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.

As the whole O'Brien family reunites in Chesapeake Shores for the first time in years, Abby attempts to learn from her own father's mistakes to avoid missing out on her young daughters' lives. As she contemplates leaving Wall Street behind, her high school sweetheart Trace struggles to open up about the reason he left Nashville. Harboring resentment for both of her parents, Jess sets out to prove she doesn't need their help to open her bed and breakfast. But just as it seems this family can't find common ground, an unexpected confrontation proves the O'Briens can come together in a crisis.

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.

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. Written by Hallmark Channel

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. Written by Hallmark Channel

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. Written by Hallmark Channel

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.