IT: Welcome to Derry Halloween special hints at season 2's dark secrets. Here's what we know

HBO Max has released a Halloween special titled A Story of Derry as part of its horror series IT: Welcome to Derry. The 30-minute episode premiered on October 31, 2026, and explores events set hundreds of years before the original IT story.

The special follows three youngsters who venture into the Western Wood, where they encounter an ancient spirit. Its release comes alongside the renewal of IT: Welcome to Derry for a second season, which is expected to explore more of the town's dark history.

Welcome to Derry serves as a prequel to the 2017 film IT and has attracted considerable attention, ranking among the top four series premieres in HBO Max history.


The show's executive producer, Sarah Aubrey, expressed excitement about returning to the fictional town, saying, "We are excited to return to the chilling world of Derry and to further expand on Andy and Barbara Muschietti’s horrifically iconic adaptation."

What is the plot of IT: Welcome to Derry's Halloween special?

Titled A Story of Derry, the 30-minute special takes viewers several centuries back in the town's history. It follows three young characters as they enter the Western Wood and encounter an ancient spirit.

Beyond its standalone storyline, the episode also offers potential clues about the mythology that will be explored in the upcoming season.

What to expect from IT: Welcome to Derry season 2?

The second season is expected to be set during the Great Depression in 1935. Its storyline will reportedly revolve around the Bradley Gang, a group of bank robbers whose encounter with Derry's supernatural horrors leads to a bloody massacre.

Showrunner Brad Caleb Kane has hinted that the new season will have a different visual style and tone.

"We’re making something very exciting for season 2 that I can’t talk too much about, but it’s got a different palette. It’s the Depression, it’s 1935," Kane said.

He further described the upcoming season as "a Warner Bros. gangster picture through the lens of Pennywise and Stephen King."

The new season is also expected to introduce several new characters, including children who could be runaways or orphans. Kane has further teased a fresh portrayal of Pennywise, suggesting that audiences will see the character in a way they have never experienced before.

Stephen King's grandson joins season 2 writers' room

HBO Max has also revealed that Ethan King, the grandson of author Stephen King, is joining the writers' room for the second season.

Meanwhile, the series has introduced Maturin the Turtle, a benevolent cosmic entity from King's fictional universe and one of Pennywise's greatest adversaries.

Its appearance in A Story of Derry could signal a deeper exploration of the mythology surrounding Pennywise and the supernatural forces connected to the town.

When will IT: Welcome to Derry season 2 be released?

The second season of IT: Welcome to Derry is still in development, with filming expected to begin in 2027. Although HBO Max has not announced a release date, Kane's comments suggest that the next instalment will take the story in a different direction.

The franchise is rooted in Stephen King's 1986 horror novel IT, which has inspired several adaptations over the years, including the 2017 film and its 2019 sequel.

With A Story of Derry expanding the town's supernatural history, the series is continuing to explore the origins of its horrors and the mythology surrounding its most iconic villain, Pennywise.