The cover illustration depicts a headless figure in a field with many pumpkins holding a green head in his left hand and placing his right hand on a pumpkin that has a face carved into it. There is a full moon in the background.
Brandon Plush is a cruel bully who loves to scare people, especially his sister Maya and cousin Vinnie. He babysits two kids named Jennifer and Ray Sullivan and uses his visits to scare them with stories, such as one about a headless boy living in their basement. After he pretends to be the headless boy, Mrs. Sullivan calls Brandom's Mom, who doesn't approve of his scaring. The next day, he plays a prank on Vinnie where he pretends to spill acid on him, which is seen by the science teacher Mr. Benson, who Brandon hates due to his strictness.
He punishes him by making him clean the science lab, and Brandon starts planning his revenge. He and his friend Cal plan to break into Mr. Benson's house on Halloween night, but their plans are halted when Mrs. Plush forces Brandon to take Maya, Vinnie and their friends trick or treating. But they are quickly able to ditch them. They leave Vinnie at the steps of a supposedly haunted house and soon hear a scream, but Brandon tells Cal to just ignore it.
After scaring some trick or treaters, they sneak into Mr. Benson's house to trash it. However, two scary dogs he has chained up break out and chase the kids. Brandon sees Raven's Ravine, an infamously steep ravine that no one has ever been able to jump across. He tries to jump across it and seems to make it to the other side, but he doesn't recognize any of the streets on the other side.
Brandom bumps into a kid with the same monster mask he has, who introduces himself as Norband and invites him to a Halloween party. The party seems normal until Brandon is forced to eat a worm-filled doughnut and bob for cockroaches. He manages to get out of the house but is stopped by some zombie hands and head popping out of the grass. He escapes them and ends up back at Raven's Ravine, and thinks he sees Cal’s dead body at the bottom, but after taking a closer look he realizes that what he is looking at is his body
Norband appears and explains that Brandon died while trying to jump the ravine, and he's now in the spirit world. Brandon asks if they can give him another chance, and Norb says he will get another chance at life if he can save three scared people in one hour. Brandon is given his body back for the hour and goes to save people. First, he sees Cal still being threatened by Mr. Benson's angry dogs.
Cal is able to escape while the dogs are paying attention to Brandon, who distracts them with candy. He comes across the house he abandoned Vinnie in and goes in, but Vinnie warns him to leave, as there is a horrible ghost keeping him there. An ugly ghost then appears and Brandon attempts to scare him off with his headless disguise, which works. However, Vinnie reveals that it wasn't the ghost. It was the ghost's pet, and that the whole house is evil.
The house comes to life and starts making Vinnie spin in a chair. Brandon figures that the ghost might be stopped by light, so he shines a flashlight on the walls. This works and they retreat, giving the two time to escape. Vinnie goes back to his house, leaving Brandon with only one more person left to save. He sees Maya being threatened by three bullies and tries to use his headless routine. It fails and he is forced to climb a tree. Suddenly, Brandon's hour runs out and his spirit falls out of body, scaring the bullies away.
He goes back to Norband, who takes off his mask to reveal Brandon's face, which he pulls off to reveal no head. He went as Brandon for Halloween, and this was all a joke he and his friends played on him. They never planned on giving back his body. However, Brandon realizes it's still Halloween, and suggests they go out and do some serious scaring.
- The French tagline is "Même pas peur !", which can be translated to "Not even afraid!"
- In the UK, the excerpt on the back was changed. The sentence 'Hair caked with dirt.' was changed to 'Hair caked with earth.' .
- Cal mentions seeing beer in Mr. Benson's fridge. This is one of the only times an alcoholic drink comes up in any Goosebumps book.
- In this story, there is a cousin named Vinnie. There is also a cousin named Vinny in Slappy Birthday to You.
- This could also be a slight reference to the film My Cousin Vinny.
- Stine reportedly finished writing this book on January 28, 1998.
- The book would later have similarities to the story The Halloween Dance, released as part of R.L. Stine's 2001 anthology, The Haunting Hour three years after Headless Halloween's original release. In the story, the main character seemingly survives something on Halloween night, only to turn out to have died. He also invited to a scary party by a ghost. The rest of the story then involves the main character's journey towards what appears to be a way for them to undo their death.
- This is one of few Goosebumps books written from the perspective of a bully character.
- It's also one of the few Goosebumps books where the protagonist dies during the story.
- This book's plot of a character needing to perform three good deeds to be saved would be used again in Slappy's Nightmare.
- This book references Jell-O, Air Jordans, Darth Vader, The Little Mermaid, Princess Leia, Snickers, M&Ms, and Twister.
|Goosebumps Series 2000 series|
|#01 Cry of the Cat||#10 Headless Halloween||#18 Horrors of the Black Ring|
|#02 Bride of the Living Dummy||#11 Attack of the Graveyard Ghouls||#19 Return to Ghost Camp|
|#03 Creature Teacher||#12 Brain Juice||#20 Be Afraid — Be Very Afraid!|
|#04 Invasion of the Body Squeezers: Part 1||#13 Return to HorrorLand||#21 The Haunted Car|
|#05 Invasion of the Body Squeezers: Part 2||#14 Jekyll and Heidi||#22 Full Moon Fever|
|#06 I Am Your Evil Twin||#15 Scream School||#23 Slappy's Nightmare|
|#07 Revenge R Us||#16 The Mummy Walks||#24 Earth Geeks Must Go!|
|#08 Fright Camp||#17 The Werewolf in the Living Room||#25 Ghost in the Mirror|
|#09 Are You Terrified Yet?|