Headless Horseman

Headless Horseman

Year: 2007

Runtime: 87 mins

Language: English

Director: Anthony C. Ferrante

Horror

Seven college students take a shortcut to a party and end up in the abandoned town of Wormwood. Bones and odd ornaments line the streets, recalling a legend: a mad man beheaded local youths on All Hallows’ Eve a century ago, and the townsfolk decapitated him in revenge. Every seven years his spirit returns, demanding seven heads, and the visitors are hunted one by one.

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Timeline – Headless Horseman (2007)

Trace every key event in Headless Horseman (2007) with our detailed, chronological timeline. Perfect for unpacking nonlinear stories, spotting hidden connections, and understanding how each scene builds toward the film’s climax. Whether you're revisiting or decoding for the first time, this timeline gives you the full picture.

1

Origin of the Headless Horseman

In All Hallows' Eve of 1862, the Headless Horseman emerges from the woods outside Wormwood Ridge and decapitates two Confederate soldiers. The brutal act seeds a long-standing fear in the town, and Montgomery’s body is later hanged in the square. His spirit is said to return on Halloween to collect heads.

1862 Woods outside Wormwood Ridge
2

Halloween preparations and legend

Present-day Wormwood Ridge is bustling with a yearly Headless Horseman Celebration dating back to 1806. Candy explains Calvin Montgomery’s murderous past and that his spirit supposedly rises every seven years to claim seven youths’ heads. The legend casts a shadow over the town’s Halloween festivities.

Present day Wormwood Ridge
3

Shortcut and car trouble

Seth and his friends take a backroad shortcut that ends with a broken wheel after driving over an open bear trap. Candy stops to help and leads them to a junkyard near her father Pa Rusk’s place. The stage is set for danger as the car situation grows worse.

Present day Eastern Kansas / Wormwood Ridge outskirts
4

Van left at the junkyard

Candy drops the group off at Pa Rusk’s garage and gives them a tour of Wormwood Ridge’s odd history. The van goes missing, prompting Seth to search the junkyard and encounter a looming threat. The mood turns ominous as the town’s secrets begin to reveal themselves.

Present day Pa Rusk’s garage / Junkyard
5

Seth is decapitated

While searching the junkyard, Seth is confronted by a headless figure and decapitated. Headless then takes his severed head and disappears into the yard. The remaining friends realize the danger is immediate and deadly.

Present day Pa Rusk’s junkyard
6

Ava finds the body and warns the group

Ava discovers Seth’s lifeless body and immediately informs the group about the threat they face. Candy recounts Montgomery’s legend, stressing that Headless will keep hunting for seven heads unless they can stop him. The survivors begin to grasp the stakes of their predicament.

Present day Pa Rusk’s junkyard
7

The seven-heads curse explained

Candy explains that Montgomery’s spirit rises to collect seven youths’ heads every Halloween and that Wormwood’s existence hinges on preventing this fate. The idea of a recurring, supernatural hunt galvanizes the group to avoid capture. They realize escape is their only option.

Present day Wormwood Ridge
8

Forest escape and Tiffany’s death

The group tries to flee into the forest, but a supernatural mist envelopes them and Headless appears on horseback. Tiffany is decapitated, and the others find themselves back in Wormwood, realizing they are trapped in a deadly loop. They split up to search for weapons and a possible vehicle.

Present day Forest near Wormwood Ridge / Wormwood Ridge
9

Gun theft and Doc’s death

Lizzie, Liam, Nash, Doc, and Ava split up to find a working car and weapons. The trio steals several guns from Kolchak Stillwall's general store, trying to level the odds. Headless then appears and decapitates Doc during a tense confrontation.

Present day Kolchak Stillwall's General Store
10

Pa Rusk captures the trio

Pa Rusk returns to town and confronts Liam, Ava, and Lizzie, dragging them back into Wormwood at gunpoint to hand them to Headless. The trio is forced toward a grim fate as the town’s dark secrets tighten their grip.

Present day Wormwood Ridge
11

Candy frees them and stakes explained

While Pa Rusk is away, Candy frees the remaining trio and reveals that Headless will wipe Wormwood from existence if seven heads aren’t gathered. She also reveals her own plan to escape with the others and survive the night.

Present day Wormwood Ridge
12

Lizzie’s death and the officer’s fate

911 is called, but the officer is killed by Wormwood’s inhabitants as Headless decapitates Lizzie. The group realizes the town has become a trap with no easy exit.

Present day Wormwood Ridge
13

Candy and the final assault on Pa Rusk

Candy steals Pa Rusk’s tow truck and uses it to confront Headless’s minions as the trio makes for the bridge. She intends to turn the vehicle into a weapon to secure an escape.

Present day Wormwood Ridge
14

The bridge trap and Headless melts

Liam and Ava lure Headless to the bridge outside Wormwood, where he cannot cross running water. Candy attaches the tow cable and, with Liam and Ava, pulls Headless onto the bridge; the figure bursts into flames and melts as the bridge catches fire. Wormwood, the buildings, and the people turn to dust, leaving only Candy, Liam, and Ava alive.

Present day Bridge over the river near Wormwood Ridge
15

Aftermath

The bridge burns away and Wormwood vanishes, leaving a stark dawn for the surviving trio. They walk away, shaken by what they endured and the cost of breaking the Night's curse. The legend ends for now, with three survivors carrying the memory of Wormwood Ridge.

Present day Bridge area / Wormwood Ridge outskirts

Last Updated: October 09, 2025 at 15:10

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Headless Horseman Summary

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