Continuity mistake: The children waving at Toby disappear after Toby puffs under the bridge.
Continuity mistake: Alicia Botti was annoyed by Toby's appearance. But in "Thomas, Percy, and the Squeak", she thought Percy being dirty was the proper appearance of a steam engine.
Answer: Butch the breakdown truck must have pulled Gordon's tender all the way up the rails so the breakdown train can reach it and also Butch helped to get Gordon close to the winch.