January 29, 1989–
- A Place Unlike Any Other - In the first episode, we are introduced to the main characters and inhabitants of Shining Time Station. Stacy Jones, the new station manager, arrives at Shining Time Station and shows her nephew, Matt, around the charming old station. Matt meets the magical Mr. Conductor and Harry Cupper, the new engineer, and his granddaughter, Tanya, are also introduced.
- Does It Bite? - Tanya meets Mr. Conductor for the first time and become friends with him. Matt learns to overcome his fear and realizes that he should not be afraid of Harry.
- And the Band Played Off - Stacy made a mistake on the train schedule. This causes a train passenger to miss his train, and he gets very upset. Matt, Tanya and Mr. Conductor helped Stacy and made her realize that people often make mistakes, as long as they learn from them.
- Pitching In and Helping Out - Mr. Conductor shows the kids that a lot of nice things can be made with a ball of string. The kids use it to make decorations and help Schemer tie his shoes.
- Show and Yell - Matt and Tanya did a puppet show. It was not a success at first, but with the help of Harry, Stacy and Mr. Conductor, the kids learn that they should always try their best and never give up.
- Faith, Hope and Anxiety - The kids are sad because Harry could not take them fishing. Stacy cheers them up and told them not to let this disappointment ruin their day.
- Agree to Disagree - Matt wants to read a book, but Tanya wants him to play. They get into an argument. They learn that they can do different things and still be friends.
- Whistle While You Work - Schemer thinks that little jobs are not important. This causes him to have some problems and he later learns to take more responsibility.
- Two Old Hands - Mr. Conductor does not want to talk to Harry because he is afraid that Harry will not like him. Matt and Tanya encouraged Mr. Conductor to prepare a surprise birthday party for Harry.
- Happy Accidents - Matt and Tanya learn the importance of being careful to avoid accidents.
- Ring in the Old - Matt and Tanya learn to appreciate old people and realize that old people have a lot to share with young people.
- Impractical Jokes - Schemer likes to play jokes on people. When one of his jokes backfires, he learns that some times are better than others to play jokes.
- Finders Keepers - Matt and Tanya found a saxophone in the lost and found. When the concerned owner of the saxophone comes to the station to look for the instrument, the kids learn that it is wrong to take something that belongs to someone else.
- Just Wild About Harry's Workshop - Schemer wants to turn Harry's workshop into a snack bar. When his arcade broke down, he learns how important the workshop is. He realizes that without the workshop, Harry cannot fix his arcade.
- Promises, Promises - The train schedule is a mess, so Stacy and Harry work out a solution to present to J.B. King, Superintendent of the Indian Valley Railroad, at his office. Stacy reluctantly leaves Schemer in charge of the station and to take care of Matt and Tanya. As soon as they leave, Schemer breaks his promises and attempts to turn the entire station into an amusement park, resulting in Harry and Stacy into getting into serious trouble with Mr. King.
- Word's Out - When the railroad reduces the train schedule, everyone fears the station will be closed. Then the town gossip, Midge Smoot, comes to the rescue. Midge praises Shining Time Station for coming to her aid, forcing the railroad to change their mind and return the station to being a train stop on the line's timetable.
- Too Many Cooks - Schemer uses the wrong ingredients to make a sandwich spread for the mayor's party. The mayor got mad at Schemer, so Stacy and the kids help Schemer prepare a new sandwich spread.
- Mapping it Out - Matt and Tanya go on a train ride without telling anyone. This causes Harry and Stacy to worry a lot. The kids learn that they must always tell an adult where they are going.
- Things that Go Ga-Hooga in the Night - Everybody camps out at the station at night. Schemers plan to scare everyone backfires but he has another trick up his sleave.
- Is This the End? - A new big station has been built in Snarlyville and our friends at Shining Time Station are saddened when they learn of the decision by the Indian Valley Railroad to close the station. Stacy, Harry and the kids try to cope with the bad news while Schemer decides to fight back. Hopefully J.B. King will realize before it's too late just how special Shining Time Station is to everyone.
- 'Tis A Gift - It's Christmas at Shining Time Station and Schemer is at scheming as ever as he campaigns to be chosen as Santa's helper for the Indian Valley Gala Holiday Pageant. A mysterious elderly stranger by the name of Mr. Nicholas visits the station and seems to know a lot about the Shining Time Station residents.
- Mr. Conductor
- Stacy Jones
- Horace Schemer
- Harry Cupper
- Matthew Jones
- Tanya Cupper
- J.B. King
- Midge Smoot
- Mayor Osgood Bob Flopdinger
- One Man Band
- Mr. Nicholas
- Tucker Cooper
- Schemer's Mother (mentioned)
- Gracie Jones (mentioned)
- Ringo Starr as Mr. Conductor
- Didi Conn as Stacy Jones
- Leonard Jackson as Harry Cupper
- Brian O'Connor as Horace Schemer
- Jason Woliner as Matthew "Matt" Jones
- Nicole Leach as Tanya Cupper
- Susan Greenhill as a Passenger
- Russell Brown as the One Man Band
- Clinton Smith as Ed the Slit Man
- Karen Gersch and Barbara Rhind as the Acrobats
- Robert Hill as Tony the Mover
- Nathaniel Kaz as himself
- Wendy Brackman as herself
- Ardon Bess as Tucker Cooper
- Lloyd Bridges as Mr. Nicholas
- Judy Marshak as Claire
- Rachel Miner as Vickie
The Jukebox Band
- Craig Marin as Rex
- Olga Marin as DiDi
- Wayne White as Tex (1989)
- Jonathan Freeman as Tito Swing
- Alan Semok as Grace Bass (puppet; 1989) and Tex (1990)
- Peter Baird as Grace Bass (puppet)
- Kenny Miele as Grace Bass (puppet; 1990)
- Vaneese Thomas as Grace Bass (voice; uncredited)
- This is the only season where Matt, Tanya, and Harry Cupper appear as regular characters.
- The first Mr. Conductor only appears in this season.
- The Thomas stories were given their UK titles in the credits.