You probably remember exactly where you were when you first saw the bus. The big, orange, skeletal-driven bus that hauled Marnie Piper away from her boring mortal life and into a world where being "weird" was just Tuesday. Honestly, for a lot of us, the Halloweentown franchise isn't just a series of Disney Channel Original Movies (DCOMS); it’s the definitive mood of October.
But if you’re planning a marathon, you’ve gotta do it right. Following the halloweentown movies in order isn't just about chronology. It's about watching a family legacy grow, seeing the special effects get progressively more "early 2000s," and eventually hitting that massive bump in the road where the lead actress suddenly changes.
Let's break down the timeline, the lore, and why that final movie still feels like a glitch in the Matrix.
The Cromwell Saga: Halloweentown Movies in Order
Watching these in the order they were released is the only way that makes sense. You need to see Marnie go from a frustrated teen who isn't allowed to go to a Halloween party to a college student grappling with ancient prophecies.
1. Halloweentown (1998)
This is the blueprint. Directed by Duwayne Dunham, the first film introduced us to Marnie Piper (Kimberly J. Brown), her uptight mom Gwen (Judith Hoag), and the legendary Debbie Reynolds as Grandma Aggie.
The plot is basically every kid's dream. Marnie finds out she's a witch on her 13th birthday, sneaks onto a magical bus, and discovers a town where monsters live normal lives. They go to the dentist. They have gyms. It's cozy horror at its best. The villain, Kalabar, is a classic "scorned ex" archetype who wants to take over the mortal world because he's bitter.
The most iconic thing about this movie? The giant jack-o'-lantern in the town square. It’s real, by the way. St. Helens, Oregon, where they filmed, still sets it up every year.
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2. Halloweentown II: Kalabar’s Revenge (2001)
Three years later, things got a lot darker. Literally. The "Grey Spell" is a genuinely creepy concept for a Disney movie. A warlock named Kal (Kalabar's son, played by Daniel Kountz) turns Halloweentown into a monochrome, boring version of the human world, while turning humans into monsters.
This sequel is often cited as the fan favorite because the stakes feel higher. Marnie isn't just a trainee anymore; she’s the one leading the charge. Also, can we talk about Gort’s house? The lost and found of the universe? It was peak imaginative set design for a TV budget.
3. Halloweentown High (2004)
By 2004, Disney wanted to lean into the high school musical/drama vibe that was taking over the network. Marnie convinces the Halloweentown Council to let a group of "monster" students attend her mortal high school as part of an exchange program.
It’s a bit cheesier than the first two, but it has heart. It tackles themes of prejudice and "fitting in" through the lens of trolls and ogres wearing human masks. This was also the last time we saw the original "Marnie" in the role, which makes it a bittersweet watch for the purists.
4. Return to Halloweentown (2006)
The final installment. Marnie heads to "Witch University," but something is... off. Specifically, Marnie's face.
Disney recast Kimberly J. Brown with Sara Paxton. To this day, fans argue about this more than the actual plot. The story involves a secret prophecy about "The Gift" and a sinister group called the Dominion. It’s a fine movie on its own, but for many, it just didn't feel like the same series.
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The Recasting Drama: What Actually Happened?
Look, Sara Paxton is a great actress. She was fantastic in Aquamarine. But replacing the lead of a franchise in the fourth movie is a bold, and usually bad, move.
For years, rumors swirled. Was Kimberly J. Brown busy? Did she have a scheduling conflict?
Nope. In several interviews over the years, Brown has been pretty transparent: she was available and wanted to do it. The decision was purely a Disney executive choice. Producer Sheri Singer eventually mentioned in 2024 that contract negotiations simply didn't work out. Apparently, there were "unusual perks" and salary requests that Disney wasn't willing to meet.
It’s a classic Hollywood "business" ending to a very magical story. It's why many fans treat the first three as a trilogy and the fourth as a spin-off.
Why the First Movie Still Works in 2026
Even with the dated CGI—remember the flying broomstick scenes?—the 1998 original holds up. Why? Because of Debbie Reynolds.
She didn't treat it like "just a kids' movie." She brought a theatrical, grand energy to Aggie Cromwell that made the world feel lived-in. When she tells Marnie, "Being normal is vastly underrated," she isn't just reading a line. She’s delivering the thesis statement of the entire franchise.
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Then there's the setting. St. Helens, Oregon, wasn't a soundstage. It was a real town with real streets, and that groundedness is something modern, green-screen-heavy movies often miss. You can actually feel the October chill in those frames.
Quick Stats for the Super-Fans:
- Budget: The first movie was made for about $4 million.
- Filming Location: St. Helens, Oregon (the town square is basically identical today).
- Ratings: Return to Halloweentown actually had the highest viewership at the time, with 7.5 million viewers, despite the backlash.
- Cast Fact: Judith Hoag (the mom) was the original April O'Neil in the 1990 Teenage Mutant Ninja Turtles.
How to Watch Them Now
You can find all the halloweentown movies in order on Disney+. If you’re a physical media collector, the DVDs are getting harder to find but are worth it for the nostalgic menus.
If you really want the full experience, take a trip to St. Helens in October. They host the "Spirit of Halloweentown" festival. They light the pumpkin, there are costume contests, and occasionally, members of the original cast show up to sign autographs.
Pro tip: Start your marathon at 7:00 PM on a Friday. By the time you get to the fourth movie, you’ll be tired enough that the recast won't hurt quite as much.
Actionable Insights for Your Next Rewatch:
- Look for the cameos: Keep an eye out for Lucas Grabeel (Ryan from High School Musical) in the later films.
- Spot the "Benny" change: The skeleton taxi driver is iconic, but his voice actor actually changed between the first and second movies.
- Pay attention to the Cromwell colors: Notice how the purple and velvet aesthetic of the family's clothing evolves as their magic gets stronger.
The legacy of these films isn't in their special effects or their complex plots. It's in that feeling of belonging. Whether you're a witch, a warlock, or just a kid who doesn't quite fit in at school, Halloweentown always has a seat on the bus for you.
To get the most out of your nostalgia trip, check the "Spirit of Halloweentown" official festival schedule online before you plan a trip to Oregon, as ticketed events often sell out months in advance.