HBO Max has given horror fans an unexpected Halloween treat, releasing a surprise new episode of IT: Welcome to Derry on Saturday 31 October 2026. Titled “A Story of Derry”, the 30-minute special takes viewers hundreds of years into the town’s past, exploring the ancient evil that existed long before Pennywise became its most recognisable face. The episode is now streaming on HBO Max, with the release arriving without any advance announcement.
The special follows three youngsters who venture into the Western Wood, where they encounter a terrifying ancient spirit. Set centuries before the events of the main series, the story explores an earlier chapter in Derry’s history and the origins of the supernatural presence that has haunted the town for generations.
HBO Max announced the surprise release on social media, teasing the episode as a Halloween treat alongside a short clip showing a young Indigenous girl running through the woods with a bow and arrow. The special is directed by Tazbah Chavez and written by Cherie Dimaline and Jasmyne Flournoy, with a cast including Kiawentiio, Zahn McClarnon and Isabel Deroy-Olson.
The original IT: Welcome to Derry premiered in October 2025 as a prequel to Andy Muschietti’s IT films, which were released in 2017 and 2019. Set in Stephen King’s fictional town of Derry, the series explores the history of the evil entity associated with Pennywise, played by Bill Skarsgård, and the horrifying events that have shaped the town over the years.
What Do We Know About IT: Welcome to Derry Season 2?
The Halloween surprise comes as work continues on the show’s second season, which has already been confirmed by HBO. The next chapter will take viewers back to 1935 during the Great Depression, focusing on the Bradley Gang massacre, an event referenced in Stephen King’s original novel.
Showrunner Brad Caleb Kane recently confirmed that writing is underway and that the production is moving forward, with plans to explore another period in Derry’s troubled history. He has also teased a different portrayal of Pennywise, with Bill Skarsgård expected to return to the role. An official release date for season two has not yet been announced.
For CultureCues, what a brilliant little Halloween surprise! We love when a show drops something unexpected, especially on a day when everyone is already in the mood for a good scare. IT: Welcome to Derry has plenty of horrifying history left to explore, so getting another story from the town’s past ahead of season two is a lovely treat for horror fans. And really, what better way to spend Halloween than voluntarily heading back to Derry? Although we certainly wouldn’t recommend visiting in person.
“A Story of Derry” is now streaming on HBO Max, which is also available in the UK through eligible NOW Entertainment & HBO Max memberships.
More From CultureCues
Netflix Pride and Prejudice Official Trailer: Emma Corrin and Jack Lowden Lead New Adaptation
The Jigsaw Puzzle Murder: Paramount+ Releases Trailer for New British True Crime Documentary
SweetPea Season 2 Trailer: Ella Purnell Returns as Sky Confirms November Release Date
Nikki Murray is a UK-based writer, screenwriter and founder & editor of CultureCues, covering film, television, music and pop culture. Her work focuses on storytelling and the moments shaping modern entertainment.