After Mark offers Trace and his band a worldwide tour deal, Trace and Abby worry about how it might impact their future together. As Nell ponders a lost love from her past, Abby, Jess and Bree are faced with the possibility of losing their new loves in the present.

Abby and Trace seem finally ready to move forward; Jess, David and Bree attempt to untangle their complicated love triangle; an emergency phone call puts Trace in trouble with the law.

As season four comes to a close, Trace and the O’Briens face decisions affecting their personal and professional lives. Trace weighs his relationship with Emma against her musical potential. Abby and Connor consider new career paths, while a new agent has Bree questioning what’s next.

After his band’s video goes viral, Trace receives offers from music executives, but tries to convince his band to give Mark Hall another shot. Abby, Nell and Megan spend some family time together preparing a princess birthday party for Carrie.

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.

Trace makes a confession regarding why he left Nashville. Meanwhile, Megan confronts Mick about past mistakes responsible for pushing her away; and Abby learns the truth about the fraud investigation from a surprising source.

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.

Mick nervously faces a failing business deal; Abby is subpoenaed in the investigation against Wes; Kevin recovers from his fall at home while struggling to define his future with Georgia; Trace learns the warehouse property is still in reach.

Trace rethinks sharing ownership of The Bridge with Mick. Jay helps Abby reconsider her priorities. Jess and David find themselves hosting guests before they are ready. Connor pursues an intriguing new opportunity. Kevin and Sarah discuss their future. Bree prepares for opening day of her play.

Kevin's fiancée arrives in town, surprising the O'Briens. Meanwhile, Abby gets tangled in a fraud investigation; and Trace receives bad news about the water-house property he covets.

The play is in jeopardy, it's Abby and Trace to rescue. David and Jess learn to work together, Bree learns to work alone. Mick and Megan come together while Connor goes it alone. Kevin and Sara return with a surprise announcement.

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.

Jess and David host visitors in town for the traditional Snallygaster hunt. Mick and Thomas revisit a weekend-long hiking trip from their youth.

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.

When Evan comes to the house, he throws out his back and must recover for a few days on the O'Brien couch, connecting him with the family in a way Abby never anticipated.

A legend visits Trace as Megan plans Kevin's wedding; Jess and David discover their past can't be repaired, and Simon joins Bree as her play begins rehearsals

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.

Luke’s court case is here and Connor comes to his defense despite personal risks. Abby faces a romantic dilemma when Evan declares his true feelings and Jay wants more than friendship.

As Jess and David try to buy an inn, love and loss surround the O'Briens; Mick and Megan explore feelings; Kevin and Sarah make a decision that can upend the family; and Bree and Connor suspect true love might not last forever.

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.

Various issues are troubling the O’Briens. Mick is in denial about his addiction. Margaret passes the bar. Jess pursues a new idea, and Bree tries mending the rift between her and Luke.

Mick gets closer to the ones he loves while Evan and Luke push themselves away. Mick continues to rebuild his relationship with Megan. Luke recovers from a gunshot after stopping a robbery.

O'Brien Construction's eccentric billionaire client, Evan Kincaid, comes to town and throws Abby and Mick off their game. At a moment of triumph, Connor discovers his law firm is hiding information from him, and Megan discovers a lost painting that leads her to a famous, reclusive local artist who wants nothing to do with her.

Sarah and Kevin come together with exciting news. Connor and Margaret’s law firm struggles to make ends meet, and when Mick’s pill addiction starts to noticeably affect his life, the O’Briens must rally together and stage an intervention.

Evan finds himself wondering if he has feelings for Abby; Luke is threatened.

Kevin learns something new while David questions what he thought was true. Bree finds she and Luke share a birthday. Kevin discovers the gender of the baby. David confronts his father.