On Halloween 2026, HBO Max gave horror fans an unexpected treat. At midnight on Saturday, October 31, the streamer released a brand-new 30-minute IT: Welcome to Derry special called "A Story of Derry", with no advance warning. Searches for the show jumped sharply across the US within hours, with the strongest interest in Maryland, Maine, Rhode Island, West Virginia, and New Hampshire.
Quick Facts
- Title: A Story of Derry (Welcome to Derry Halloween special)
- Released: Midnight, Saturday, October 31, 2026
- Runtime: About 30 minutes
- Where to watch: HBO Max (US)
- Setting: Hundreds of years before Pennywise
- Season 2: Confirmed, set in 1935, no premiere date yet
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| A Story of Derry takes viewers back to the Western Wood, long before Derry existed |
Table of Contents
- What Is "A Story of Derry"?
- Cast and Crew
- How It Connects to the Series Lore
- Ending and What It Means
- Can Pennywise Time Travel?
- Pennywise's True Form
- Where to Watch
- Season 2 Update
- What About Season 3?
- Frequently Asked Questions
What Is "A Story of Derry"?
"A Story of Derry" is a standalone special, not part of Season 1's eight-episode run. It is set hundreds of years before Pennywise's 1962 storyline. The official description follows three young people who venture into the Western Wood and encounter a terrifying ancient spirit.
Fans looking for the clown should adjust expectations. The story centers on the Indigenous community that first confronted the evil in the land that would later become Derry, Maine, and the special serves as an origin-style chapter for the show's mythology.
Cast and Crew
The special brings back the Indigenous cast from Season 1 and adds a well-known name.
| Role | Name |
|---|---|
| Young Rose | Kimberly Guerrero |
| Sesqui | Morningstar Angeline |
| Necani | Kiawentiio |
| Added to the cast | Zahn McClarnon |
| Director | Tazbah Chavez |
| Writers | Cherie Dimaline and Jasmyne Flournoy |
How It Connects to the Series Lore
Season 1, Episode 4 introduced the legend of the "monster in the Western Wood" and the Shokopiwah, the Indigenous people who learned to contain it. In that lore, they used fragments of a meteor tied to the creature's origin to create a barrier that kept it confined to the woods, the same land that later became Derry.
"A Story of Derry" appears to dramatize that foundation. Early coverage describes it as an exploration of IT's origins in Derry.
The Maturin Connection
Some reports say the special also brings in Maturin the Turtle, the benevolent cosmic being from Stephen King's novel who stands as a counterweight to IT. Season 1 had already planted the seeds: the "Children of Maturin" are Rose's community, and in the finale she gives Dick Hallorann a Maturin-root tea to help him connect with IT.
Ending and What It Means
Without spoiling the special, the key takeaway is that it expands the mythology backward. It shows that the threat in Derry long predates the town and the cycle of killings Pennywise is known for. That fits the show's larger plan to move further back in time with each season.
Can Pennywise Time Travel?
Not as far as the series has shown. IT is portrayed as an ancient, ageless entity that has existed in the same place for millions of years, feeding in roughly 27-year cycles. The show jumps between eras because the storytelling moves through time, not because Pennywise does. Season 1's finale does use Dick Hallorann's psychic abilities to track IT across time, but that is a human power, not a Pennywise one.
What Is Pennywise's True Form?
In Stephen King's story, Pennywise is just one disguise worn by a cosmic entity from beyond our universe, one that takes whatever shape best feeds on fear. The show leans into this idea: in the Season 1 finale, IT cycles through several forms before retreating into raw deadlight. The special's pre-Pennywise setting reinforces that the clown is a mask, not the creature itself.
Where to Watch "A Story of Derry"
IT: Welcome to Derry, including the new special, streams on HBO Max in the US. Season 1's eight episodes are available there too, so you can catch up before or after the special.
Is Welcome to Derry Season 2 Confirmed?
Yes. HBO officially renewed the series on August 17, 2026. Here is what we know so far:
- Setting: 1935, during the Great Depression
- Story focus: The infamous Bradley Gang massacre, following a group of bank robbers who end up in Derry
- Tone: Co-creator Andy Muschietti has described a very different feel from Season 1, with a poor, depleted Derry and a gangster-movie flavor for IT
- Showrunner: Brad Caleb Kane, now the sole showrunner
- Executive producers: Andy and Barbara Muschietti, with Kane, Roy Lee, Dan Lin, Jamie Travis, and Dhana Gilbert
Season 2 Release Date and Filming Status
No premiere date has been announced. The show is reportedly still in pre-production, with scripts about halfway done. Kane has indicated that filming is expected to begin around summer 2027, pointing to a late 2027 or 2028 release. Treat that as an estimate, not a confirmed schedule.
What About Season 3?
The creators have planned a three-season arc, with each season going further back in time. Season 3 has not been officially greenlit.
| Season | Year | Focus | Status |
|---|---|---|---|
| Season 1 | 1962 | Black Spot massacre, the Hanlon family | Released |
| Season 2 | 1935 | Bradley Gang era | Renewed, in development |
| Season 3 | 1908 | Early Derry and Pennywise's origins | Planned, not confirmed |
Frequently Asked Questions
Is "A Story of Derry" a new episode of Season 1?
No. It is a standalone Halloween special set hundreds of years before the Season 1 events.
How long is "A Story of Derry"?
The special runs about 30 minutes.
Does Pennywise appear in the special?
The story is set before the Pennywise era and centers on an ancient spirit and the Indigenous community that first faced it.
Do I need to watch Season 1 first?
The special stands on its own, but it is richer if you have seen Episode 4 and the finale.
Is Welcome to Derry connected to the IT movies?
Yes. It is a prequel to the 2017 and 2019 films, set 27 years before the events of IT Chapter One.
When does Welcome to Derry Season 2 come out?
There is no official date yet. Reported filming plans point to a late 2027 or 2028 release, but that is unconfirmed.
Is Welcome to Derry good?
The series has been received as a mixed-to-positive watch, with an 81% Rotten Tomatoes score and a 7.9/10 rating on IMDb at the time of writing.
Details in this article reflect reporting available on October 31, 2026, and may be updated as more information about the special and Season 2 is released.
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