HBO Max released a surprise 30-minute special titled A Story of Derry
on October 31, 2026. The unannounced Halloween episode explores the origins of IT hundreds of years before Pennywise terrorized the Maine town, arriving while showrunner Brad Caleb Kane and the writers’ room script the second season.
Surprise Halloween Special Reveals Early History of Derry
The unannounced 30-minute release rewinds the clock far beyond the timeline of the first season. Titled A Story of Derry
, the special debuted at midnight on Saturday, October 31, 2026, streaming directly on HBO Max. Directed by Tazbah Chavez, the narrative follows three young people venturing into the Western Wood, where they encounter a terrifying ancient spirit
alongside a cosmic counterweight to the entity that becomes Pennywise the Clown.
The special serves as a direct companion piece to the fourth episode of the main series. That earlier chapter featured a vision sequence experienced by Dick Halloran, which showed how the Indigenous residents of the region first fought against the entity. The Halloween release fills in the blanks left by that ancient clash, showcasing an early North American tribe struggling for food before stumbling upon the dark force lurking beneath the land.
Maturin the Turtle Appears in Stephen King Adaptation
The episode brings in Maturin the Turtle, a massive cosmic deity referenced throughout The Dark Tower
series as one of the Twelve Guardians of the Beams. In King’s mythology, Maturin represents creation, wisdom, and peace as the ultimate nemesis to Pennywise’s chaos and destruction. While the feature films only hinted at the character, the streaming special gives the benevolent deity a physical, cosmic appearance during a sequence in the woods.
IT's a surprise Halloween treat.Catch this never-before-seen special exploring the origins of IT in Derry. #AStoryOfDerry is streaming now on HBO Max. 🎈 pic.twitter.com/BpXHZHdlQU
The main teenage trio in the special is led by Kiawentiio, alongside Morningstar Angeline and Zahn McClarnon. Written by Cherie Dimaline and Jasmyne Flournoy, the compact episode utilizes a stark opening in an Indigenous language before shifting to English, drawing comparisons to survival dramas like Prey
.
Second Season of It: Welcome to Derry Prepares for Production
Showrunner Brad Caleb Kane told Deadline that the upcoming episodes will introduce a different kind of Pennywise, Pennywise the way you’ve never seen that character before.
We’re writing the scripts. We’re about halfway through the writing of the scripts. We have a production schedule, we’re greenlit for a Season 2, and Andy Muschietti’s out there casting.
Brad Caleb Kane, Showrunner
Set in 1935 during the Great Depression, Season 2 will jump back 27 years prior to the events of the first season. Executive producer Andy Muschietti explained that the new setting will carry a bleak aesthetic defined by economic hardship and desperation.
There’s gonna be a lot of that depression-era hustling in the air in our characters. Everybody’s trying to get by and survive the circumstances. They are gonna do crazy things.
Andy Muschietti, Executive Producer
The plot centers on the bloody massacre of the Bradley Gang, a crew of bank robbers who stop in Derry to purchase ammunition and end up facing supernatural horror. Production on the second season is scheduled to begin filming in 2027, with a prospective release window falling in late 2027 or early 2028 on HBO Max.
‘IT: WELCOME TO DERRY’ has released a new special episode as a Halloween surprise.Titled “A Story of Derry,” the episode takes place hundreds of years before Pennywise.Now streaming on HBO Max. pic.twitter.com/0gVYCbSn6T
More on HBO Max
IT's a surprise Halloween treat.Catch this never-before-seen special exploring the origins of IT in Derry. #AStoryOfDerry is streaming now on HBO Max. 🎈 pic.twitter.com/NH3NcMLt8n
🎃 ‘IT: WELCOME TO DERRY’ surprises fans with a special Halloween episode!Titled “A Story of Derry,” the episode takes place hundreds of years before Pennywise.Now streaming on HBO Max! 👻#ITWelcomeToDerry #Pennywise #ITChapter #HBO #HBOMax #StephenKing #WelcomeToDerry… pic.twitter.com/x7kW9ndjcO