As Kevin thinks about popping the question to Sarah, Trace goes back home to Chesapeake Shores. Meanwhile, Mick and Abby find out that their careers are in jeopardy, and David and Jess have second thoughts about their new B&B.
Abby has a tough decision to make, while Trace is urged by a friend to resume his music career. Elsewhere, rehearsals for Bree's play start, and David and Jess hark back to their past.
The planning of Sarah and Kevin's wedding doesn't go smoothly. Bree examines her romantic life, while David and Jess seek to buy an inn. Abby is pleasantly surprised.
Trace and Abby team up to save the play. In need of advice, Connor seeks the family's help. The O'Briens receive the huge news shared by Sarah and Kevin lukewarmly.
As guests show up at the B&B earlier than expected, Jess and David try to deal with the situation. Connor seeks to get a new job. Meanwhile, the O'Briens grapple with the decision of their parents.
As Abby and Jay go on their first official date, they run into Trace and Emma, and things get uncomfortable. Meanwhile, Bree examines her future, and David and Jess wait for the beginning of their life together.