HBO Max Drops Surprise Halloween Episode of 'It: Welcome to Derry'

HBO Max released a surprise 30-minute episode of "It: Welcome to Derry" on Halloween, titled "A Story of Derry." The special is set hundreds of years before the series' events and before the introduction of Pennywise, the shape-shifting clown at the center of the franchise.

The stealth drop lands at a busy moment for the supernatural horror. HBO renewed the show for a second season in August, and "It: Welcome to Derry" premiered on HBO Max on Oct. 26, 2025. The series is based on Stephen King's novel "It" and builds on the two-part film reboot from 2017 and 2019. It serves as a prequel to those films.

What do we know about Season 2?

Season 1 is set in 1962 in the fictional town of Derry, Maine, and follows residents' earlier encounters with Pennywise. Season 2 jumps further back, to 1935, during the Great Depression.

Per the logline, the new season "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 appears as one of the interludes in King's original novel.

Co-creator Andy Muschietti told Variety, before the renewal was announced, that the writers' room had already opened for Season 2. He sketched the mood in concrete terms.

"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."

How will the show's look change?

Muschietti also confirmed Season 2 will carry a different aesthetic from Season 1. His description is blunt.

"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."

So the pattern is clear: one season per era, each digging deeper into Derry's rotten history. With a Halloween special reaching back centuries and Season 2 heading to 1935, the franchise keeps widening the wound. King's interludes give it plenty of material to mine.