Surprise Halloween Episode Now Streaming
HBO Max delivered an unexpected treat for horror fans on Saturday, releasing a surprise 30-minute episode of “It: Welcome to Derry” at midnight to coincide with Halloween. Titled “A Story of Derry,” the special takes place hundreds of years before the events of the main series, following three youngsters who venture into the Western Wood and encounter a terrifying ancient spirit.
The episode, announced only through HBO and HBO Max social channels, explores the origins of the Shokopiwath tribe referenced in Episode 4 of the first season. According to the opening title card, the story is “the part we left out” of the gentler tales passed down to children. The special reveals the identity of the Indigenous warrior who created the dagger that can harm It, played by Zahn McClarnon, and includes references to Maturin, the cosmic turtle entity from Stephen King’s wider mythology. Directed by Tazbah Chavez and written by Cherie DiMaline and Jasmyne Flournoy, the episode stars Kimberly Guerrero, Kiawentiio, Morningstar Angeline, Isabel Deroy-Olson, Michael Podemski-Bedard, Thosh Collins, and McClarnon.
The surprise release comes weeks after HBO officially renewed the series for a second season in August 2026, and follows a first season that ranked among the top four series premieres globally in HBO Max’s history.
Season 2 Heads to 1935 with New Writing Talent
While the Halloween special streams now, attention is already shifting to Season 2, which will jump back to 1935—27 years before the first season—to depict the bloody massacre of the Bradley Gang, a group of bank robbers who stop in Derry for ammunition and encounter unimaginable horror. Showrunner Brad Caleb Kane, who previously co-ran the series with Jason Fuchs, will serve as sole showrunner for the new installment.
In an interview with Radio Times to promote his new series “Crystal Lake,” Kane confirmed that writing for Season 2 is underway and revealed that Ethan King, grandson of Stephen King, has joined the writing staff. “He’s brilliant and really smart. He’s a chip off the old block,” Kane said. “You can see why the Kings are how they are. It’s definitely passed down genetically through generations.”
The hiring is notable because Ethan King has no prior writing credits or published works, making “It: Welcome to Derry” Season 2 his first professional showcase. He joins a family literary legacy that includes his father Joe Hill (“Horns,” “NOS4A2,” “Locke & Key”) and uncle Owen King (“Sleeping Beauties”).
Production on Season 2 is slated to begin in summer 2027, with no release date announced. Kane has described the new season as “a Warner Bros. gangster picture through the lens of Pennywise and Stephen King.”
Why the Time Jump Matters
The expansion into different decades is central to the show’s design. Kane explained that the first season was anchored in the paranoias of 1962 America—the civil rights movement, the Cold War, and mistrust of neighbors—which It could weaponize. Season 2 will apply the same approach to 1935, a period of Depression-era anxiety and gangster mythology.
“We have to tell the story in that context,” Kane said, noting that Pennywise feeds on the fears of each era. The 1935 setting also aligns with the interstitials from King’s original novel, which trace the creature’s history in 27-year cycles.
What the Halloween Special Changes
The surprise episode adds a new layer to the established mythology by dramatizing the origin of the dagger that can wound It and by explicitly connecting the series to the broader King cosmology through Maturin. For viewers who followed the first season’s exploration of Derry’s indigenous history, the special provides answers that the main episodes only hinted at.
It also demonstrates HBO Max’s willingness to experiment with release strategies, dropping a self-contained story with little advance warning—a move that generated immediate social media buzz on Halloween. The special is now streaming, and with Season 2 writing underway and production set for 2027, the franchise appears positioned for a long stay in Derry.
For fans of King’s work, the addition of Ethan King to the writers’ room signals a deliberate effort to keep the adaptation within the family—and to deepen the lore that has made “It: Welcome to Derry” one of the streamer’s most-watched premieres.
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