Halloween Video: The Headless Horseman

The Headless Horseman rides again at Keeneland.

Every Halloween season, fans at Keeneland are treated to one of the most iconic sights in horse racing — the Headless Horseman galloping down the track in eerie, dramatic fashion.

Draped in a flowing black cape and carrying his signature jack-o’-lantern head, the horseman thunders past the grandstand each year to the cheers (and delighted shrieks) of racegoers. It’s a hauntingly perfect nod to Keeneland’s deep Kentucky roots — and a reminder that horsemen (and horsewomen) have always known how to make an entrance.

The tradition has become a favorite moment for both fans and staff, adding a touch of spooky magic to fall racing season. Whether you’re there for the speed, the spectacle, or just the pumpkin-headed theatrics, the Headless Horseman never disappoints.

Watch below as the legend rides once more through the Bluegrass mist:

Happy Halloween, Horse Nation. Go riding!