Surprise! ‘IT: Welcome to Derry’ Drops a New Halloween Special Exploring IT’s Origins

Holy shit. HBO Max had one more Halloween surprise waiting for us.

IT: Welcome to Derry has dropped a new, 30-minute special titled “A Story of Derry,” now streaming on HBO Max. Arriving overnight for Halloween, the episode travels hundreds of years before Pennywise to explore the ancient horror lurking in Derry.

According to TheWrap, the story follows three youngsters into the Western Wood, where they encounter a terrifying ancient spirit. HBO also released a trailer, which you can watch below.

HOLY SHIT! HBO Max just surprise-dropped a BRAND NEW ‘IT: Welcome to Derry’ special for HALLOWEEN! 🎈 Titled ‘A Story of Derry’, the 30-minute episode takes us hundreds of years before Pennywise to explore the origins of IT. No warning. No countdown. STREAMING RIGHT NOW! https://t.co/O6UdHSJvS3

— Brad Miska @ DREAD CENTRAL (@DreadCentral) October 31, 2026

And we’re already getting more Derry beyond this surprise: HBO officially renewed the series in August. Brad Caleb Kane will serve as the sole showrunner for Season 2, which moves back to 1935 and the Great Depression, centering on the Bradley Gang Massacre. A premiere date has not been announced.

The renewal announcement also offered a measure of the show’s success: HBO said Welcome to Derry ranked among the top four global series premieres in HBO Max history. That’s a launch ranking, rather than a total audience figure for the entire season.

IT was a cultural event, and we don’t get many of those. It’s fun to see this world continue expanding while Mike Flanagan is still developing The Dark Tower. There’s no announced crossover between the productions, but imagining those corners of Stephen King’s universe sharing a world is part of the fun.