All Hallow’s Eve, 1862: Two Confederate soldiers, the last of their company, are being hunted in the woods outside Wormwood Ridge. They attempt to defend themselves as the Headless Horseman emerges from the woods and decapitates them.
Halloween, Present Day: Seven teenage friends; Seth, his girlfriend Tiffany, Lizzie, her boyfriend Doc, Nash, Ava, and Liam are driving through eastern Kansas to a party when they stop for gas and directions. Seth finds a “shortcut” through some backroads, but drives over an open bear trap, which destroys the car’s wheel. A young, female tow truck driver named Candy “happens upon” them and takes them to Wormwood Ridge, a town so small it does not appear on the map.
Candy drops their van off at her father, “Pa” Rusk’s garage/junkyard to be repaired and gives the others a tour of the town, which is preparing for the Headless Horseman Celebration, an annual event held every Halloween in Wormwood Ridge since 1806, the year the Horseman began stalking the area for heads according to legend.
The group attempts an escape into the forest on foot but a supernatural mist envelops them and Headless appears on horseback, scattering the group. In the confusion, Tiffany is decapitated and Headless collects her head, then disappears. The others hear church bells nearby and realize they are walking in circles, now back at Wormwood.
In a thrilling conclusion, Liam and Ava lure Headless to the bridge out of town in an effort to destroy him because he cannot cross running water. Candy drives up in the tow truck and using the tow’s cable, Ava and Liam hook Headless then pull him onto the bridge where he simultaneously bursts into flames and melts, causing the bridge to catch fire. Wormwood, the buildings and all the people turn to dust and blow away leaving only Candy, Liam, and Ava alive as the bridge to Wormwood burns.
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