The Bradleys, Sam Drucker, Herby, Charlie and Floyd are decorating the Cannonball for its annual Christmas Eve trip of caroling, gift-giving and merriment around the valley. But, Homer Bedloe is determined to be a Scrooge and take possession of the train on Christmas Eve. Railroad President Norman Curtis finds out what Bedloe is up to and goes to Hooterville to stop him.

Bobbie Jo brings home Alan Landman, a mad-at-the-world young poet and slacker who has won her heart. Despite Bobbie Jo liking him in every respect, he dismisses her way of life. Bobbie Jo wants to prove him wrong, while deep down she wants to find out for herself if Alan is really right about how meaningless her conventional life is. The family's impression of Alan is quite dismal. Kate has to figure out a way to make Bobbie Jo come to the conclusion on her own that Alan and his life do not deserve to be romanticized.