A horse-drawn wagon carrying children travels down a road under a large full moon on a spooky Halloween night, with bats flying in the sky and jack-o'-lanterns on the ground.
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Sleepy Hollow Haunted Wagon Rides

Haunted horse-drawn wagon ride through Sleepy Hollow.

About

Experience the thrill of Sleepy Hollow Haunted Wagon Rides, a unique Halloween tradition in Billings. Journey through a spooky landscape on a traditional horse-drawn wagon, pulled by powerful draft horses. Listen to an animated narration of the Legend of Sleepy Hollow, encountering eerie scenes and props along the way. While designed to be spooky, the event is appropriate for all ages, though it becomes naturally scarier in the darkness of later evening. This is a must-do fall activity for families seeking a memorable Halloween adventure.

Our Take

Scare Factor

👻 👻 👻 (3/5)

Family Friendly

👶 👶 👶 👶 (4/5)

Best For

Families and thrill-seekers

Vibe

Spooky and adventurous

Energy Level

Moderate

Budget

$$

Photo Friendly

Limited (no flash photography)

Weather Sensitivity

Moderate (dress appropriately)

Tags

haunted wagon ridefamily friendlyhalloween festivalfall festivalghost tourcommunity eventbillingshaunted attraction

Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.

Location

3740 Wise Lane
Billings, MT

Event Details

Pricing

$20

Duration

Approximately 1-2 hours per ride

Ages

All ages (2 and under free)

Timed Entry

Yes

Organizer

Sleepy Hollow Montana

Practical Information

Pet Policy

No pets allowed

Food & Drink

Hot chocolate, hot cider, and other goodies available for purchase.

Quick Actions

Tips & Advice

  • Book tickets in advance, as seating is limited and most nights are expected to sell out.
  • Dress in layers and bring a blanket for warmth, as the wagon ride can be cool, especially in the evening.
  • Avoid using flash photography during the ride, as it can detract from the spooky atmosphere.
  • Double-check your GPS directions to ensure you are heading to Oscar's Park via the South Frontage Road or Shiloh Overpass, not South Billings Boulevard.
  • Consider visiting earlier in the evening if attending with very young children, as the experience naturally becomes scarier after dark.

Frequently Asked Questions

Is the wagon ride too scary for children?

The event is suitable for all ages, with a Halloween theme that is eerie but not overly frightening. It includes spooky scenes and props, and the Headless Horseman may make an appearance.

What is the cost of admission?

Tickets are $20 per person. Children aged 2 and under are free and will sit on a lap.

Where is Sleepy Hollow Haunted Wagon Rides located?

They are located at Oscar's Park, 3740 Wise Lane, Billings, Montana, near the Yellowstone River.

What should visitors bring?

Visitors are recommended to dress appropriately for the weather and are welcome to bring a blanket. Flash photography is not permitted.

Are concessions available?

Yes, hot chocolate, hot cider, and other goodies are available for purchase.

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Contributors & Updates

Last Updated: Nov 11, 2025
Original Submitter: Sep 17, 2025 The Halloween Events Near Me editorial team

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