Pennywise Returns in the New “IT: Welcome to Derry” Midseason Trailer

Welcomt to Derry - Bill Skarsgard

November 17, 2025

Written by Kelli Marchman McNeely

Kelli Marchman McNeely is the owner of HorrorFuel.com. She is an Executive Producer of "13 Slays Till Christmas" which is out on Digital and DVD and now streaming on Tubi. She has several other films in the works. Kelli is an animal lover and a true horror addict since the age of 9 when she saw Friday the 13th. Email: horrorfuelinfo@gmail.com

After several weeks of terrifying buildup, the infamous red balloon has finally surfaced. HBO Max has unleashed the midseason trailer for the hit horror series “IT: Welcome to Derry.” It gives us the first full glimpse of the notorious Pennywise the Dancing Clown, teasing his readiness to show his painted face and commence his feast.

The trailer features the shapeshifting entity’s most iconic form, with Bill Skarsgård returning. Watch as he delivers the chilling line, “I’ve always wondered how you’d taste.” You will also see things from IT: Chapter One. There are also easter eggs and nods to the King Universe. That includes a mist descending over Derry, a bus labeled Shawshank State Prison. We see Lilly looking at pictures featured in IT: Chapter Two, and the rundown house where the Losers Club battled Pennywise in the movies.

The show’s debut season is four episodes deep and there are four more yet to air. HBO Max has now dropped the midseason trailer teasing the heightened terror that awaits viewers in the coming weeks. While the first half of the season focused on different nightmarish forms the entity takes, it also establishes the characters. Now, the latter half promises to bring Pennywise himself to the forefront.

“IT: Welcome to Derry” serves as an expansion of Andy Muschietti’s cinematic universe, which is based on Stephen King’s iconic 1986 novel. The first season is set in 1962. It chronicles the events that will eventually lead up to the 2017 film It: Chapter One.  to ensure continuity and style, Muschietti himself directed multiple episodes.

The series takes inspiration from Mike Hanlon’s interludes from King’s original book, which document the “catastrophic events.” IT tales of the dark history of Derry, Maine. Word is, producers are already making plans for more seasons. The seasons will happen in their own distinct historical eras, further charting the supernatural history of the town.

Last night, in Episode 104, dark truths came to light including how the native Americans first delt with “IT.” We also saw a child lose an eye and uncovered what Hank has been hiding and his reason for not revealing his alibi. And Pennywise made his first brief appearance in the shadows in the Hanlon’s yard after Will nearly drowned.

Let the midseason trailer whet your appetite for a serious taste of terror as Pennywise gets ready to feast. Watch the first four episodes now.

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