Pennywise Returns: Welcome to Derry Season 1 Release Date, Cast, Plot, and Everything You Need to Know
Derry calls again: HBO Max’s IT: Welcome to Derry arrives October 26, 2025, plunging deeper into Stephen King’s chilling universe with a prequel to the It blockbusters.
Pennywise is clocking back in. HBO Max is rolling out IT: Welcome to Derry, a prequel series to the recent It films that digs into the town’s history, trauma, and sewer system. It’s set earlier, it’s meaner, and yes, Bill Skarsgard is back under the greasepaint.
Release date, episode count, and the big-picture plan
Season 1 of IT: Welcome to Derry premieres October 26, 2025 on HBO Max in the US. The first season runs nine episodes and is designed as part one of a three-season arc, with each season jumping to a different era in Derry’s cursed timeline. Production started in May 2023 and wrapped in August 2024 after navigating the industry strikes, so this one’s been in the pipe for a while.
Where this sits in King’s world
The show plants us in 1962, 27 years before the 2017 It movie. A couple and their son arrive in Derry just as a young boy goes missing, and the town’s familiar rot starts bubbling up. That means the usual: unexplained disappearances, that nagging question about what the sewers are hiding, and kids being forced to stare down an evil adults refuse to see.
Underneath the supernatural, the series is also tackling real-world ugliness from the period. Expect racial tension and community-wide denial to factor in, including a dramatization of the burning of the Black Spot nightclub — a pivotal incident from Stephen King’s novel that the show is bringing to the forefront. Inside baseball alert: Chris Chalk is playing Dick Hallorann, the same Dick Hallorann from The Shining, which is a fun cross-thread for King readers.
The trailer vibe
HBO Max dropped the first trailer on September 23, 2025. It leans hard into dread: Pennywise lurking behind that red balloon, blood-smeared faces, kids screaming, and the lived-in 1960s setting stamped on every frame. The needle drop is 'Dreamers' by Joyce Harris, which gives the footage a deceptively sweet coating before the teeth come out.
Cast and who’s making it
- Bill Skarsgard as Pennywise
- Taylour Paige as Charlotte Hanlon
- Jovan Adepo as Leroy Hanlon
- Chris Chalk as Dick Hallorann
- James Remar
- Madeleine Stowe
- Rudy Mancuso
- Stephen Rider
Behind the scenes, Andy and Barbara Muschietti — the team that steered the It films — are executive producing, with Andy once again shepherding it to the screen. The show is produced by Double Dream (their company) and FiveTen Productions. Jason Fuchs and Brad Caleb Kane are the showrunners, and the executive producer roster also includes Bill Skarsgard, Shelley Meals, Lee and Dan Lin, and David Coatsworth.
What to expect in Season 1
New era, new kids, same nightmare cycle. The show is digging into Derry’s mythology and how the town keeps letting this happen. The central thread kicks off with that missing boy and a family walking straight into the grinder. On top of the supernatural scares, the 1962 backdrop means the human side of horror — prejudice, cover-ups, and communal amnesia — gets equal weight.
Bottom line: If you liked the movies but wanted more time in Derry’s past (and more connective tissue with King’s larger universe), this is that. The plan to do three seasons across three different time periods is a very 'let’s map the curse' swing, and I’m into it.