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.