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

HBO has released a surprise episode of “It: Welcome to Derry” on HBO Max, just in time for Halloween. Titled “A Story of Derry,” the special runs 30 minutes and is set hundreds of years before the events of the series and the introduction of Pennywise. According to Variety, it arrived on the streamer at midnight on Saturday.

Based on Stephen King’s novel “It,” the series builds on the two-part “It” film reboot from 2017 and 2019 and serves as a prequel to those films. It premiered on HBO Max on October 26, 2025, and HBO renewed it for a second season in August.

Season 1 is set in 1962 in the fictional town of Derry, Maine. Season 2 will jump back to 1935, during the Great Depression. Per the official logline, it “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.

Co-creator Andy Muschietti told Variety the new season will have a different look from the first. “On the surface, Derry is a graveyard almost,” he said. “People are depleted, poor, tired, jobless, homeless.”

Sources: Variety