Abby O'Brien left her quaint hometown of Chesapeake Shores, and high school sweetheart Trace Riley, years ago for life in the big city. Now a high-powered career woman, divorcee and mother to twin daughters, Abby returns home & comes face to face with her past. As she reconnects with her uncompromising father Mick (Treat Williams) and her esteemed grandmother Nell (Diane 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. Based on the novels of the same name by New York Times bestselling author Sherryl Woods. A Hallmark Channel original movie.

As Abby contemplates leaving Wall Street behind, her high school sweetheart Trace struggles to open up about the reason he left his music career in Nashville.

As Abby announces she’s moving to Chesapeake Shores to raise her daughters, she contends with her brother Connor’s harsh judgement as she prepares to fight for custody.

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, Emma Rose, 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; 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.

The O'Brien family is stunned when Kevin's fiancée arrives in Chesapeake Shores; Abby is questioned in connection with a mysterious fraud investigation; Trace learns the warehouse property he has his heart set on is sold to an unexpected new investor.