Headless Horseman Conner Prairie Festival: 10 Activities to Fright & Delight

Headless Horseman Conner Prairie Festival: 10 Activities to Fright & Delight

Nothing says fall to me quite like the Headless Horseman Festival at Conner Prairie. This festival is a classic for a reason so make sure you get your tickets to enjoy everything it has to offer. Conner Prairie’s grounds are always beautiful, but they look truly fantastic during the festival. This Instagram-worthy event includes midway games, Halloween-themed shows, fortune-telling, barrel train rides, haunted hayrides, corn pits, a giant corn maze, food trucks, and more.

So many of my friends haven’t visited the Headless Horseman Conner Prairie Festival because they think it’s just a spooky hayride, but it’s so much more! You’ll easily fill an entire evening or two with all of the fun activities offered.

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Headless Horseman

Conner Prairie Festival: 10 Activities to Fright & Delight


1. Headless Horseman Hayride

Take the iconic haunted hayride through Conner Prairie’s grounds where you will encounter spooky frights around every corner…including the Headless Horseman himself! The Headless Horseman hayride is the main event of this awesome festival and for good reason. Be mindful of your timed ticket for this event as you will need it to get on the hayride.

When it’s almost time for your hayride to start, make your way towards the Featherstone Barn to queue up for your spot. When it’s your group’s turn to enter the hayride area, you will slowly move through the line past what is normally the Lenape Indian Camp. During the festival, the camp is turned into the town of Sleepy Hollow. While waiting in line, you will pass lots of volunteers who are dressed in period costumes looking and acting creepy!

The hayride is awesome. We rode at around 10 pm so it was a little spookier than a daytime ride. My nearly 5-year-old loves all things spooky so she was totally into all the jump scares. Be warned though, there were a few frights that had some teenagers in our wagon jumping. It was so cool to ride the wagon through the dark forest on the grounds. Conner Prairie seriously goes all out for this festival. Everywhere you looked along the route were spooky decorations and scenes. The Headless Horseman rides a real horse (really close!) to the wagon which makes this hayride extra spooky/fun.

For a less spooky ride, opt for an earlier ticket. The daytime rides are much more about fun for the little ones. In full daylight it is less scary, but the actors are also not trying to scare little kids. If you are on a later ride, sit closest to the front or in the middle if there are interior seats in your wagon.

2. Trail of Terror Corn Maze

Enjoy the Trail of Terror, the spooky path through Conner Prairie’s gigantic cornfield filled with elevated frights for those who dare to be scared! Did you know this maze is rated among the Top Ten Corn Mazes in the U.S.? This seriously cool maze is spread out across 12 acres and is full of fun for the whole family. There is a shorter maze for younger kids as well as a longer maze for teens and adults. During the Headless Horseman Festival, there is even a Spooky Maze for kids 12 and older. Take a map and practice your patience as you wind your way through this maze.

Make sure you save time during your visit to try your hand at completing the maze. My kids love to adventure through and explore this amazing maze later in the evening when it’s dark but the maze is lit up from above. From a kid’s perspective, this maze must feel enormous. The Corn Maze is included in the price of admission to the festival.

3. Magnificent Midway Carnival

Experience the Magnificent Midway with the Spinning Apples carnival ride, festive games including Cauldron Toss, Zombie Soccer, and Monster Mini-Golf, a karaoke tent, corn pits, and bounce houses for the littles. The midway games are such a hit among the younger crowd and a great way to spend time while waiting for your hayride.

4. Barrel Train Ride

The barrel train rides are SO FUN. This ride is suitable for kids ages 9 and under. Each seat has a seatbelt so this ride can be enjoyed by young children too. A tractor takes the kids on a (moderately) slow ride through a roped-off area. The train rides are included with the price of admission so make sure you set aside time for a few rides. My daughter rode the train at least 5 times and loved it each time.

5. Sleepy Hollow Marionette Show

The Headless Horseman Festival has amazing family-friendly shows each night. The shows run on set times each night and are located inside tents just off the midway. This year, check out the Sleepy Hollow Marionette Show! The shows are especially great for those who want to take a seat and rest after a fun evening of running around.

