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- "Hello, Connor. Fancy a race?"
"Please say no, please say no."
- ―Caitlin, Annie and Clarabel and Connor[src]
One day, Thomas is pulling his two faithful carriages Annie and Clarabel. Thomas is in a cheeky mood and keeps going much too fast and then much too slow. When Thomas arrives at the station, he realises that his joking has made him very late indeed.
Thomas leaves Annie and Clarabel at the Shunting Yards while he races off to do a job at the quarry. While he is away, Caitlin arrives to pick up her coaches. Charlie isn't paying attention and attaches Annie and Clarabel to Caitlin's coaches. Annie and Clarabel think Thomas is pulling them, until they see him entering the yard. Thomas tells the coaches that Caitlin is pulling them. Thomas shouts after Caitlin, but the speedy engine is already too far away to hear him.
Annie and Clarabel are going faster than they had ever gone before. Presently, Caitlin stops to say hello to Connor. Annie and Clarabel are happy to have a rest, but then they hear something that makes them tremble. Caitlin challenges Connor to a race and Connor agrees.
Meanwhile, Thomas is trying to keep up with Caitlin. Reaching the top of a hill, Thomas sees Caitlin heading towards the bridge to the Mainland. Thomas is worried; if Caitlin leaves Sodor, he may never get his coaches back.
Thomas races to bridge, but when it gets there, it is already up. When the bridge comes back down, Hiro is on the other side pulling Annie and Clarabel. He had rescued the coaches from Caitlin's high-speed train.
Soon, Thomas is back puffing up and down the line with Annie and Clarabel. Thomas apologises for all of his teasing and the coaches apologise for making a fuss about his speed.