barbara Muschietti will remain executive producers, together with Kane, Roy Lee, Dan Lin, Jamie Travis and Dhana Gilbert.
The series continues to be produced by HBO and Warner Bros. Television.
Season 2 scripts are being written as development moves forward
The renewal announcement has been followed by further progress on the upcoming season.
By October 2026, Season 2 was already in active development. Brad Caleb Kane confirmed that scripts were being written and that production had been greenlit. Andy Muschietti was also involved in the casting process.
Kane described the upcoming season as a larger production and indicated that its 1935 setting would allow the creative team to explore a very different social and economic environment from the suburban world presented in Season 1.
Muschietti has also discussed the broader historical structure envisioned for the series, drawing on major events from the interludes in King’s novel.
The three historical events identified within that wider creative concept are:
| Historical period | Storyline | Status |
| 1962 | The Black Spot | Incorporated into Season 1 |
| 1935 | The Bradley Gang massacre | Announced as the focus of Season 2 |
| 1908 | The Easter egg hunt explosion | Discussed as part of the broader concept |
Although the creators have discussed the 1908 Easter egg hunt explosion as part of their wider plans, HBO has not officially announced a third season or confirmed that storyline as a future season.
As of October 31, 2026, there is also no confirmed premiere date for Season 2.
Bill Skarsgård is expected to return as Pennywise in Season 2
The historical setting of the second season does not mean that Pennywise will disappear from the story.
Bill Skarsgård is expected to return as Pennywise for Season 2, continuing his portrayal of the supernatural character from the first season and Muschietti’s two films.
Brad Caleb Kane has also discussed plans to introduce a different version of Pennywise within the 1935 storyline.
However, those comments should not be interpreted as confirmation of a completely separate identity or a replacement performer. They concern the way the character will be portrayed within the different historical setting.
This is another important distinction between Season 2 and “A Story of Derry.” The Halloween special focuses on an ancient chapter of the mythology, whereas the upcoming full season is expected to continue exploring Pennywise’s history through another significant period in Derry’s past.
‘A Story of Derry’ is not Season 2’s first episode
With the special arriving between seasons, viewers may wonder whether it forms part of the upcoming season’s episode count or replaces an instalment of the main series.
It does neither.
“A Story of Derry” is a standalone Halloween special released between Season 1 and Season 2. It is not the first episode of the upcoming season, and its release does not change the announced 1935 setting of the next full season.
Instead, it gives the franchise room to explore an era that predates both the 1962 events of Season 1 and the 1935 events planned for Season 2 by centuries.
The release also follows an earlier Halloween surprise involving the series. In 2025, the second episode of It: Welcome to Derry became available on Halloween, two days ahead of its originally scheduled release date.
This time, HBO Max went further by releasing an entirely new special rather than bringing forward an existing episode.
Where to watch ‘It: Welcome to Derry: A Story of Derry’
The approximately 30-minute special premiered on October 31, 2026, and is available to stream on HBO Max.
It can be watched separately from the eight-episode first season. Reporting on the release has also confirmed the availability of an ASL version.
For viewers who have already watched Season 1, the special offers another look at the historical mythology introduced through the Indigenous encounter in Episode 4. Those approaching the story separately can follow its central premise through the official description: three youngsters venture into the Western Wood hundreds of years before Pennywise and encounter an ancient spirit.
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If you want to watch a compelling crime drama with an atmospheric setting and an ongoing mystery, explore our Shetland Season 11 release date report for the latest details.
Conclusion
With “A Story of Derry,” It: Welcome to Derry has expanded its supernatural history beyond the familiar timelines of its television and film stories. The Halloween special explores an ancient encounter centuries before Pennywise, while the confirmed second season will return to 1935 to tell the story of the Bradley Gang massacre.
The two projects serve different purposes within the franchise, but both continue its exploration of Derry’s disturbing past. The special is already streaming on HBO Max, while Season 2 remains in development without an announced premiere date.
Source and research disclaimer: This article has been prepared through research of the sources provided below, including reporting from TV Insider, TVLine, TheWrap, Variety, SlashFilm, UPI and Dark Horizons, alongside the supplied HBO Max and Warner Bros. Television renewal information. Details reflect the information available in those sources as of October 31, 2026. Official descriptions, reported production updates and post-release coverage have been distinguished wherever applicable. Further details may emerge as HBO releases additional information about the special and the second season.
Sources
- HBO Max / Warner Bros. Television Season 2 renewal information
- TheWrap: ‘It: Welcome to Derry’ Season 2 renewal
- TV Insider: ‘A Story of Derry’ special details and cast
- TVLine: Halloween special and Season 2 timeline
- Variety: Season 2 setting, development and series background
- SlashFilm: ‘A Story of Derry’ and its historical setting
- UPI: HBO Max Halloween special release
- Dark Horizons: October 2026 Season 2 production update
Featured Image Credit: HBO Max / Warner Bros. Television
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