When her younger sister calls her for help with her B&B business, Abby O’Brien packs up her twin daughters and returns to her hometown of Chesapeake Shores to help. A high ranking executive with a top tier New York investment company, Abby intends to stay only for the weekend -- but reconnecting with her former boyfriend, Trace, may inspire her to radically reconfigure her life. At the same time, her fractured family is also coming together for a long-overdue reconciliation.

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.

Connor chimes in with legal advice as Abby fights her ex-husband Wes on his petition for full custody of their girls. Trace is trying to get construction completed on the church but bumps heads with Mick over who knows Abby best. Bree tries to convince Jess to let Megan back into her life, but Jess being the youngest, feels too betrayed by her mother’s exit years ago.

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

Tension is high among the O’Briens while waiting for news about Kevin’s missing unit. Abby leaves the girls with Nell as she and Mick fly his plane to New York for the child custody hearing. Leigh tries to convince Trace to come back to Nashville so they can pick up where they left off. Trace resists, and reminds her of the mistakes he made there that still haunt him.

As the O’Briens await Kevin’s return, a woman named Georgia shows up at the house and introduces herself as Kevin’s fiancé. The family is shocked to hear that Kevin is engaged but happy that as a trauma doctor, she’s qualified to nurse him back to health when he arrives. The federal government shows up at Abby’s job to investigate her.