Abby O'Brien Winters returns to the Maryland town her father built when she receives a panicked phone call from her younger sister Jess, who asks for her help to keep her inn from foreclosing.

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 the O'Brien family reunion weekend continues, it seems the family is peacefully cohabitating, but is it just the calm before the inevitable storm?

As Abby settles in and starts her job at her firm's Baltimore office, she wonders if she can remain just friends with Trace.

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.

The O'Brien family is stunned when Kevin's fiance, Georgia, arrives in Chesapeake Shores, determined to take over as he returns home to recover.