About This Festival

The Headless Horseman Festival at Conner Prairie in Fishers, Hamilton County, Indiana, is a seasonal fall event running Thursdays through Sundays from October 2 to October 26, 2025, from 5 p.m. to 10 p.m. It celebrates the legend of Sleepy Hollow with a mix of spooky and family-friendly activities, including a thrilling haunted hayride, an 11-acre haunted corn maze (Trail of Terror), live entertainment, plus themed food and drinks. The Apple Store at Conner Prairie is famous for its caramel apples and festive treats, making it a key stop during the festival[1][2][4][5][6].

The festival’s atmosphere blends mystery, folklore, and carnival fun amid the natural prairie setting. Guests journey into Sleepy Hollow’s story and encounter the Headless Horseman himself during the hayride, which travels through eerie woods with suspenseful surprises. The event is known for attention to detail with thematic decorations, music, and seasonal flavors such as hot cider, enhancing the autumn vibe[6].

Activities and Attractions:

  • Haunted Hayride: A tractor pulls wagons with guests over the dark prairie woods, culminating in an encounter with the Headless Horseman. The ride is both thrilling and atmospheric, suitable for older children and adults[6].

  • Trail of Terror (Haunted Corn Maze): An 11-acre maze with spooky elements inspired by local circus folklore and haunted themes. It provides a more intense experience for thrill-seekers[1][6].

  • Family-Friendly Fall Activities: Alongside the thrills, there are fun opportunities for children and families including:

    • Live performances and entertainment scattered throughout the venue
    • Seasonal treats and specialty drinks available at food stations and the Apple Store
    • Scarecrow voting for a community contest
    • Activities like axe throwing and fire art demonstrations with Circle City Fire enhancing the carnival flair[4][5]

  • Apple Store: Celebrates over 40 years with caramel apples and festive snacks unique to the event, providing a sweet complement to the seasonal experience[4].

The festival is handicapped accessible, and admission requires a ticket, with various sales dates depending on membership level. Children under 2 enter free. It is regarded as a beloved fall tradition blending spooky thrills with family fun in the Central Indiana region[1][6].

Schedule and Event Flow (Typical Evening, 5-10 p.m., Thursdays–Sundays):

  • 5:00 pm: Gates open; attendees can explore festival grounds, visit the Apple Store, start food and drink tastings, and enjoy casual entertainment
  • 6:00–9:30 pm: Haunted hayrides depart regularly; visitors can opt for the Trail of Terror maze throughout the evening
  • 7:00–9:30 pm: Live performances and themed activities such as fire art demos and axe throwing sessions occur intermittently
  • 9:45 pm: Last hayride and final activities wind down; guests exit by 10:00 pm when the festival closes[1][4][5]

History and Founding:

The Headless Horseman Festival is a recurring autumn event at Conner Prairie, centered on the folklore surrounding Sleepy Hollow and local ghost stories tied to Indiana’s past, such as circus train accidents. It has grown into a community tradition noted for its immersive storytelling, seasonal ambiance, and inclusive programming for all ages. The Apple Store’s longstanding presence (over 40 years) adds historical continuity and charm to the festival, underscoring its establishment as a Fall heritage event[4][6].