The Headless Horseman Rides in to Conner Prairie

Fall arrived with a vengeance this week - perfect for ushering in the annual Headless Horseman fun at Conner Prairie! Of all the Fall family to-dos in the Indianapolis area, this one is in our family's top 5. And if you're planning a visit this season, let's prep you with the rundown of what to expect...

Headless Horseman Conner Prairie - theCityMoms

Headless Horseman Festival Activities at Conner Prairie:

Tons of games and activities in the midway

This is where the magic of the festival starts: It’s the perfect place to try your hand at festive games like Cauldron Toss, Zombie Soccer and Monster Mini-Golf, hop on a carnival ride, or check out the Scarecrow Patch. The midway activities when you enter the gates at the outdoor Headless Horseman experience have tons of stuff to entertain all ages. I’m excited about the Circle City Fire show coming in 2025.

Headless Horseman Conner Prairie - theCityMoms
Headless Horseman Conner Prairie - theCityMoms

Photo credit: Conner Prairie


Shows, performances, and more shows

Mini acts pop up all over Headless Horseman, from the fan-favorite Stevens Puppets marionette show of The Legend of Sleepy Hollow in the big red barn (perfect for warming up) to Ty Stover’s one-man take on the tale down in the Symphony on the Prairie bowl. I like to make time for a warm cider while catching the ongoing broadcast of the classic cartoon version we all grew up with too.

Headless Horseman Conner Prairie - theCityMoms

That Conner Prairie Corn Maze

Conner Prairie keeps upping the ante on their 12-acre corn maze. Details:

  • The maze offers two routes: a shorter option designed for younger kids and a longer, more challenging path for teens and adults. Children 15 and under must be accompanied by an adult.

  • In 2025, watch for an updated Trail of Terror Scary Maze!

  • The maze is included in your Headless Horseman admission.

  • Get lost? There are checkpoints along the way to help navigate + guide you. In worst case scenarios, there’s also a helpline to call.


Food galore

In addition to all the usual Conner Prairie food stand options, the Apple Store - powered by the amazing Conner Prairie Women's Alliance - is a must-stop for caramel apples, hot cider to warm our bones and plenty o' treats.

Best news? The Apple Store is open for any drop-in visitors, Wednesdays-Sundays from noon-5pm OR during Headless Horseman hours until 9pm. No tickets required to pop in here!

Headless Horseman Conner Prairie - theCityMoms
Headless Horseman Conner Prairie - theCityMoms

The Haunted Hayride

Confession: We’ve lived in Indy for over 10 years, gone to Headless Horseman almost every season, and somehow never done the Haunted Hayride. (Why? My husband’s horribly allergic to hay!) With him coaching soccer one evening last year, my daughter and I finally jumped in line.

Headless Horseman Conner Prairie - theCityMoms
Headless Horseman Conner Prairie - theCityMoms
Headless Horseman Conner Prairie - theCityMoms
Admittedly, this photo is a few years old but to my delight I heard a friendly voice while we were standing in line this year, turned, and it was this same volunteer who has helped us at Headless for the past 4. Hello friend!

This pic is a throwback, but fun fact — the same sweet volunteer has helped us at Headless for 4 years running. Hello, friend!

Headless Horseman Conner Prairie - theCityMoms

Tickets are sold in half-hour increments, and thanks to front-of-the-line passes we were on quickly. The wait winds through Conner Prairie’s Lenape Village - dimly lit, a little spooky, perfect for setting the mood. I’ll admit, I was nervous since my daughter scares easily, but the “scarers” were obvious enough that it felt fun, not terrifying. The ride runs about 15 minutes, and yes, you do get a few brushes with the Headless Horseman himself.


The Tubing Hill

The Perilous Plunge dry tubing hill is now such a family favorite - the kids love the thrill of zipping down a slide without the snow. And the littlest adventurers in our group never seemed to tire out rom racing back to the top for another ride. I’d say to expect this to be one of the most popular stops during your Headless Horseman visit.

Every year Conner Prairie ups the ante with Headless Horseman, and this experience secured its spot in our family’s Top 5 Fall Fun. Do I see that changing anytime soon? Absolutely not. You can bet your head on it.


MORE INFO: Conner Prairie is at 13400 Allisonville Road in Fishers. Headless Horseman runs 6–10 pm, Thursdays–Sundays, October 2–26 (some activities/hayrides may run later). Tickets are available at connerprairie.org or on-site if not sold out. Admission is $26 per person; members are free. Hayrides are $10 per person for both members and nonmembers. Details may change, so check the Conner Prairie website before visiting.

Special thanks to CityMom Abby for allowing us to feature her kiddos in this post as well! 

Jeanine Bobenmoyer

Jeanine is a mom of teens, yoga-addict, Michigan native, and avid reader. Her dream vacation includes her family and national parks. Jeanine is a veteran of the advertising industry and a former editor.

As theCityMoms’ Chief Executive Officer, she oversees our brand strategy and business operations, and regularly represents theCityMoms via TV, livestream, and other appearances with our media partners. Connect with Jeanine on Instagram and LinkedIn

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