Betty Jo has her first crush on a boy named Orville Miggs. But the object of her affections is more interested in tinkering with cars than he is in romance. As such, all Orville sees in Betty Jo is a mechanic's expert assistant. Kate doesn't want to see Betty Jo get hurt. Kate thinks he will see her in a different and more romantic light if she wears a dress and becomes a bit more feminine. But nothing they try makes Orville really notice Betty Jo, and ultimately give her her much wanted first kiss. If the family is able to accomplish their task, will Betty Jo ultimately think it was worth it?

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.

Charley begins to believe that everyone seems too busy to spend any time with him. Floyd has started to call on the widow Sarah Lawrence. Uncle Joe has a speech he has to prepare, so has no time to go fishing with him. Kate has far too much work to do around the hotel. Charley doesn't want to spend his time alone and miserable running the Cannonball. He decides to quit and move to the big city. Kate tries to manufacture ways of keeping Charley in the valley before his replacement Bill Tuttle comes and takes over his job. When Charley realizes how much he is loved and needed, he finds a way to talk Tuttle out of staying.

Kate receives a telegram from Railroad President Norman Curtis that he is sending Homer Bedloe with someone named Fred. Fred is actually Mr. Curtis' housekeeper's aged basset hound. Curtis believes Fred needs some good country air and space to re-energize himself. Curtis also hopes that Bedloe will soften his ways in the process. Bedloe comes up with the plan to "ruin" Fred and have him return to Curtis in worse shape than he arrived. That will hopefully sour Curtis' view of the Shady Rest and what it stands for. Kate figures out a way to bring back spirit to Fred and a way to break Bedloe's spirit.

An old friend of Kate's from high school is coming for a visit. Kate admits that she had a crush on H.J. Grant back then. His letter implies that he is now wealthy, and is coming back to the valley on personal business. Uncle Joe, however, believes that Herbie is a con artist after Kate's money. Uncle Joe decides he needs to break up any chance of a romance between Kate and Herbie. Orville finds a newspaper article that proves Herbie is wealthy. Now Joe wants Kate to marry Herbie. But Kate and Herbie want to remain just friends.