Headless Horseman Festival at Conner Prairie

Updated 9/24/2024

Deep-rooted in over 1,000 acres of history, Conner Prairie is renowned for its thrilling fall event, the Headless Horseman Festival. This festival offers an array of events and activities, and its immense popularity in central Indiana draws an average of 2,500 attendees nightly.

The Headless Horseman has appeared at Conner Prairie for more than four decades. It is a Sleepy Hollow essential to your family’s Fall bucket list!

Festival Activities

The world of Sleepy Hollow at the Headless Horseman Festival is a mix of mystery, thrills, and fall family fun—all wrapped up in seasonal treats, spooky vibes, and live entertainment.

The Conner Prairie grounds are packed with activities that make it feel like you’ve wandered into an autumn storybook. Think carnival-style thrills, delicious eats, specialty drinks, and entertainment for both kids and adults. You can test your aim at axe throwing, watch fire turn into art with Circle City Fire, or catch live music and magic shows under the crisp October sky.

For the littles, there’s the Barrel Train Ride through a musical pumpkin patch (for riders under 48″), while bigger kids and the brave-at-heart can conquer the Perilous Plunge dry tubing hill, get lost in corn mazes, or face the newly reimagined Trail of Terror. Add in eerie illusions, Sleepy Hollow-themed shows (from marionettes to a one-man act), and nonstop performances, and you’ve got an October tradition.

Headless Horseman

Featuring both rides during the day and evening, the Headless Horseman offers both a scary and festive element to Fall. The Haunted Hayride brings the Headless Horseman alive through a seated hayride through Conner Prairie, where the Headless Horseman himself shows up.

Based on the classic tale, the Headless Horseman comes alongside the tractor wagon, riding a horse with a sword. While this may seem frightening to young children, it wasn’t as scary as I anticipated, and I did see many families with young children on the night ride. The night rides may be scarier to young children than daylight rides.

We took one of the last tractor rides available in the evening. Plan to wait for the Haunted Hayride; we arrived on a jam-packed night at 7:30 p.m. and received tickets for the 10:15 p.m. ride (then waited an additional 45 minutes in the line after 10:15). If you are taking little ones, prepare for this in advance!

If you arrive before 10 p.m., characters will sing traditional songs while waiting in line. For the evening ride, expect a few scares, such as spooky music, displays, and possibly some jump scares in addition to the Headless Horseman.

Corn Mazes

The Conner Prairie corn maze has been voted among the top 10 best in the country! How cool is that!? {and that’s just one awesome fact!}

Long Maze: Test your wits in our family-friendly long maze, which can take up to one hour to complete.
Short Maze: Bring the little ones to our shorter kids’ maze, which takes 30 minutes to complete.
Trail of Terror Maze: Brave the spooky Trail of Terror after dark—recommended for ages 10+. Guests will experience sounds, effects, lights, and live scare actors. The attraction is open from sunset to 10 p.m.

Important Maze Info

Admission is included in your Festival ticket.
The short and long mazes are open during Conner Prairie’s open hours and the festival. The Haunted Trail of Terror is only open during the evenings of the Headless Horseman festival.
The short maze is suitable for children, while the long maze is suitable for teens and adults. Guests ages 15 and younger must be accompanied by an adult.
Corn maze paths are 5 feet wide.
Wheelchairs and strollers are not advised.
Using the restrooms BEFORE the maze is recommended.

Sleepy Hollow Tavern

The festival will offer a variety of food options throughout the grounds, including burgers, pizza, pretzels, kettle corn, and more. Stop by the Sleepy Hollow Tavern for your favorite beverages like Conner Scary and Sun King’s exclusive Headless Horseman beer.

Tips for Visiting:

Headless Horseman is a rain-or-shine festival!
Tickets can be purchased online here. If tickets are not “sold out in advance,” they will only be available at the gate.
Plan to spend 2-3 hours at the festival (longer on busy nights & weekends).
Please arrive 45 minutes prior to your selected hayride time to allow ample time for check-in and walking to the hayride.
Children are always encouraged to come dressed up in Halloween costumes. Please refrain from wearing masks.
Photos are allowed during the tractor ride, but flash photography, tripods, and other equipment are not.
Children aged 15 and under need to be accompanied by an adult.
Bring extra money if you want to purchase beverages and food or ride the 1859 Balloon Voyager.
Food will be available for purchase, including hamburgers, hot dogs, chicken strips, French fries, hot pretzels, cotton candy, elephant ears, kettle corn, and various hot and cold beverages.

Stay in Hamilton County

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