Billy Twofeathers' nephew, Kit, comes to visit the station. He runs into trouble when he accidentally breaks the window of the signal house. Meanwhile, Schemer's baseball team is practicing for an upcoming game. Kit decides to join the team, but is having a lot of trouble hitting the ball and does not feel too good about himself. He has a talk with an old man named Max who gives him some good advice. Max lived alone in the signal house and was a former baseball player. He teaches Kit how to play baseball and is a great source of inspiration for the young boy. When Kit is falsely accused of painting on the baseball scoreboard, he feels rejected and decides to leave. However, Max manages to stop Kit's train from departing the station. Meanwhile, Schemer's team is playing against the Snarleyville baseball team. After Schemer learns that his nephew, Schemee, is conspiring with the other team, he takes him out of the team. Now that his team is short one player, Schemer becomes desperate to find a replacement player, and eventually gives the spot back to Kit. Thanks to Max's advice, Kit hits a home run to give his team the win. Kit's relationship with his uncle Billy is also revived.
- Mr. Conductor
- Stacy Jones
- Billy Twofeathers
- J.B. King
- Midge Smoot
- Ginny Johnson
- Dan Jones
- Kara Cupper
- Kit Twofeathers
- Felix Perez
- Max Okowsky
- Tito Swing
- Tex and Rex
- Grace Bass
- Schemer's Mother (mentioned)
- Billy's Brother (mentioned)
- Thomas (mentioned)
- Duke (mentioned)
- Thomas tells the other engines the story of 3 little engines - Duke, Stuart and Falcon - who worked happily together on a small quarry line. Duke was old and proud, having been named after "His Grace". He enjoyed telling the younger engines how to properly behave and frightened them with the story of Smudger, a "rough rider" who went on to become a generator. But after years of service, the line was closed down and Duke was left alone in his shed when the younger two were bought by the Skarloey Railway. Over time, the shed was covered over by nature and Duke was seemingly forgotten. Percy is disappointed by this conclusion - but Thomas promises a happy ending, which will have to wait until next time!
- Thomas concludes his story, telling of how Sir Topham Hatt and some enthusiasts learnt about Duke and set out to find him. After days of searching, they almost gave up hope until one of them fell through the roof of the hidden shed. Duke was restored and brought to the Skarloey Railway where he was reunited with Stuart and Falcon, now Peter Sam and Sir Handel.
- The Portly Man
- Jem Cole
- Farmer Trotter (not named)
- Sir Topham Hatt (does not speak)
- The Mid Sodor Railway Manager (does not speak)
- Skarloey (cameo)
- Rheneas (cameo)
- The Boy's Father (cameo)
- The Inspector with the Bowler Hat (cameo)
- Other Mid Sodor Railway Engines (indirectly mentioned)
- The Duke of Sodor (mentioned)
Jukebox Band Song Segment
- Down in the Valley
- Skip to My Lou Medley
- Take Me Out to the Ball Game
- This is the first episode where Mr. Conductor interacts with the Jukebox Band.
- In this special, we find out that Didi has a crush on Mr. Conductor.
- Take Me Out to the Ball Game was re-used only with a different scenario.
- Bucky Hill joins the cast as Kit Twofeathers.
- Starting with this family special, Mr. Conductor's whistle and sparkle, and the Jukebox background music would have a lower sound.
- This is the second time that the outdoor scenes were taped in Tottenham, Ontario, Canada and mostly along the South Simcoe Railway (tourist).
- Engine No.136 and the Hudson-Hornsby 165DE diesel-electric shunter are used.
- Out of all the child characters in the special, Schemee went through the most change in appearance and voice. This is assumingly due to Jonathan Shapiro being the oldest in the child cast and having gone through puberty.