Pennywise just pulled off one more Halloween trick. HBO Max surprised fans Saturday by dropping an unannounced bonus episode of IT: Welcome to Derry, giving the Stephen King prequel series a new chapter nearly a year after Season 1 ended.
Titled “A Story of Derry,” the 30-minute special arrived at midnight on Halloween with virtually no advance promotion.
And rather than continuing directly from Season 1, the episode goes much further back.
Set hundreds of years before Pennywise, “A Story of Derry” follows three young people who venture into the Western Wood outside Derry and encounter a terrifying ancient spirit.
Tazbah Chavez directed the episode, and Cherie Dimaline and Jasmyne Flournoy wrote it. Its cast includes Kiawentiio, Brandon Oakes, Isabel Deroy-Olson, Michael Podemski-Bedard, Morningstar Angeline, Jennifer Podemski, Brenda Odjick, Kimberly Guerrero and Zahn McClarnon.
The surprise installment expands the mythology surrounding the evil haunting Derry rather than simply serving as an extra Season 1 episode.
It also arrives as HBO prepares to take the series even further backward in time.
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Welcome to Derry was renewed for Season 2 in August, with the next chapter moving from Season 1’s 1962 setting to 1935 during the Great Depression. The story will center on the Bradley Gang massacre, one of the catastrophic events described in the interludes of Stephen King’s novel.
Co-creator Andy Muschietti has previously said the larger plan was conceived as three seasons built around Derry’s recurring cycles of violence: the Black Spot fire in 1962, the Bradley Gang massacre in 1935 and the Easter egg hunt explosion of 1908.
That makes “A Story of Derry” something more interesting than a Halloween stocking stuffer.
It pushes the mythology back centuries beyond even those planned seasons and suggests HBO and the creative team are willing to explore Derry’s history outside the show’s main chronological structure.
The first season of IT: Welcome to Derry premiered in October 2025 and became one of HBO Max’s biggest series launches, helping secure the second-season renewal.
HBO has not announced a premiere date for Season 2. Until then, HBO just gave fans an extra half-hour of Derry to worry about.
“A Story of Derry” is streaming now on HBO Max.