6. ‘Mis’-Fortune Telling

Have your mis-fortune told by Carl Voyant at the Fortune-telling booth! My kids love making a quick stop here on their way to the hayride. You never know what Carl is going to say!

7. Tubes of Terror

Take a thrilling ride down the thrilling Tubes of Terror Dry Tubing Hill. You’ll need to lug a tube from the bottom of the hill to the top so get in line and get ready to work!

8. Live Music

There is a live DJ spinning Halloween music all night mixed in with live music performances from Sweet Tunes.

9. Live Shows

Check out the Sleepy Hollow One-man Show and Eerie-llusions Magic Show. Last year, we watched the magic show and my daughter loved it. The magician was truly funny and very good with illusions. There was a fair bit of audience participation as well. We peeked in during the Professor Steve cooking show as well and saw lots of very happy and amused families.

10. The Bizarre Bazaar

The Bizarre Bazaar is a whimsical mini-‘museum’ dedicated to the legend of the Headless Horseman. Learn all about the history of the mysterious lone rider.

Food at Conner Prairie

There is so much tasty food to eat at the festival. The Prairie Grill has drinks and hamburgers, hot dogs, fries, hot pretzels, etc. The delicious Apple Store will be open from 6:00 pm – 9:00 pm. Food trucks are available along with carnival-type food such as funnel cakes, lemon shake-ups, and ice cream. Sprinkled throughout the midway were a few tents selling soft pretzels, roasted nuts, kettle corn, and more. Did I mention there is beer? Make sure to try the Sun King Brewery’s Ichabrewed Crane beer and take a step inside the Witches Den to try a bubbly concoction.

Tickets for the Headless Horseman Conner Prairie Festival

The Headless Horseman Festival runs Thursdays – Sundays October 5 through 29, 2023. Hours are 6:00 pm – 10:00 pm. Festival tickets go on sale to the public on September 7. Tickets will also be available to participants enrolled in the Access Pass program. Tickets must be purchased for anyone 2 years or older.

Festival admission does not include hayride tickets. Timed hayride tickets are separately ticketed. Guest festival admission is $24 or $31 with a hayride ticket. Members receive free festival admission. Member admission + hayride tickets are $7.

Parking at Conner Prairie

Parking is free and located in the grassy area beside the main parking lot. Conner Prairie has the parking lot game on lock. There are dozens of volunteers stationed throughout the parking lot to flag people into the right spot. Be prepared for inclement weather as you will be parking on the grass.

Tips for a Successful Night

  • Gates are open from 6:00 pm – 9:30 pm. Purchase your tickets in advance and reserve the hayride time of your choice.
  • Headless Horseman is popular so be prepared for lines at the gate. I always think my kids do better when they know they will have to wait ahead of time.
  • Activities and hayrides run until 10:00 p.m. or later.
  • You will reserve your Headless Horseman hayride tickets in advance when you buy your tickets. Plan on arriving 45 minutes before your hayride time.
  • Tip: Grab early tickets for younger kids so it’s not dark or as spooky, instead it’s just a little startling and fun.

Good To Know

  • Kids 15 and younger must be accompanied by an adult at all times.
  • The festival is spread out on the grassy areas of Conner Prairie so dress accordingly.
  • The 1859 Balloon Voyage will be offered until 10:00 p.m., weather permitting. Tickets for the balloon ride are an additional cost of $18 for non-members and $14 for members. Youth balloon tickets are $10 for non-members and $9 for members. Consider checking out the balloon during your visit to Conner Prairie as the fall leaves and corn maze will make for a breathtaking view.
  • The hayride is ADA accessible, however, you may want to discuss any questions or concerns with Conner Prairie Guest Services in advance by calling (317) 776-6000.

The Headless Horseman Festival at Conner Prairie is an Indiana tradition for a reason. It’s one of the best fall festivals in town. Make sure you get your tickets early so you don’t miss out on this amazing experience.


3 thoughts on “Headless Horseman Conner Prairie Festival: 10 Activities to Fright & Delight”

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