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.

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.

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.

Trace hits the road to record an album with his ex-girlfriend but has trouble channeling creative inspiration while he is away from Abby. A well-intentioned Jess creates trouble for Bree when she advertises that a famous author will attend a book reading at Bree’s new bookstore.

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.

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.

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.

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.

As the nightclub opening nears, Trace spends late nights practicing with Leigh and his band, while Mick fights city hall to receive a live music permit. Abby receives a promotion at work, but it leaves her with less time to spend with the family and Trace.

Abby learns her ex-husband is in a serious relationship navigates their new family dynamic. Abby misses Trace by her side as she explores the new co-parenting roles with Wes and his girlfriend. Pulled in many directions with work obligations, Trace misses out on family moments with Abby and the girls. Mick and Megan’s relationship continues to evolve, but is influenced by their past. Having worked independently for months, Jess adjusts to David’s return to the bed and breakfast. Also adjusting to a man in her life is Bree, who attempts to define her partially professional, partially romantic relationship with Simon. At the Chesapeake Shores Fire Department, Kevin enjoys a week of on-the-job training with Sarah. Meanwhile, Nell recruits Connor to investigate a contestant who is breaking the rules in an annual gardening competition, but a surprising discovery makes her rethink the plan.

Trace discovers that The Bridge has fallen into debt while he was on tour in and tries to repair the damage. Trace’s discovery prompts Mick to reconsider the terms of their partnership and to put aside friendship and family when business is at stake. Abby works to try and balance her stressful workload with being a “super mom” to keep up with Wes’ new fiancé. Jess is suspicious when David’s sister arrives in town looking for help with the business. Bree asks Nell to read her manuscript, but realizes the real test will come when she gives it to Megan. When Kevin doesn’t receive a job offer near Chesapeake Shores, Sarah considers relocating for a dream job. Facing relationship troubles of his own, Connor goes up against an ex-girlfriend in court. Meanwhile, Megan plays hardball when the mayor eliminates her job at the Arts Counc

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

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.

Abby is burdened by continued paparazzi attention from Trace’s growing fame. As he works through his loneliness while on tour away from Abby, Trace writes a song for Abby, which prompts an unexpected reaction from Leigh. Mick tries to repair his relationship with Connor at Megan’s insistence, but their tumultuous history makes Connor reluctant to reconcile. Kevin is concerned when Sarah seeks adventure after a near-death accident at work, noticing similarities between her behavior and his after his wartime injury. Bree edits her novel with Simon’s help, and realizes she and one of her characters share the same drive for self-preservation that stunts their relationships. Meanwhile, Jess fears her relationship with David is over.

Abby returns to her hometown after hearing troubling news about the family inn facing foreclosure.

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.

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 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.

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.

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.