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- A young woman returns to her hometown to help save her sister's failing inn, where she contends with memories and faces from her past.
- A psychotic stalker gives a pregnant woman a labor-inducing drug, then kidnaps her newborn.
- An architect relives her disastrous wedding day over and over until she discovers what she really wants in life.
- After ten years, Mia hopes for a promotion to upper management in the store when the boss/owner wants to see her. But he wants her to show his son, Nick, the ropes. Mia's a widowed mom and Nick is single.
- A woman's one-night stand turns out to be her friend's husband, and a local political candidate.
- After following his dreams to go on tour, Trace returns to an uncertain future with Abby. Kevin plans a special outing with Sarah. Though happy with her own relationship with David, running his family's inn together does not meet Jess's expectations. Fresh off penning a national bestseller, Bree meets with potential producers for a new play. Meanwhile, Mick discovers one of his contractors has engaged in suspicious business practices, and Connor questions his career path.
- Trace's commitment to planting roots and winning Abby back is tested when a friend urges him to return to his music career. Abby puts her work life in jeopardy investigating a client's dubious business practices, and Connor also faces professional consequences after making an impulsive decision. Jess and David try to go back to where it all started. Bree worries that her chemistry with Simon does not live up to that of her autobiographical play's characters.
- The consequences of blowing the whistle on a Ponzi scheme begin to hit Abby so she tries to distract herself by volunteering during her leave from work where she meets an intriguing new man. Trace mentors Emma and encourages her to perform her music at The Bridge. Mick and Megan fear that the return of their romantic feelings will complicate their friendship. Fortunately, Nell is back in town as a confidant for Megan. Jess and David navigate a bidding war for a new B&B.
- 2016–202244mTV-PG8.2 (139)TV EpisodeWhile helping out on Cailtyn and Carrie's school play, Trace meets the new man in Abby's life and considers moving on himself. While trying to save his business, Mick falls into old habits of prioritizing work over Megan. In the wake of a big change in her personal life, Bree struggles to rewrite the ending of her play. Meanwhile, Kevin and Sarah share a big announcement with the O'Briens, which they receive with less enthusiasm than expected.
- After a stressful deposition, Abby reconsiders her priorities and the future of her career with Jay's support. Trace reaffirms his commitment to Chesapeake Shores when he offers to buy Mick's share of The Bridge. Jess and David receive guests at the B&B earlier than anticipated. Kevin and Sarah struggle to see eye to eye about what their future together holds. Meanwhile, Bree prepares for the premiere of her play, and Connor pursues a new job.
- 2016–202245mTV-PG8.3 (143)TV EpisodeAbby's official first date with Jay gets awkward when they show up to the same restaurant as Trace and Emma, revealing lingering chemistry between the former couple and causing Trace to reconsider recording a duet album with Emma. Meanwhile, family drama bubbles beneath the surface of O'Brien family celebrations. Standing at personal and professional crossroads, Trace and the O'Briens all have important decisions to make.
- Abby O'Brien, a high-powered career woman, divorcee, and mother to twin daughters, takes a trip from New York City to her hometown of Chesapeake Shores when she receives a panicked phone call from her younger sister Jess, who has renovated the charming Inn at Eagle Point. Her visit home brings Abby face to face with her past, including her high school sweetheart Trace, her undemonstrative father Mick who built the town, her daring sister Jess, and her beloved grandmother Nell. This trip also makes Abby notice the toll her career has taken on her ability to be a hands-on mother to her daughters.
- Abby thinks about leaving Wall Street; Trace struggles with his past; a confrontation.
- As the O'Brien family reunion weekend continues, it seems the family is peacefully cohabiting. but is it just the calm before the inevitable storm ? After Abby announces she's making a permanent move to Chesapeake Shores to raise her daughters, she contends with Connor's harsh judgment as she prepares to go to court to fight for custody. As Abby and Trace agree to put any romantic feelings on hold, Trace struggles with upsetting news from his past. And when Mick offers Bree a way to overcome her writer's block, she finds she'll be making some big life changes of her own.
- As Abby settles in at her firm's Baltimore office, she wonders if she can remain just friends with Trace; a beautiful woman from Trace's past arrives unannounced to Chesapeake Shores; Megan tries to repair her relationship with Connor in New York.
- The O'Brien family is stunned when Kevin's fiancee, Georgia, arrives in Chesapeake Shores, determined to take over as he returns home to recover. As Megan immediately clashes with Georgia's overbearing presence, Abby is questioned in connection with a mysterious fraud investigation. And when Trace's own father refuses to help him with a loan, he learns of a bigger betrayal as the warehouse property is sold to an unexpected new investor.
- Abby finds out the truth about the fraud investigation from an unlikely source, and suddenly realizes what it could mean to lose it all. As she turns to Trace, he'll confess to the life-changing reason he left his music career in Nashville. And as Megan confronts Mick about the mistakes that once pushed her away, Nell makes an announcement that will stun everyone, just as a horrible accident threatens to reverse all the progress they've made.
- 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 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 Kevin remains missing, Mick, Nell and the rest of the O'Brien family nervously wait for more news, while Abby goes to New York to fight for custody of her daughters. Despite Leigh's stubborn efforts, Trace continues to hide from his past, but a surprising new idea may have him returning to his music dream after all - if he can make a deal with his ex. And as the family gets the news they've been hoping for, Abby's court ruling will prove this family belongs together more than ever before.
- 2016–202244mTV-PG7.8 (233)TV EpisodeAs the town's annual lantern festival nears, Trace and each of the O'Briens attempt to put their own challenges aside so four generations of O'Briens can come together for the lantern festival.
- When planning her cousin's wedding goes awry, Jess turns to an unexpected source-her mother, Megan-for help. An O'Brien family wedding has some unexpected tension when Mick is confronted by an adversary from his past.
- School's back in session in "Chesapeake Shores," but a fresh start for some brings back old memories for others in "Photographs and Memories". 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. The O'Brien siblings reminisce over their own school days watching home movies shot by Megan, but these movies leave Jess feeling left out and angry at her mother for leaving when she was young. Nell helps Connor dress professionally for his new career - and adulthood - but struggles to prevent Mick from butting heads with his brother Thomas over family land. Like the rest of the family, Bree and Kevin attempt to bid farewell to their pasts to make way for future opportunities.
- Nashville is calling Trace, but leaving town creates a difficult distance between he and Abby. Trace hits the road to record an album with his ex-girlfriend Leigh, 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. Ready to move on from his past relationship, Kevin tries to impress a free spirited firefighter on their first date. As Mick continues his plans to develop family land, Nell attempts to have him reconcile with his brother, Thomas.
- In "Buried Treasures," the O'Briens dig up the past - both literally and figuratively - on "Chesapeake Shores." 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. At her bed and breakfast, Jess deals with a high maintenance customer, but gets more than she bargains for when his true identity is revealed. Mick and Thomas continue to spar over a family land development deal, never seeing eye-to-eye about the past or the future. Megan reconnects with the family by giving Connor dating advice and tutoring her granddaughters.