While Jess and Bree in Maine visit David and his fabulously wealthy family, Trace's role in Abby's family is questioned. Meanwhile, everyone helps out running the B&B and Wordplay, and Connor learns the truth about Danielle.

While Jess and Bree discover David's parents' secret plans, Abby joins Trace on tour, realizing that it will be impossible to stay clear of Trace's newfound fame. Thomas's vow renewal sparks Mick and Megan to re-examine their own relationship, as Connor reconciles with Kevin.

On the eve of the Chesapeake Shores Regatta, with Mick recruiting family members to join him on the water, Abby finally has to make a decision whether or not to break up with Trace for good. Meanwhile, Bree's relationship with Simon is rocked when Caroline appears, and David and Jess have to finally figure out their relationship without the B&B. In a surprise twist, a letter from Ireland might decide Nell's future.

As the O'Brien family welcomes Bree home from London they ruminate on how the past two months have changed them all. Kevin and Sarah try for a baby, Jess and David plan for their wedding, and Abby thinks back to her conversation with Trace after their kiss on the beach.

Abby reflects on the past and contemplates a future on her own terms. She and Mick deal with the damage to the reputation of O'Brien Construction, Jess struggles with something David's parents gave her, and Bree realizes two different men from her past may be returning to her life and her heart.

Jess and David's wedding is here, but the O'Brien family still has a lot to face before the celebration. Abby and Evan get into an argument over his hotel, threatening the entire project.

The O’Brien family comes together in the aftermath of Connor’s heart attack. Jess and David deal with media fallout after Dennis Peck goes on the run, and we finally discover who Abby called.

Abby goes all out to plan the perfect second date. David’s family makes a surprise visit to the B&B, and Megan must consider whether to take the job offer at the Getty or help Connor recover.