Tucker tells the story, The story begins with a flashback to a battlefield during the American Revolutionary War. Legend says he was a soldier who had his had blown off by a cannon ball.Night after night his ghost would ride through the woods of Sleepy Hollow, searching for a victim to steal it's head to it claim it as his new one.Legend has it that every since then on Halloween night, the ghosts of The Headless Horseman and Ichabod Crane return to sleepy hollow to ride again.Then the story resumes to modern time (when this first aired) at a high school in sleepy hollow. Now a young man politely opens the door for a girl to pass through. He had just recently moved to Sleepy Hollow and was trying hard to make friends and fit in.Gary then tells them that there is now room for two new members. Betty Ann mentions her friend Sam wants to join but needs time to make an initiation story.Gary has someone he wants to sponsor, so he brings in a short person with a burlap sack on his head. The person pulls of the sack of his head and is revealed to be Gary's little brother Tucker and approaches Kiki and tells her "I'll show you small!He then much to her annoyance puts his arm around her.
Then she says that Brad really makes her mad at times.
Then unexpectedly, another young man named Brad (who is Katie's jealous and possessive Ex-Boyfriend) throws a ball at her.
This knocks the decorations out of her hand spilling them on the ground and she snaps at him feeling annoyed.
That evening, Gary seriously and sadly tells the group that friends come and friends go.
Gary is sorry to say that now two members of "The Midnight Society" David and Kristen have left because both of their families have moved away.
Katie really appreciates the help, and she is annoyed when she realizes that Brad accidentally crushed one of the pumpkin decorations. Ian rudely snaps at him and tells him to fix the decoration right away because they're setting up the dance and they both storm off to the school.