Henry and Gordon complain about the cold January weather. They also argue about who truly deserves to pull the express, much to the annoyance of Edward and James, the latter of which has a mishap of spinning on the turntable due to the high winds. Even Percy tries to help by suggesting that Gordon and Henry share express duties, but they disgustedly oppose the idea. Henry also talks about a special fish train called the Flying Kipper, and how a good run with it could impress Sir Topham Hatt to the point where he would let him pull the express.
The express argument continues throughout the day, and Gordon even has slight trouble getting out of the station due to the icy rails. Percy also offers to shunt the Kipper, to which Henry reluctantly agrees.
Very early next morning, things get off to a rough start when Percy wakes everyone up way before it is time.
Later, on the way to the harbor, Henry gives Percy instructions on how to shunt the train. Henry is determined to make the best impression possible in hopes that Sir Topham Hatt will give him a week-long tenure of express duties. At the harbor, the harbor master advises Henry to let Percy bank the train on the steep hills and warns him about the icy rails. Henry agrees to Percy being a banker.
The vans noisily conspire to give Henry “a silly adventure”, but Henry is in no mood for their mischief and shuts down their plans with a death threat as he pulls out.
Eventually, Henry and Percy start the ascent up Gordon's Hill. The vans tease Percy to discourage him, but Percy tries his hardest, and he gets Henry and the train over the hill. An excited Henry thanks Percy and starts to pick up speed, but he does not notice that he has been diverted.
In a goods siding, James waits in the cold weather for Henry to pass so he can continue with his train. In the brake van, James' driver and fireman have delightful discussions over drinks of hot cocoa with Darrell, a guard who had a fiasco with Thomas leaving him behind at one point. Allen, James' driver, enjoys his cocoa during all this. The men eventually realize that the Kipper is due soon and should head back to James.
Then, there is trouble; the men realize that Henry has been accidentally switched onto James' line. They scramble out the brake van and run to safety. Henry panics when he notices the stopped goods train ahead, and his driver applies the brakes, but Henry already knows it is too late. Sliding on the icy rails, going much too fast to stop in time, Henry smashes into the van and ends up in a huge wreck. Many trucks and some Kipper vans are damaged in the process. James and Percy inspect the damage. Henry begs them not to tell Sir Topham Hatt and tries to convince them to just put him back on the rails and let him try to finish the journey with the surviving vans, but Percy, concerned for Henry's well-being, tells Henry that he needs help.
When broad daylight makes the crash site more visible, Sir Topham Hatt comforts Henry and tells him that he will be repaired at Crewe, a special place for sick engines. Henry is nervous at first, but Sir Topham Hatt assures him that everything will be fine. He explains that Henry will get a new shape that will include a bigger firebox, which will eliminate the need for any more Welsh coal. A hesitant Henry thanks Sir Topham Hatt and also thanks Percy for helping him. Before James takes Henry away, Sir Topham Hatt announces he is going on a short holiday. But that's another story.
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