'It: Welcome to Derry' Drops a Surprise Episode Set Before Pennywise

The 30-minute special, “A Story of Derry,” sends three young people into the Western Wood, where they meet an ancient spirit.

In a short Instagram clip HBO Max posted for Halloween, a Native American girl races between the trees, her bow and arrow held ready. It's the tease for a surprise episode of “It: Welcome to Derry” set hundreds of years before Pennywise.

The 30-minute special, called “A Story of Derry,” went up on HBO Max, Variety reported. In its post, the streamer pitched it as a never-before-seen look at where IT came from in Derry. Deadline reported the logline: three young people head into the Western Wood, where they run into a terrifying ancient spirit.

Going back that far isn't a one-off. It's how this prequel works. The first season took place in 1962 in Derry, Maine, the made-up town where the shape-shifting clown hunts, Variety noted. Season 2 moves back to 1935, in the middle of the Great Depression.

That season is built around the Bradley Gang, bank robbers who pull into Derry to buy ammunition and run into horror they can't imagine, Deadline reported. Their massacre is one of the history chapters Stephen King tucked into his 1986 novel. The Halloween special leaves both of those decades behind by centuries.

Season 2 is real, just not close. Showrunner Brad Caleb Kane told Deadline in October that the writers were about halfway through the scripts, the season was greenlit with a production schedule, and Andy Muschietti was out casting. Kane also promised Pennywise, played by Bill Skarsgård, shown in a “way you've never seen that character before.”

Muschietti, the show's co-creator, has described a town worn all the way down. Before HBO announced the renewal in August, he told Variety that the 1935 Derry would be full of broke, worn-out, jobless people and kids without comfortable homes. “Derry is a graveyard almost,” he said.

That's why a surprise half hour matters. The series premiered on HBO Max on Oct. 26, 2025, as a prequel to the 2017 and 2019 “It” films. Deadline says the next season is expected in late 2027 or 2028.

Until then, the newest look at Derry doesn't include a clown. It's a girl in the woods with a bow, hundreds of years before the town learned his name.

Source: Deadline, retrieved November 1, 2026. Other sources: Variety.