Air Date: June 4th, 1989
Thomas Stories: Percy's Ghostly Trick, Woolly Bear
Harry explains to Stacy how a wire and pulley system he set up will automatically take care of the overnight mail. Harry tells Stacy that since all of the work is done for her, she doesn't have to spend the night at the station. Stacy politely tells Harry that she intends on staying overnight anyway.
Matt and Tanya arrive and ask Stacy if she's really going to spend the night at the station. Harry is confident that his mail switching system will work and tries once more to convince Stacy. Stacy again kindly declines, explaining that she's afraid that there might be a malfunction in Harry's system as she wants Shining Time Station to be known as the most reliable station on the line. Reluctantly, Harry then decides to also spend the night with Stacy as he can't leave her by herself.
When Stacy goes off to look for a sleeping bag, Matt and Tanya ponder what spending the night at the station would be like. They are suddenly startled to see a top hat scuttle across the station floor and stop at the arcade stairs. As they go closer to investigate, Mr. Conductor emerges from beneath the hat.
Mr. Conductor explains that he found the top hat in the lounge car on the express to Twiddly Junction. He comments that they look as if they’ve just seen a ghost. The kids claim that they knew all along that it was Mr. Conductor, but he catches on and teases the kids for being frightened. He tells them that he would've been just as frightened to see such a sight and would have jumped and screamed.
Since Stacy and Harry intend on staying overnight, Matt and Tanya decide they want to as well, and beg Stacy to let them do so. Stacy makes it conditional on if their parents give their permission. The kids become excited and Stacy remarks that their parents haven't even agreed yet.
Just then, a woman wearing an ornate paper hat and costume calls out to Stacy. It's Wendy Brackman, an old friend of Stacy's. She introduces Wendy to the Matt and Tanya who are curious and ask her about her appearance. Stacy reveals that Wendy can make anything out of paper, and Wendy adds that she makes hats but likes making masks. Stacy asks Wendy if she could show demonstrate her talents to the kids as she goes to the ticket desk to call the kids' parents. The kids want to make scary masks and when we next see them, Tanya is wearing a dragon-like mask as Wendy makes a skeletal one for Matt. Wendy bids everyone goodbye just as her train arrives. Stacy breaks the good news to Matt and Tanya that their parents agreed to let them spend the night at the station.
Schemer tries to frighten them by telling them about how scary the station is at night in the dark with the boogieman, and tells them about "the man with his head on backwards", who used to frighten Schemer when he was small. They run off outside to play as Schemer complains that today's kids aren't as afraid as he was at that age. Schemer suddenly experiences a “Genius Time” moment, and decides that the kids need something to be afraid of.
That night, Tanya and Matt are in their sleeping bags. Harry joins them from his workshop with a blanket roll. When the kids tell him that they can't sleep, Harry shares his experience of being the same way when he drove the overnight train to Pelican Falls. Harry then leaves the kids and goes into his workshop.
The kids try to sleep but a screeching sound startles them. Schemer discreetly places a nickel in the jukebox. Tito awakens his band mates to tell them that a mysterious hand just gave them a nickel to play something. The band sleepily begins to play a slow version of “Clementine”.
The kids are still pondering who played the jukebox when Stacy comes in to check in on them. She's surprised to find them still awake and tucks them in pretending that she's putting them into envelopes (their sleeping bags). She tells them that she'll be in Harry's office and that she'll see them in the morning.
The kids become increasingly startled when they hear crashing sounds. Stacy and Harry rush out of the workshop having heard it too. Harry and Stacy decide to investigate, reassuring the kids that it was probably the wind knocking something over.
Just then, a figure covered in a white sheet and wearing a ball cap slinks into the station, but retreats when Harry's voice is heard. Stacy notes that the Midnight Special is due any time with the night mail, and Harry is eager to see if his pulley system works. As they both leave the station, the sheeted figure returns, but is revealed to be Schemer when he steps on the sheet and pulls it off. Irritated at being foiled, he throws the sheet away and it lands over the wire of Harry's pulley system. In another "Genius Time" moment, Schemer decides to become "the man with his head on backwards" to frighten the kids.
The kids complain that their sleeping bags are knotted at the bottom, so they both dive inside their bags to fix them. Schemer has put his jacket and cap on backwards and walks towards the kids. He becomes frightened himself when he glances around and sees two sleeping bags standing upright and wriggling. Schemer runs off screaming and knocks himself out when he bumps into the jukebox, waking up the puppets. As he runs toward the station's exit, the kids' paper masks are lit up from behind by the passing Midnight Special, while the sheet is caught by the mail bag sliding across the pulley system and pulled ghostlike across to the other side. Convinced he's just seen the real man with his head on backwards, an unnerved Schemer panics and runs away screaming just as Harry and Stacy come back into the station.
The kids complain of being tired, while Harry congratulates himself that his system worked and the mail is now ready to be picked up by the Daybreak Express. Stacy concurs but says that she wanted to be there to be sure. Harry and Stacy lay out their bedding beside Matt and Tanya as the kids chide them to get to sleep. Everyone wishes one another goodnight, even in the jukebox. The episode ends with Schemer, coming out of hiding saying a very quick "good night" frightening Stacy, Harry and the kids, who then laugh it off.
Tropes featured in this episode:
- Bedsheet Ghost: Schemer tries to be one in his first attempt to scare the kids.
- Brick Joke: Mr. Conductor states he has to take his pajamas out of the dryer. He appears later actually wearing them.
- Jump Scare: Schemer gives one at the end of the episode. This is Played for Laughs.
- Running Gag: When the kids keep telling everyone they're not sleepy, the adults keep saying "just close your eyes and pretend you are". Lampshaded by Matt.Matt: Why do grownups always say that?
- Slumber Party
- Tempting Fate: Subverted. Matt and Tanya talk about how it isn't going to be scary to sleep at the station. Then a top hat comes in floating on the ground. It turns out to actually be Mr. Conductor, though.
- You Look Like You've Seen a Ghost: Mr. Conductor states this after he gets out from under the top hat he found.
