‘It: Welcome to Derry’ Surprise Halloween Episode Drops on HBO Max

Just in time for the spooky holiday, HBO has released a surprise episode of “It: Welcome to Derry” on the streaming platform. Titled “A Story of Derry,” the special comes in at 30 minutes and is set hundreds of years before the show’s events and the introduction of Pennywise.

The timing is perfect for a surprise release of the supernatural horror, which HBO renewed for a second season in August. “It: Welcome to Derry” originally premiered on HBO Max on Oct. 26, 2025. It is based on Stephen King’s novel “It” and builds on the two-part “It” film reboot from 2017 and 2019. The show serves as a prequel to the films.

That month, before the show’s official renewal was announced, co-creator Andy Muschietti told Variety that the writers’ room had opened for Season 2. “There’s gonna be a lot of that depression-era hustling in the air in our characters. Everybody’s trying to get by and survive the circumstances. They are gonna do crazy things,” Muschietti said. “And of course, the social, cultural, horrible things that were happening in the era, too. We’re not going to skip those. [They are the] very center and the heart of our story.”

He also clarified that Season 2 will have a different aesthetic than Season 1.

“In this case, on the surface, Derry is a graveyard almost. It’s a carcass of something because people are depleted, poor, tired, jobless, homeless. The kids don’t have a suburban, comforting life,” Muschietti said. “They’re in a very different situation. Some of them are orphans or runaways, and so the environment is pretty bleak. But there’s always the aspect of hope that is always there, burning, and it’s what keeps our new group going.”

Season 1 is set in 1962 in the fictional town of Derry, Maine, and details the town’s residents’ earlier experiences with the evil, shape-shifting clown, Pennywise. Season 2 will do back in time to 1935 and takes place during the Great Depression. Per the logline, the story “centers on the bloody massacre of the Bradley Gang, a group of bank robbers who stop in Derry to buy ammo and end up facing unimaginable horror.” (The Bradley Gang Massacre is one of the interludes in King’s original novel.)