When Billie Jo has to come up with a fourth for her double date with Junior Hocker and Junior's visiting friend Roger Budd, Kate suggests Bobbie Jo to her. Billie Jo doesn't think Bobbie Jo would be a good fit as she knows all the boys see Bobbie Jo as a book worm instead of a fun girl. Convincing Bobbie Jo may be more difficult as Bobbie Jo admits that she just doesn't feel comfortable around boys yet. She goes on the date, but comes home early saying she just can't compete with Billie Jo. Kate tries to teach Bobbie Jo how to flatter a man the way Billie Jo does. On her next date with Roger, things go much better.

A brochure made by Uncle Joe describing the incomparable Shady Rest Hotel of the future is accidentally mailed to The Centerville Sun Express travel columnist Gladys Stroud. In the brochure was the vision of what he hoped the hotel would one day be, including indoor ice rink, bowling alley, and swimming pool. Gladys decides to come and review the Shady Rest. Now the family has to scramble to keep her from finding out the truth and closing them down for lying. Despite their best efforts, Gladys finds out. Uncle Joe manages to sweet talk Gladys into not closing them down.

Herby is depressed when he gets drafted, so the girls cheer him up by suggesting he could be an astronaut. Uncle Joe hears this and decides he needs to promote Herby's future political career to the whole town. When Herby gets a discharge for minor medical problems, Kate finds a way for him to save face with Billie Jo and the rest.

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.

Billie Jo receives a $500 insurance endowment, which her late father set aside for his first-born to become a doctor. But Billie Jo wants to go to Hollywood to become an actress. Kate thinks that Hooterville's long time doctor, Dr. Depew, can talk Billie Jo into it. But Kate's thinks that Dr. Depew's handsome new assistant, Dr. Clayton Harris, would be able to convince Billie Jo even more. So using Uncle Joe as a patient with non-existing symptoms, Kate hopes to have Dr. Harris make a thorough examination with Billie Jo as his assistant, exposing her to the wonders of modern medicine. But, Billie Jo faints at the first sight of blood.

Billie Jo is still determined to use the $500 from her father to go to Hollywood to become a movie star. It doesn't help that Uncle Joe, who wants to go with her, is fueling her dream. Kate talks with Judge Drucker to see if she can legally prevent Billie Jo from going to Hollywood, but he advises against it. Dr. Depew believes Kate's mistake between Dr. Harris and Billie Jo was throwing them together in a professional relationship. He thinks they should throw them together in a doctor/patient relationship. First, they have to trick Billie Jo into thinking she's sick. Then, they have to get Dr. Harris to come by each day to check on her. Kate believes there is one more piece to complete the puzzle, courtesy of a fake edition of the Hooterville World Guardian.

When Kate unexpectedly sees Homer Bedloe in Hooterville, she knows trouble is in store. Bedloe plans on selling the Cannonball, a seemingly one-of-a-kind antique locomotive. His buyer is millionaire retired train man and antique train aficionado, Phillip Waterhouse. Waterhouse is an old, ornery and snobbish man who generally gets what he wants. With Charley and Floyd's help, Kate hopes she can convince Waterhouse that the train is in such disrepair that it's not worth buying. Kate's plan backfires when she learns Waterhouse enjoys repairing old trains. She hopes that with the family's help, she can get through to Waterhouse the necessity of the train to the valley.

Homer Bedloe is back in Hooterville trying yet again to find a way to shut down the Cannonball. He believes there must be something in the financial books since Charley and Floyd have not submitted a report in twelve years. That plan ends up being more confusing to Bedloe than it's worth pursuing. Meanwhile, Uncle Joe is given the task of digging a drainage ditch down by the tracks. He finds the lazy way to do it by advertising that guests can dig for silver down by the tracks. He figures others will do the digging for him. Bedloe decides to sell leases all along the track from Hooterville to Pixley for people to prospect for silver. In the process, all the digging will just rip up the track, leaving the train unable to run without major repairs to the track. Kate can see through Bedloe's scheme and she devises a way to outsmart him once again to keep the Cannonball running.

Uncle Joe gets angry at Charlie and Floyd when he is left behind by the Cannonball. He decides to start his own transport business by using Orville Miggs' "Flivverball", an old car converted into a railway car. At first the Flivverball is a success. Kate must now deal with the feuding groups before the Cannonball goes out of business.

Kate's former grade school teacher returns to Hooterville. Kate and her children reminisce how Miss Adelaide "Genghis" Keane was so strict on all the children, and she was a dreaded teacher. Kate and the girls are surprised to find that the elderly schoolteacher is no longer the tyrannical disciplinarian she used to be. They all get together to bring Miss Keane's confidence back. It doesn't take long for Miss Keane to become a disciplinarian again and Kate and the girls are beginning to regret what they did. Before Kate can confront her, Adelaide acknowledges that she has gone too far and is scaring people off. Kate finds a way for Miss Keane to be happy again.

Janet gives Kathy Jo a clean bill of health as the rash that she had has cleared. She figures Kathy Jo was allergic to something that isn't around anymore. But Kathy Jo's rash reappears when Steve returns from a week long business trip. Janet suggests Steve temporarily move out of the house to see if the rash clears while he's away. Then gossip spreads throughout the valley that Steve and Betty Jo have separated. Kathy Jo's rash clears up again. Steve is growing frustrated that he still can't go home. In the end, Janet figures out what is causing the rash and it isn't Steve.