"The Flying Kipper" (also known as "The Kipper Express") is the railwaymen's nickname for the overnight goods train, usually pulled by Henry, that carries fish from Tidmouth to the Mainland. James and Caitlin have been seen pulling the train.
At some point, instead of catching fish and taking it straight to Tidmouth in their boats, the fishermen at a small seaside village decided to have Thomas take it up in his trucks. One day, Thomas was delayed by a crate falling on him and eroded ballast underneath the rails, and by the time he arrived at Tidmouth the "Kipper" was long overdue; Henry was so cross at the delay that he deliberately ignored Thomas' warning about the rails. This meant greater haste was taken to couple the vans to the "Kipper", and by the time Thomas' crew had warned the yard manager about the rails Henry had left Tidmouth. Another attempt to warn a signalman down the coast failed when poor reception meant he was unable to hear the warning in time, and at last Henry ran off the rails and into the bay. It was not until morning that Henry and the vans were able to be rescued.
Until the sixteenth season, the "Kipper" seemed to have been scrapped in favour of taking fish from the seaside village in open trucks.
In the seventeenth season, when Caitlin was spending the night on Sodor, Henry decided to let her take the "Kipper" so they can have some sleep. However, she wasn't being considerate and she woke up all the animals at the Animal Park. Later, Henry challenged James to pull the "Kipper" but James tricked Henry into pulling it anyway, because of this the "Kipper" was late. The Fat Controller told James off and made him pull it the next night. At the docks, Cranky accidentally spilt some of the kipper on James.
- In an interview with Sodor Island Fansite, Steve Asquith explained that complaints about fish being carried in open trucks fell on deaf ears, due to the belief that children would understand a story better if they could see what was in the trucks. As a result, from the eighth season to the fifteenth season, all fish were carried unhygienically.