Organization: Conner Prairie
Role: Creative Director / Experience Developer
Completed: 2024
Status: Built / Ongoing
Key Contributions: Creative Direction | Concept Development | Experience Development | Media Programming | Special Effects | Operational Planning
The Opportunity
The Headless Horseman Hayride debuted at Conner Prairie in 1983 and has been a fall tradition ever since. What began as a single haunted hayride gradually grew into the larger Headless Horseman Festival, with additional activities and entertainment giving guests more to experience before and after their scheduled ride. Through all of those changes, the hayride remained the centerpiece of the event.
Over time, however, the ride itself had moved away from the story that originally inspired it. An encounter with the Headless Horseman was still the finale, but the rest of the route had become populated with familiar Halloween elements including witches, ghosts, skeletons, zombies, and spiders, with little connecting them to one another or to The Legend of Sleepy Hollow.
When I assumed leadership of Conner Prairie’s Festivals & Events team in 2024, I saw an opportunity to refocus the attraction around the story of Ichabod Crane. For the first time, the entire hayride would tell a version of The Legend of Sleepy Hollow, using the journey itself to draw guests into the story and build toward Ichabod’s encounter with the Headless Horseman.
My Role & Approach
I served as creative director and experience developer for the reimagined hayride, establishing the overall direction and leading the team in rebuilding the experience around the story of Ichabod Crane. We developed a new script for the entire ride, redesigned scenes along the route to support the story, created a pre-show video to establish the setting before guests boarded, and added new special effects for key moments.
I also served as the ride programmer, programming new GPS-triggered media players and testing and adjusting the trigger points so that individual audio tracks aligned with scenes along the route. I developed the trigger system for the pre-show video and created timing models to evaluate ride capacity and guest flow.
The project was a collaborative effort, with members of the team contributing to script development, filming, audio recording, costumes, and scenic installation.
The Experience
The reimagined hayride placed guests in the footsteps of Ichabod Crane as he made his journey home from the Van Tassel family’s party. Ichabod remained unseen for most of the ride, allowing guests to experience the journey from his perspective as the story shifted between third-person narration and his own thoughts.
Setting Up the Story
Before boarding the hayride, guests watched a short pre-show video that introduced Ichabod Crane, Katrina Van Tassel, and the events leading up to the journey they were about to take. This allowed the ride to begin as Ichabod left the Van Tassel home rather than spending the first part of the attraction establishing the characters and setting.
As the wagon departed, guests passed the Van Tassel house, where partygoers waved goodbye to Ichabod, before traveling through Tarrytown and past the schoolhouse where he taught.
Storytelling in Motion
The previous repeating soundtrack was replaced with a series of audio tracks written for specific portions of the route. As guests traveled farther from Tarrytown and deeper into the woods, the narration followed Ichabod’s journey and increasingly shifted into his own thoughts as his uneasiness grew.
GPS-triggered media players synchronized the audio with the physical environment. Guests passed an old graveyard where a shadowy figure could be seen in the woods before reaching their first encounter with the Headless Horseman. After the wagon escaped, the story continued deeper into the woods, eventually passing an encampment filled with the headless remains of the Horseman’s previous victims.
Bringing the Story to Life
The story eventually brought guests into Sleepy Hollow, where a bridge ahead represented their chance to escape. Before the wagon could reach it, the Headless Horseman appeared and blocked the road, forcing the wagon in another direction.
After circling back, the wagon made a second attempt for the bridge. The Horseman returned and gave chase as the wagon raced toward safety. As guests crossed, the bridge erupted in smoke and simulated flames and the Horseman disappeared behind them.
The Final Encounter
Washington Irving leaves Ichabod Crane’s fate uncertain, and the narration following the chase retained some of that ambiguity. Guests were told that no one really knew what happened to Ichabod after his encounter with the Horseman and that he was never seen again.
As the wagon rounded the final corner, it passed an old inn where ghostly figures appeared in the windows using a Pepper’s Ghost illusion. The wagon then stopped in front of the inn, where Ichabod appeared for the first time and assured guests that he had survived after all.
That reassurance didn’t last long. In the final moment of the ride, Ichabod’s head suddenly dropped from his shoulders into his hands. The scene went dark, revealing our answer to the question Irving had left unresolved.
Evolution & Results
Guest response to the reimagined hayride in 2024 was mixed. Guests responded positively to the stronger emphasis on storytelling, but some felt there was less to see along the route after many of the unrelated scenes from previous years had been removed. The new GPS-triggered media system worked as planned, but we also learned that portions of the experience relied too heavily on spoken narration, which could sometimes be difficult to hear over the tractor and other ambient noise.
We used that feedback to make further revisions for 2025. Additional scenes and scares were added while keeping them connected to the larger story, and the amount of narration was reduced. Guest response improved significantly, reinforcing the overall direction while helping us find a better balance between storytelling and the expectations guests bring to a haunted hayride.
The experience continues to evolve. For 2026, the story is being expanded to introduce the three Fates from Greek mythology — the Spinner, the Measurer, and the Cutter — whose intervention in Ichabod’s journey helps explain how his ultimate fate is determined.
Operational & Festival Impact
The new media system performed as designed, reliably triggering audio at specific points along the route. Timing models developed during planning also proved accurate, while changes to loading and unloading procedures helped reduce the time between dispatches and slightly increase ride throughput.
The hayride reimagining was part of a broader series of changes to the Headless Horseman Festival in 2024. We refreshed entertainment and other experiences, began creating a more cohesive identity across the event, and changed the ticketing model so that festival admission was no longer tied to the capacity of the hayride.
Those changes allowed guests to attend the festival without purchasing a hayride ticket and removed ride capacity as the limiting factor for overall event attendance. Festival revenue increased by approximately 58% in 2024, and we were able to sustain that higher level of revenue in subsequent years.