The multi-generational family drama follows Abby O’Brien (Ory), a high-powered career woman, divorcee and mother to twin daughters, who makes a trip from New York City to her hometown of Chesapeake Shores. Her visit home brings Abby face to face with her past, including her high school sweetheart Trace (Metcalfe), her uncompromising father Mick (Williams) and her esteemed grandmother Nell (Ladd). Abby realizes the toll her career has taken on her ability to be a hands-on mother to her daughters, and considers a permanent move to Chesapeake Shores.

As the 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 his music career in Nashville. Then, harboring resentment for both of her parents, Jess sets out to prove she doesn’t need their help to open a bed and breakfast of her own. But just as it seems this family can’t find common ground, an unexpected confrontation between Abby and her ex-husband Wes proves the O’Brien’s can come together in a crisis.

As the O’Brien family reunion weekend continues, it seems the family is peacefully cohabitating – but is it just the calm before the inevitable storm? Abby announces she’s making a permanent move to Chesapeake Shores to raise her daughters, and she contends with her brother Connor’s harsh judgement as she prepares to go to court to fight for custody. (Connor is currently in law school). As Abby and Trace agree to put any romantic feelings on hold, Trace struggles with upsetting news from his past in Nashville. And, finally, when Mick offers Bree to stay in Chesapeake Shores to overcome her writer’s block, she finds she’ll be making some big life changes of her own.

As Abby settles in and starts her job at her firm’s Baltimore office, she wonders if she can remain just friends with Trace. A beautiful woman, Leigh Corley, from Trace’s past in Nashville arrives unannounced to Chesapeake Shores, and she is determined to convince Trace to return to Nashville and his music career. Abby and Trace’s friendship is in question once Abby hears of this news. As Megan tries to repair her relationship with Connor in New York, the O’Brien family will receive upsetting and unexpected news that Kevin has gone missing while serving his last tour in the military.

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.

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.