In "Chesapeake Shores," each member of the O'Brien family is influenced by the past as they plan their futures in "All Our Yesterdays." Mick receives damaging information about Thomas, and considers whether to use it in their town hall debate over the family land trust. Jess plans a special meal to win David over, but is fearful to take the next step in their relationship. Just like Jess, Bree is afraid to move forward with her new admirer. Connor and Kevin both contemplate their careers, concerned they may be headed down the wrong paths. Overloaded with work, both Trace and Abby try to find time to spend with one another and their families. On advice from Nell, Megan tells her children the real reason she left for New York all those years ago.

With Trace still on the road, Abby and Trace find a way to combat the loneliness. With Simon in town, Bree has to define a new normal, as does Mick and Megan, who begin to suspect that old feelings never go away. Meanwhile, Sarah is injured on the job, and Kevin has to take a step back into his own past to help Sarah move forward.

Wes's new girlfriend reminds Abby that she might not be the only "mom" in Carrie and Caitlyn's life, and David and Simon's presence in Chesapeake Shores puts Jess and Bree in an unusual position.

Trace discovers that the general manager of The Bridge stole large sums of money. Abby realizes that she can't be a perfect boss, parent and girlfriend. David Peck's sister arrives, threatening Jess and David's relationship.