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.

Abby thinks about leaving Wall Street; Trace struggles with his past; a confrontation.

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 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.

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.

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.

School's back in session in "Chesapeake Shores," but a fresh start for some brings back old memories for others in "Photographs and Memories". As Abby sends her girls off to their first day at a new school, conflict arises between Trace and Wes about their roles in the family - complicated further by a Nashville recording label taking interest in Trace's new demo with a former flame. The O'Brien siblings reminisce over their own school days watching home movies shot by Megan, but these movies leave Jess feeling left out and angry at her mother for leaving when she was young. Nell helps Connor dress professionally for his new career - and adulthood - but struggles to prevent Mick from butting heads with his brother Thomas over family land. Like the rest of the family, Bree and Kevin attempt to bid farewell to their pasts to make way for future opportunities.

Chesapeake Shores is filled with music as the town awaits the grand opening of The Bridge nightclub in "Grand Openings". As the nightclub opening nears, Trace spends late nights practicing with Leigh and his band, while Mick fights city hall to receive a live music permit. Abby receives a promotion at work, but it leaves her with less time to spend with the family and Trace. Frustrated with her own work prospects, Megan (Barbara Niven) receives an endorsement from an unexpected ally. Jess begins to develop feelings for someone at work, while Bree is surprised at her bookstore by a new admirer - and famous author. Connor reconnects with former flame Danielle, and Kevin has eyes for a free-spirited firefighter. Sensing romance in the air, Nell hosts a dinner for her grandchildren and their new love interests.

A viral video and a birthday have two residents of "Chesapeake Shores" receiving special treatment in "The Royal Court." After his band's music video goes viral, Trace receives offers from music executives, but tries to convince his band to give Mark Hall another shot. Abby, Nell and Megan spend some family time together preparing a princess birthday party for Carrie. Kevin finds inspiration to follow his passion on a trip to visit one of his fallen army friends' mothers with Bree. Watching the shop in Bree's absence, Jess discovers that running a bookstore is not as easy as she thought. Connor turns to Danielle when he finds his career direction shifting. After Mick refuses to use incriminating information against his brother Thomas, he must find a new investor for his development deal.

Wes's new girlfriend reminds Abby that she might not be the only "mom" in Carrie and Caitlyn's life, and David and Simon's presence in Chesapeake Shores puts Jess and Bree in an unusual position.