‘It: Welcome to Derry’ Drops a Surprise Halloween Special Set Hundreds of Years Before Pennywise

Updated

A scene from the HBO Max series It: Welcome to Derry

“It: Welcome to Derry” has a new 30-minute special on HBO Max, and it reaches hundreds of years into the town’s past. Released today for Halloween, “A Story of Derry” takes place long before the series’ events and Pennywise’s introduction.

A scene from the HBO Max series It: Welcome to Derry
A scene from “It: Welcome to Derry,” the HBO Max prequel series set in the haunted town of Derry, Maine. (It: Welcome to Derry)

The Stephen King adaptation debuted on October 26, 2025, expanding the world of the 2017 and 2019 “It” films as a prequel. Its 1st season follows residents of Derry, Maine, in 1962 as they encounter the shape-shifting evil that appears as Pennywise.

A scene from the HBO Max series It: Welcome to Derry
A scene from “It: Welcome to Derry,” the HBO Max prequel series set in the haunted town of Derry, Maine. (It: Welcome to Derry)

HBO renewed the series in August. Season 2 will move back to 1935, during the Great Depression, with a story built around the Bradley Gang massacre, an episode from King’s novel. The bank robbers arrive in Derry to purchase ammunition and encounter horror there.

Co-creator Andy Muschietti said in August, before the renewal announcement, that the Season 2 writers’ room was already open. He described a town worn down by poverty and unemployment, with a new group of children that includes orphans and runaways.

“They’re in a very different situation. Some of them are orphans or runaways, and so the environment is pretty bleak,” Muschietti said. “But there’s always the aspect of hope that is always there, burning, and it’s what keeps our new group going.”

Meet the author

Chrissy Stockton

Chrissy is the co-founder of Creepy Catalog. She has over 10 years of experience writing about horror, a degree in philosophy and Reiki level II certification.