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.

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.

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

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 work continues on his hotel, Evan and Abby learn a bit more about each other. Evan stays a night at Jess's B&B.

Kevin mulls marriage with Sarah; Jess and David run their new B&B in Tanglewood; and Abby and Mick both discover that their careers are in jeopardy.

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

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.

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.

Kevin and Sarah try to keep a secret while Bree discovers one from Luke’s past. Evan whisks Abby away on a business trip, but his intentions are not what she originally thinks.

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.

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.

Away from the distraction of technology, Abby and Trace talk about their past and the future during a camping getaway. With some encouragement from Nell, Mick and Thomas try to work out their differences in person.

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.

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.

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.

As Kevin remains missing, Mick, Nell and the rest of the O'Brien family nervously wait for more news; Abby goes to New York to fight for custody of her daughters; Trace continues to hide from his past, but a surprising new idea may have him returning to his music dream after all.

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.

Abby decides to stay in Chesapeake Shores and fight for custody of her daughters. Trace deals with troubling news concerning his past in Nashville. Mick suggests that Bree remain in town in order to get over her writer's block.

As Abby settles in and starts her job at her firm's Baltimore office, she wonders if she can remain just friends with Trace.

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.

As Abby and the rest of the O’Briens prepare for the town’s annual lantern festival, Trace must return to Nashville to face a mistake from his past. Mick takes his granddaughters back-to-school shopping while covertly working on a business deal that is bound to cause family conflict.

Mick makes some unpopular business decisions when he plans to sell the nightclub that he and Trace had built together. When planning her cousin’s wedding goes awry, Jess turns to an unexpected source for help. Bree fights to regain control in the production of her play.

As Abby sends her girls off to their first day at a new school, conflict arises between Trace and Wes about their roles in the family—complicated further by a Nashville recording label taking interest in Trace’s new demo with a former flame. Mick butts heads with his brother over family land.

Nell discovers a treasure map that Bree made as a teen, leading Bree and Kevin to hunt for a family time capsule in the backyard. While Trace is in Nashville fighting his producer Mark Hall to keep Leigh on an upcoming album at the risk of his own career, Abby meets a handsome widower in the PTA.