When the Williams family decides to go on a family vacation, Kim suggests a road trip to Austin College and Dean proposes a stop at Disneyland; after meeting up with his old bandmates, Bill reflects on his life choices.

The Williams gather to celebrate Clisby's 75th birthday - including Bill's brother Melvin and his daughter Cassie. While Bill and Melvin try to one-up each other for Clisby's approval, Cassie shares big news with Lillian and Kim.

After Lillian's boss announces budget cuts, she is forced to make a decision and enforce boundaries between her personal and professional life. Meanwhile, Dean and Cory's friendship hits a few speed bumps as they work together for the boxcar derby. 

In search of a new hobby, Dean joins the drama club - only to find himself mixed up in drama of his own. Bill and Kim grapple with Bruce's choice to campaign for a local politician. 

After Bill befriends Dean's music teacher, Bill and Lillian attend a party at his house and the evening takes an unexpected turn. Meanwhile, with their parents away, Dean, Bruce and Kim make their own plans for the night. 

When Lillian joins the church choir, she discovers a new side to her mother-in-law. Later, Kim encourages a guilt-ridden Dean to have an encounter with the supernatural. 

Bill and Lillian consider moving into the first integrated neighborhood in Montgomery. Meanwhile, Dean develops a crush on Brad's mom during a sleepover at their house. 

As Kim decides to take classes at Bill's college and date one of his star students, Bill must walk the line between teacher and dad. Dean and his friends join the football team where Dean finds himself in a tricky situation.

Torn between his secret relationship with Keisa and his friendship with Broderick, Dean turns to Jackie for advice. Meanwhile, after her latest run-in with the law, Jackie decides to turn over a new leaf. 

It's the summer of 1969, and Dean and Bill are experiencing new walks of life in New York City where Dean has tagged along for Bill's career-making songwriting gig. Back in Montgomery, Lilian's infamous sister, Jackie, pays a memorable visit.