Uncle Joe starts a Free Wedding and Honeymoon Contest to promote business for the Shady Rest Hotel. Out of all the entries, one stands out: that of Laura Bentley and Tony Allison, a young couple whose parents will not allow them to get married. However, when they arrive at the hotel, they are actually an elderly couple whose respective grown children objected to their marriage. Kate and the girls still want to give them the best wedding and honeymoon the hotel has ever seen. Laura's daughter Violet, and Tony's son Herbert, arrive just in time to stop the wedding. Kate tries a little reverse psychology to get the bride and groom back on track. Kate's ploy has an unintended consequence which threatens not only the wedding but Laura and Tony's relationship altogether. In the end, Laura and Tony get married along with Violet and Herbert.

Note: This is the first one where Meredith MacRae plays Billie Jo.

Since she is now in junior college, Bobbie Jo thinks she's all grown up. She decides to go to an all night party with her friends. Kate refuses to let her go to the all-nighter, despite Bobbie Jo telling her that all the other mothers are letting their daughters go. Kate learns that none of the mothers want their daughters to stay out all night. Kate says Bobbie Jo can stay out until 01:30 and the Cannonball will be ready to pick the girls up at that time. Bobbie Jo and all the other girls plan to stay out all night anyway. Bobbie Jo and the girls decide to go home, but Kate has a surprise waiting for her and the others on the Cannonball.

There's a dance on Saturday. Billie Jo and Bobbie Jo will only accept a date from either Steve or Don, the new young doctor in the valley. Neither Steve or Don have asked anyone to the dance yet. Billie Jo believes she has the right of first choice being the oldest. Left out is Betty Jo, who feels she has the right to be included in the dating discussion. Not wanting to take it anymore, Betty Jo decides to strike out on her own by moving out and getting a job. Through a series of misunderstandings, Billie Jo and Bobbie Jo wind up going to the dance with Eb and Betty Jo shows up with Steve and Don. It's not long before the girls are paired off with the boys they should've been with all along.

It's the Christmas season, and everyone's in a rush to decorate the Cannonball in preparation for their annual caroling and gift delivery runs. Their plans are placed into jeopardy with the arrival of Homer Bedloe. He says that what they are doing is against railroad policy and he won't allow it. Kate hopes that Bedloe will have some heart, and she tries to use her best Christmas spirit in treating Bedloe with kindness to change his mind. Only Norman Curtis, the President of the Railroad, may be able to make Bedloe change his mind.

Bobbie Jo is ecstatic that the poem she submitted to a magazine has been accepted for publication. Sam ends up devoting the entire front page of the World Guardian to Bobbie Jo. The notoriety changes Bobbie Jo. She also starts hanging out with Stanley Harper, a beatnik, pseudo-intellectual from the coffee house crowd. Kate learns from Steve that the coffee house she is hanging out in, in Springdale, isn't quite what Kate had first imagined. Kate goes to see if it is a place suitable for Bobbie Jo. Kate finds a way to show Bobbie Jo that being a beatnik does not always equate to true art and intellectualism.

Betty Jo has been receiving a large number of floral bouquets, all signed "From an Admirer". Billie Jo and Bobbie Jo believe that the sender is probably one of the many boys she met on her travels. However, Betty Jo's admirer eventually make himself known and it's Eb. He is neither who Betty Jo expected nor wanted and she has to try to let him down easy. Against Kate's wishes, Bobbie Jo suggests to Betty Jo that she get Steve to act as her boyfriend to scare away Eb. The only problem with that plan is that Steve actually has feelings for Betty Jo. Kate manages to convince Eb that things wouldn't work out with him and Betty Jo. Meanwhile, Uncle Joe is trying to set up a labor saving luggage pulley system between the Shady Rest stop and the hotel's front porch.