HBO Max waited until Halloween to spring a surprise on IT: Welcome to Derry fans. A brand-new bonus episode, “A Story of Derry,” appeared on October 31 with no advance announcement, and it takes the franchise further back in time than it has ever gone. Here’s what we know, how to find it, and what it could mean for season 2.
“A Story of Derry” is a roughly 30-minute special set hundreds of years before Pennywise. The official synopsis says three youngsters venture into the Western Wood and encounter a terrifying ancient spirit. It’s streaming now on HBO Max, and HBO released two teasers alongside it.
The Notes
- Release date: October 31, 2026, dropped on HBO Max as a Halloween surprise.
- Runtime: About 30 minutes.
- Setting: Hundreds of years before Pennywise, in the Western Wood, long before Derry was a town.
- Story: Three young people meet a terrifying ancient spirit in the woods.
- Pennywise: According to SlashFilm, he does not appear in this episode.
The story
A surprise drop. There was no trailer campaign or press push ahead of time. The episode simply showed up on HBO Max at the start of Halloween, which is why several outlets called it a surprise special. Bloody Disgusting noted that the rumors beforehand turned out to be true.
Where to watch. SlashFilm reports that some viewers had trouble finding it. If you don’t see it in the main episode list, check the “Related” tab on the Welcome to Derry page.
Who made it (reported). SlashFilm credits Tazbah Chavez (Reservation Dogs) as director and Cherie Dimaline and Jasmyne Flournoy as writers. I could only find those credits in that one report. Dread Central and iHorror didn’t name a director or writers, and no cast has been listed in anything I could read, so treat the credits as unconfirmed until HBO publishes them.
The Indigenous history. SlashFilm also says the episode centers on the Shokopiwah tribe, the fictional Indigenous people who lived on the land before it became Derry and who first appeared in season 1, episode 4. That would make it the show’s deepest dive yet into the history of the place where IT feeds. The series has pointed to that history since season 1, and this special reportedly goes much further back.
What it means for season 2
The special lands between seasons. Season 1 ended on December 14, 2025, and season 2 has been renewed but has no premiere date. Reporting says season 2 jumps to 1935 and the Great Depression, centering on the Bradley Gang massacre, one of the Derry interludes from Stephen King’s novel. Brad Caleb Kane is the sole showrunner, and Bill Skarsgård is reported to return as Pennywise. Bloody Disgusting also reported on October 16 that season 2 will feature a Pennywise “you’ve never seen before.” An August Syfy explainer estimated a premiere in late 2027 or early 2028, but that is an estimate, not an announcement.
Quick facts
| Detail | Info |
|---|---|
| Title | “A Story of Derry” |
| Series | IT: Welcome to Derry (HBO Max) |
| Release date | October 31, 2026 |
| Runtime | About 30 minutes |
| Setting | Hundreds of years before Pennywise; the Western Wood |
| Director (reported) | Tazbah Chavez |
| Writers (reported) | Cherie Dimaline and Jasmyne Flournoy |
| Where to watch | HBO Max, under the “Related” tab on the series page |
What we still don’t know
- Who stars in the special
- Whether the director and writer credits are confirmed by HBO
- Whether the special has any direct tie to the season 2 story
- When season 2 will premiere
Sources & further reading
- Bloody Disgusting: HBO Max releases a new Welcome to Derry bonus episode
- SlashFilm: Welcome to Derry prequel episode released for Halloween
- Dread Central: Surprise Halloween special
- iHorror: Halloween special drops without warning
- Variety: Surprise Halloween special
- TV Insider: Surprise special hits HBO Max
- Bloody Disgusting: Season 2 will feature a Pennywise you’ve never seen before
- Bloody Disgusting: Renewed for a 1935-set second season
- Syfy: Everything to know about season 2
Last updated November 1, 2026.