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.
Chaos reigns with the closure of the Bridge, and the O'Briens are at war over Bree's manuscript. Meanwhile, Kevin is heartbroken visiting Sarah's family in Philadelphia, especially after he's offered his dream job back in Chesapeake Shores. When Trace realizes that he might not return to Chesapeake Shores, his relationship with Abby is cast into doubt, as Jess wonders if her relationship with David can survive without the B&B.
Battle lines form after Megan reads Bree's manuscript, and Trace and Mick disagree over the future of the Bridge. With Jess's B&B's being devoured from within, it appears that the same might be true with the O'Brien family.
Trace discovers that the general manager of The Bridge stole large sums of money, pitting Trace and Mick against one another. At the same time, Abby realizes that she can't be a perfect boss, parent and girlfriend, and David Peck's sister arrives, threatening Jess and David's relationship. Meanwhile, Connor rediscovers Danielle, and Kevin accepts that he might lose Sarah.
Boyfriend and girlfriend problems abound: While Wes's new practically perfect girlfriend reminds Abby that she might be the only "mom" in Carrie and Caitlyn's life; David and Simon's presence in Chesapeake Shores puts Jess and Bree in an unusual position; and Mick and Megan finally come to terms with the direction of their relationship. Meanwhile, Nell enlists Connor's help when she discovers that her rival in a flower show is cheating.
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.
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.
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.
With a nod to the past: Nell tries to save the Wish Fountain; Abby discovers a never-opened letter that she sent to Trace; Mick inherits a sailboat and reunites with his brother Thomas; and Bree welcomes an old friend back into her life. After Kevin witnesses a secret hug, Connor's future is thrown and Jess's future beckons with an invitation from everyone's favorite chef.
Just in time for the Chesapeake Shores Oyster Festival, Trace returns to Abby after three months on tour, only to discover a family in turmoil: Bree's completed manuscript turns out to be a thinly veiled story of the family, and Mick ends the fight over the family Trust but begins a feud with Connor after a fateful mistake.