- Scare Dares - It's Halloween at Shining Time Station. Matt and Tanya's cousins Kara and Dan come to visit. Mr. Conductor's cousin takes up residence. Billy Twofeathers is hired as the new engineer. Dan worries that the others won't like him unless he's unafraid, so he tried taking foolish dares to prove himself.
- Oh, What A Tangled Web - Dan and Kara pretend to have jobs and tell Becky that she can have a party in the station. This caused them to run in trouble with J.B. King.
- The Magic is Believing - Amazo the magician comes to visit and he forgot all his tricks. Becky learns about magic when she discovers Mr. Conductor. Billy helped Amazo be more confident, which helped the magician perform his tricks in front of an audience.
- Win, Lose or Draw - The kids enter a drawing contest. Becky does not like her picture, so she asks Mr. Conductor to use his magic and draw her a nicer picture. Schemer steals Billy's ink to draw a self-portrait, but finds out that it is disappearing ink. At the end, Becky learned to appreciate her original drawing and she won third prize.
- Sweet and Sour - Dan, Kara and Becky try their hand at being entrepreneurs when they open a lemonade stand at the station. They make the mistake of trusting Schemer's promise of making a lot of money by making him and his nephew Schemee partners. The business suffers when quality gets sacrificed for quantity as Schemer and Schemee trick their friends into losing their lemonade stand. With help from Stacy and encouragement from Billy and Mr. Conductor, the kids reclaim their business with unexpected aid coming from Midge Smoot!
- Achoo - Mr. Conductor has a cold, but still wants to go to the South Pole and visit his penguin friends.
- A Dog's Life - Schemer found Ginny's lost dog and gave it to the kids.
- Field Day - The kids went to play baseball and Schemer is their coach. Schemer sends Schemee to spy on the opponent's team.
- Wrong Track - Becky was supposed to hold on the money for Stacy's party. Schemer is sad and wants to hear some music, so Becky spends all of the money on the arcade instead.
- Washout - There is a big storm in the Indian Valley. Schemer took out all the signal lights from the store room and put them in the pouring rain. The bridge over the river has been washed out by the storm and the Shining Time staff has to find a way to signal the trains that there is no more bridge.
- Crackpot - Dan collects tickets, Kara collects leaves, Becky collects buttons and Schemer collects combs. Kara is sad when she accidently broke Stacy's tea set.
- Yabba, Yabba, Yabba - Schemee uses walkie talkies to spy on everyone. He also reads Becky's mail and turns the station upside down looking for toys.
- Nickel in a Pickle - Schemer hurts his hand and legs and feels sorry for himself. He even decided to quit his arcade.
- Stop the Press - The kids write a newspaper, but they learn the difference between creative writing and reporting real news stories.
- He Loves Me, He Loves Me Not - It's Valentine's Day at Shining Time Station, and Mr. Conductor is hard at work as Cupid's helper. When Stacy accidentally walks through a cloud of Mr. Conductor's magical love dust, the course of true love goes wildly astray and she falls in love - with Schemer!
- Double Trouble - Mr. Conductor's evil twin causes trouble in the station, and everyone thinks that it is Mr. Conductor's fault.
- Is Anybody There? - Schemer does a radio show in which he is totally unprepared.
- Do I Hear - When Billy and Stacy went away, Schemer organized an auction and sold everything in the station to pay for his broken jukebox.
- Jingle, Jingle, Jingle - The kids and Schemer enter a slogan contest. Schemer thinks that the winning prize is $2,400, so he plans to buy the station and build a parking lot.
- All's Fair - It is the annual fair festival, and Schemer and Stacy enter a pie-making contest.
- Stacy Jones
- Horace Schemer
- Matthew Jones
- Tanya Cupper
- Midge Smoot
- J.B. King
- Mayor Flopdinger
- One Man Band
- Mr. Conductor (Ringo; does not speak)
- Mr. Nicholas (does not speak)
- Harry Cupper (mentioned)
- Schemer's Mother (mentioned)
- Mr. Conductor's Cousin, Mr. Conductor
- Billy Twofeathers
- Daniel "Dan" Jones
- Kara Cupper
- Ginny Johnson
- Barton Winslow
- Felix Perez
- Jake Scoop
- Kevin Knowls "Amazo the Great"
- One Man Band
- Mr. Conductor's Evil Twin
- George Carlin as Mr. Conductor and Mr. Conductor's Evil Twin (20/20)
- Didi Conn as Stacy Jones (20/20)
- Tom Jackson as Billy Twofeathers (20/20)
- Ari Magder as Dan Jones (20/20)
- Erica Luttrell as Kara Cupper (20/20)
- Brian O'Connor as Horace Schemer (20/20)
- Danielle Marcot as Becky (20/20)
- Mart Hulswit as J.B. King (6/20)
- Bobo Lewis as Midge Smoot (5/20)
- Jonathan Shapiro as Schemee (5/20)
- Jerome Dempsey as Mayor Osgood Bob Flopdinger (4/20)
- Barbara Hamilton as Ginny Johnson (4/20)
- Aurelio Padron as Felix Perez (3/20)
- Gerry Parkes as Barton Winslow (2/20)
- Jason Woliner as Matthew Jones (2/20)
- Nicole Leach as Tanya Cupper (2/20)
- Albert Schultz as Jake Scoop (2/20)
- Peter Van Wart as a Passenger (2/20)
- Marium Carvell as Passenger (2/20)
- Cotton Mather as Barton Winslow (stunt double)
- George Thomas as the Elvis repairman
- Peter Wildman as a Passenger
- Washboard Hank as the One Man Band
- Ringo Starr as Mr. Conductor (silent cameo)
- Lloyd Bridges as Mr. Nicolas (silent cameo)
The Jukebox Band
- Craig Marin as Rex
- Olga Marin as DiDi
- Jonathan Freeman as Tito Swing
- Alan Semok as Tex
- Peter Baird as Grace Bass (puppet)
- Kenny Miele as Grace Bass (puppet)
- Vaneese Thomas as Grace Bass (voice; uncredited)
- When George Carlin assumed the role of Mr. Conductor, all Thomas stories from Season 1 were redubbed by him.
- One episode of this season was released on VHS, Sweet and Sour.
- The Thomas the Tank Engine and Friends episodes, "Pop Goes the Diesel" and "Diesel's Devious Deed" were shown out of order in this season rather than the previous season. The third story in the Duck and Diesel trilogy, "A Close Shave for Duck", would not be seen until the following season.
- Two of the episodes in this season feature a first in the series: both episodes feature only one story of Thomas the Tank Engine each. This would later follow in the next season.
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