Since debuting in 1998, Disney’s Halloweentown has spawned a total of four films and at least one marriage (co-stars Kimberly J. Brown and Daniel Kountz of Halloweentown II: Kalabar’s Revenge). It’s developed quite the fanbase since the original Halloweentown, turning the town of St. Helens, Oregon, into a tourist location, specifically in October when the town embraces its cinematic connection for a monthlong “Spirit of Halloweentown” event. Currently on the festival circuit and screening during The Overlook Film Festival 2025 is co-directors Bradford Thomason and Brett Whitcomb’s documentary The Spirit of Halloweentown, a three-prong exploration of the St. Helens community, their celebration, and their relationship to the film.
A still from the documentary THE SPIRIT OF HALLOWEENTOWN. Photo courtesy of Window Pictures.
Across the four weeks leading up to Halloween 2023, Thomason and Whitcomb chat with a variety of members of the St. Helens community (business members, Halloweentown organizers, community members) to get a sense of what the town is like during this seasonal event. Through their conversations and captured footage, personal feelings are shared, revelations about the town’s potentially haunted locations are explored, and the notion of legacy is examined. Not everyone in St. Helens enjoys the event and not everyone enjoys outsiders coming into their town (as guests or to set up shop), resulting in moments that convey an undercurrent of dissatisfaction amidst the excess celebration that others enjoy. Strangely, as a result, Halloweentown comes across as disjointed and unfocused on a singular notion, remaining interesting solely for its individual fragments whose narrative tethers don’t quite coalescence into a singular story.
A still from the documentary THE SPIRIT OF HALLOWEENTOWN. Photo courtesy of Window Pictures/The Overlook Film Festival.
After a brief intro to the city, the directors smartly open the film by first stopping in at the city hall, a structure that is used within the Halloweentown films. This not only provides a physical anchor between the film and the documentary and the month-long event, it also helps open the door to more supernatural elements that will be explored. Thankfully, even those who haven’t seen the Halloweentown films are given a bit of information in both this sequence and another so that viewers understand how city hall plays into things. From here, however, is where things get a bit more difficult regardless of whether you’re familiar with the films or not as Thomason and Whitcomb start jumping between different locals who will become our respective guides for the four-week period leading up to Halloween and the lighting of Jack, a jack-o-lantern structure in the center of town. The difficulty comes from the fact that none of the individuals we meet are given any kind of placard when they appear identifying their name and relationship to the town (as appropriate), a tactic used in many documentaries to help the audience know who they are observing, regardless of whether it’s mentioned in the scene or not. As such, the documentary more often feels like we’re thrown into St. Helens and are expected to keep up with the conversation.
This doesn’t matter as much with the person working in City Hall who provides the brief explanation of the town and overtly ducks any discussion of the supernatural on camera because we never come back to that person. But the business owner who walks us through a few businesses they own (haunted house, alien exhibit), the former cheerleader working with the local high school cheer squad to present a Halloween-themed cheer presentation, the out-of-towner who bought a local restaurant and is revamping it, the woman behind “Spirit of Halloweentown” — these people are who we spend the most time with (the last three especially) and we are never shown their names, they’re only brought up in conversation. By missing who they are, it often feels like there’s this wall between us, making information the documentary seems to want us to have inaccessible. Especially when the film transitions to the paranormal expert and the lone presented “Halloweentown” dissenter, knowing who these people are matters as it helps humanize them further and make their respective stories matter to the audience receiving them. Even the St. Helens resident who has a confused understanding of Halloween’s origins (Celtic, not Satanic, ma’am) is compelling as their misconception relates to the local belief in Heaven, Hell, and the supernatural. Yet, within the context of everything else, it lacks as much impact as it seeks to make.
A still from the documentary THE SPIRIT OF HALLOWEENTOWN. Photo courtesy of Window Pictures.
Truly, while one would think that the film would center the maker of the event, it tends to lean more toward the new business owner who flubbed hard with the locals and whose business is possibly haunted (thereby creating the opportunity to introduce the paranormal investigators) and the former cheerleader. Both stories are interesting, yet only one (the cheerleader) is given any kind of seemingly complete narrative through the presentation of the film. Oddly, not even the inclusion of the paranormal investigator brings about any excitement or, frankly, increased plausibility to supernatural entities or forces. The inclusion often appears abruptly and not as the result of some kind of transition in the material shown just prior, but as an element extending off a need to continue the conversation about the spooky and ooky. (Within the last five years, someone via TikTok or Instagram Reels posted a video commenting on the lack of vengeful Indigenous or African spirits in the United States seeking revenge for all that was done to them and, honestly, that put me off the idea that spirits might be real.)
A still from the documentary THE SPIRIT OF HALLOWEENTOWN. Photo courtesy of Window Pictures/The Overlook Film Festival.
One thing that the film does well is convey the notion of legacy and the curation of what we pass down, whether it be the belief in a higher power, a life beyond this one, or a Disney Channel movie we loved in our youth. When seeing the response of the Halloweentown attendees — the joy on their faces, the costumes, the events, the community — one does take away a sense that what Spirit of Halloweentown does matters, not just as a financial boon for local businesses, but in carving out a space for happiness at a time and moment when that can be hard. It’s difficult to say whether fans of the films will take more from this as the various transitional shots of structures and locations lack meaning to someone such as myself without such a background, but this is where a reliance on institutional knowledge of the Halloweentown films by the filmmakers would really help open this up for others. Even something as simple as a placard can make a massive difference for the audience seeing the forest for the trees.
Screened during The Overlook Film Festival 2025.
Available on Amazon, Apple TV, and YouTube October 24th, 2025.
For more information, head to the official Window Pictures The Spirit of Halloweentown webpage.
Final Score: 3 out of 5.
Share this:
Categories: In Theaters, Reviews
Leave a Reply