As October’s crisp winds sweep through the Midwest, two communities are gearing up to celebrate the haunting legend that has captivated generations: the tale of Sleepy Hollow and its infamous Headless Horseman. This weekend, both Howell, Michigan, and Bradley, Illinois, are rolling out the orange carpet for families, thrill-seekers, and fans of all things spooky, each offering its own unique spin on the classic story.
In Livingston County, Michigan, the much-anticipated Legend of Sleepy Howell is set to transform downtown Howell into a festive playground on October 18, 2025. According to Livingston Daily, the annual event—proudly presented by Howell Recreation—will run from 3 to 5 p.m., promising a safe and vibrant trick-or-treating experience for local children. Organizers describe it as the county’s "largest outdoor trick-or-treating event," a tradition that draws families from both the city and its rural outskirts.
“This longstanding community event offers a fun and safe trick-or-treating experience and helps especially those kids living in rural areas,” Howell Recreation notes, emphasizing the inclusive spirit that has made the event a staple for years.
The heart of the festivities beats along Clinton Street, Court Street, and Church Street, where children in costume can enjoy free trick-or-treating. But that’s just the beginning. The event’s organizers have packed the afternoon with activities designed to delight participants of all ages. The Honk and Haunt Highway (also known as Touch a Truck) will set up shop at the Annex Lot near the Howell Courthouse Amphitheater, giving kids a chance to get up close with fire trucks, police cars, and other big vehicles.
Just around the corner, at State Street and Clinton Street, the Game Zone will be bustling with yard games—think bean bag tosses, giant Jenga, and more. For those with a competitive streak or a penchant for running in costume, the Monster Mile kicks off at 5:30 p.m., followed by the Headless Horseman 5K at 6 p.m. Both races require registration, and they’re expected to draw crowds eager to test their speed against the legend himself.
No Halloween event would be complete without a costume contest, and the Legend of Sleepy Howell delivers. Participants can submit photos of their creative ensembles—worn during the event—by the end of October 19, with winners set to be announced on October 24. The anticipation is already building, as families and friends brainstorm group costumes and clever takes on classic characters.
Across state lines in Bradley, Illinois, the Bourbonnais Township and Kankakee Valley Theatre Association are bringing Washington Irving’s eerie tale to life in a different way. Perry Farm Park, located at 459 N. Kennedy Drive, will be the stage for a re-enactment of The Legend of Sleepy Hollow from October 16 to 18, 2025. According to Shaw Local News Network, this immersive 90-minute experience blends live theater, ghostly encounters, and a spine-tingling wagon ride through the haunted Hollow.
Performances begin at 6 p.m. each evening, with the last entry at 9:30 p.m. on Thursday and at 11 p.m. on Friday and Saturday. Visitors are encouraged to arrive 15 minutes before their scheduled entry time to check in at the Pavilion. With tickets priced at $20 per person and a limited number available each night, organizers are urging interested attendees to secure their spots early—tickets are selling fast, and the event’s popularity only seems to grow each year.
Those lucky enough to attend will witness the mystery surrounding Katrina Van Tassel and her chilling encounter with the Headless Horseman, a figure whose legend continues to haunt the town of Sleepy Hollow. The re-enactment promises to be a feast for the senses, combining atmospheric storytelling, costumed actors, and the thrill of a wagon ride through shadowy woods.
But there’s more to Perry Farm Park’s event than just scares. Admission includes free entry to Harvest Hollow, a family-friendly area packed with games such as Candy Corn Toss, Pumpkin Bowling, and Pin the Head on the Horseman. There’s even checkers for those who prefer a more strategic approach to their autumn fun. Seasonal treats and drinks will be available from Schiel’s Food Service, Candy & Cake, and Bennett-Curtis food trucks, while holiday craft vendors will offer unique souvenirs and gifts.
This year also brings new live entertainment to the festivities. On Friday, October 17, Champagne Experience will take the stage from 6 to 8 p.m., while Saturday, October 18, features Tim the Tuneman during the same time slot. It’s a welcome addition that adds even more energy and variety to an already packed schedule. Event sponsors, including Shoup Manufacturing, First Trust Bank of Illinois, Piggush Engineering, Homestar Insurance Services, Phillips Chevrolet of Bradley, and Riverside Community Credit Union, are helping make the celebration possible.
Both events offer distinct interpretations of the Sleepy Hollow legend, but at their core, they share a commitment to community, creativity, and a little bit of frightful fun. In Howell, the focus is on providing a safe space for children to enjoy Halloween traditions—trick-or-treating, costumes, and games—especially for those who might not have the chance to celebrate in their own neighborhoods. In Bradley, the emphasis is on immersive storytelling, drawing attendees into the world of Ichabod Crane, Katrina Van Tassel, and the Headless Horseman through live performance and interactive experiences.
For families, these events are more than just a night out—they’re a chance to make memories, connect with neighbors, and embrace the magic (and mischief) of the Halloween season. Whether you’re racing through Howell in a superhero cape or clutching your seat on a haunted wagon ride in Bradley, the spirit of Sleepy Hollow is alive and well in the Midwest.
Those interested in Howell’s festivities can find more details and registration information at howellrecreation.org/sleepyhowell, while tickets for the Perry Farm Park re-enactment are available online at btpd.org/tickets or in person at the Perry Farm House & Exploration Station.
As the sun sets and the shadows grow long, both towns are ready to welcome visitors with open arms—and perhaps a little fright. It’s a weekend where the line between legend and reality blurs, and where the Headless Horseman just might make an appearance. Don’t forget your costume, your courage, and your sense of adventure.