‘IT: Welcome to Derry’ Drops Surprise Halloween Special ‘A Story of Derry’ Set Hundreds of Years Before Pennywise

Few horror franchises know how to time a scare quite like the world of Stephen King’s ‘IT’. This Halloween, HBO surprised fans with an unannounced ‘IT: Welcome to Derry’ special that rewinds the clock far beyond anything the series has shown so far.

The release arrived at midnight on Saturday, October 31, and it is now streaming on HBO Max. HBO’s promotion described it as a never-before-seen special exploring the origins of IT in Derry.

Titled ‘A Story of Derry’, the 30-minute episode is set hundreds of years before Pennywise ever terrorized the town. It follows three young people who venture into the Western Wood and run into a terrifying ancient spirit.

The special opens with a title card that signals it is telling a different story from the one audiences know. The card explains that generations ago, the Kollu first preyed on the people, and that the truth was hidden inside a gentler tale meant for children to carry. The Kollu are not explained beyond that message.

Bill Skarsgård does not appear, which makes sense given how far back the story reaches. Instead, the special focuses on the early history of the land and on the people who first faced the horror lurking beneath it.

‘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. https://t.co/0gVYCbSn6T

— DiscussingFilm (@DiscussingFilm) October 31, 2026

The episode takes place before the events of the series’ fourth episode, which explained why IT cannot leave Derry. In that sense, it works as a companion piece that fills in the backstory behind one of the show’s central mythology points.

One of its biggest reveals involves the Indigenous warrior who created the dagger that frightens IT. That character is played by Zahn McClarnon, and the special finally gives the weapon an origin.

The special also nods to Stephen King lore by mentioning Maturin, the cosmic avatar of order said to have battled IT for millennia, and it includes a brief glimpse of him. For longtime readers of the novel, that connection is a significant treat.

Tazbah Chavez directed the special, and Cherie DiMaline and Jasmyne Flournoy wrote it. The cast includes Kimberly Guerrero, Kiawentiio, Morningstar Angeline, Isabel Deroy-Olson, Michael Podemski-Bedard, Thosh Collins and McClarnon.

That creative team centers Indigenous voices in a story about the land’s oldest history, which fits the way the series has used Derry’s past to explore the town’s curse.

The special lands at an important moment for the franchise. HBO announced in August that ‘IT: Welcome to Derry’ will return for a second season, and it is set to jump back to 1935 during the Great Depression.

Season 1 was set in 1962, 27 years before the ‘IT’ films’ first timeline, and the new season continues the show’s backward-in-time structure. Showrunner Brad Caleb Kane has teased a version of Pennywise unlike anything seen before, and he has said the writers are partway through the scripts.

A surprise special that digs even deeper into the legend helps keep momentum going while fans wait for new episodes. It also hints at where the series might look next, as the Muschiettis have previously suggested that later seasons could explore earlier feeding cycles in IT’s pattern of waking every 27 years.

Fans online have embraced the release as a perfect Halloween treat. One viewer joked that dropping an origin story on October 31 is the most Pennywise move possible, since Derry seems to have been cursed long before it had a zip code.

For those who want to dive in, the special is available to stream on HBO Max alongside the first season. The first season has 8 episodes and follows the events of 1962, so the special serves as a short, spooky detour into a much older era.

Whether the Kollu will return in the second season remains to be seen. For now, ‘A Story of Derry’ offers a compact piece of mythology that adds new texture to the series’ version of Derry.

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