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.

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.