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.

As Abby settles in at her firm's Baltimore office, she wonders if she can remain just friends with Trace; a beautiful woman from Trace's past arrives unannounced to Chesapeake Shores; Megan tries to repair her relationship with Connor in New York.

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.

As the town's annual lantern festival nears, Trace and each of the O'Briens attempt to put their own challenges aside so four generations of O'Briens can come together for the lantern festival.

When planning her cousin's wedding goes awry, Jess turns to an unexpected source-her mother, Megan-for help. An O'Brien family wedding has some unexpected tension when Mick is confronted by an adversary from his past.

In "Chesapeake Shores," each member of the O'Brien family is influenced by the past as they plan their futures in "All Our Yesterdays." Mick receives damaging information about Thomas, and considers whether to use it in their town hall debate over the family land trust. Jess plans a special meal to win David over, but is fearful to take the next step in their relationship. Just like Jess, Bree is afraid to move forward with her new admirer. Connor and Kevin both contemplate their careers, concerned they may be headed down the wrong paths. Overloaded with work, both Trace and Abby try to find time to spend with one another and their families. On advice from Nell, Megan tells her children the real reason she left for New York all those years ago.

Trace discovers that the general manager of The Bridge stole large sums of money. Abby realizes that she can't be a perfect boss, parent and girlfriend. David Peck's sister arrives, threatening Jess and David's relationship.

Battle lines form after Megan reads Bree's manuscript, Trace and Mick disagree over the future of the Bridge, with Jess's B&B's being devoured from within, and it appears that the same might be true with the O'Brien family.

After following his dreams to go on tour, Trace returns to an uncertain future with Abby. Kevin plans a special outing with Sarah. Though happy with her own relationship with David, running his family's inn together does not meet Jess's expectations. Fresh off penning a national bestseller, Bree meets with potential producers for a new play. Meanwhile, Mick discovers one of his contractors has engaged in suspicious business practices, and Connor questions his career path.

Trace's commitment to planting roots and winning Abby back is tested when a friend urges him to return to his music career. Abby puts her work life in jeopardy investigating a client's dubious business practices, and Connor also faces professional consequences after making an impulsive decision. Jess and David try to go back to where it all started. Bree worries that her chemistry with Simon does not live up to that of her autobiographical play's characters.