When Abby O'Brien was 17 years old, her mother, Megan, left her father, Mick, Abby and her siblings Bree, Kevin, Connor, and Jess. Sixteen years later, Abby, a successful career woman and divorced mother of twin daughters, Carrie and Caitlyn, lives in New York. Just when Abby is told her ex-husband Wes is getting remarried, her sister Jess asks her and the girls to visit Chesapeake Shores for a weekend. Abby is concerned upon learning Jess is renovating a rundown home into a bed and breakfast and is also needing help with finances. Returning home, Abby sees her high school sweetheart, Trace, now a successful country musician, whom she left to move to New York. Meanwhile, there is tension between Mick and Abby, stemming from him being a frequently absent parent when she was growing up and its negative impact on the family.
Nell returns home from a doctor visit, hinting there is something wrong but not wanting to discuss it. Abby jogs by Trace's place, and they briefly discuss last night and what it might mean. Soon after, Wes arrives to pick up the girls and gets into an argument with Abby. He gets in his car and says he'll be back in an hour. Abby returns to Trace, and they try to talk about each other's lives over the past several years. Trace won't open up about why he returned from Nashville, only saying that the music business isn't what he hoped it would be. As the two start to embrace, Abby stops and tells Trace the only way they can have a chance together is if her girls always come first and he lets things happen at her pace. As Jess prepares for the soft opening of her B&B, Megan takes a room there and the two later argue. A pipe bursts and Mick rushes to the B&B to fix it before the opening. Kevin, an Army medic, announces he's being deployed again to Afghanistan. Wes returns and hands papers to Abby, saying their current arrangement isn't going to work. Trace catches them arguing and starts toward Wes, but Abby tells him to butt out.
Abby decides to accept the job offer in the Baltimore office and stay in Chesapeake Shores to raise her daughters. She consults Connor, her soon-to-be lawyer brother, on the best way to fight for custody. Trace continues to struggle with things he left behind in Nashville, as evidenced by a heated exchange with someone on the other end of a phone call. Trace and Abby meet and agree that, for now, they need to be friends and nothing more. Mick suggests to Bree that staying in Chesapeake Shores for a while may be just what she needs to overcome her writer's block.
Just as Abby and Trace are getting comfortable with their "friendship" agreement, Trace's beautiful singing partner Leigh arrives unannounced from Nashville. Leigh tries to convince Trace to return to Nashville and finish the album they were working on, while Trace hints at problems he needed to leave behind. Leigh checks into Jess's bed & breakfast, leaving Jess and Bree to wonder if the relationship between Trace and Leigh went beyond music. Megan visits with Connor in his small apartment and tries to mend old wounds, but Connor's resentment is still very apparent. Nell convinces Mick to stop meddling in Jess's business, so Mick takes on a new project - building a playhouse for Abby's girls. Abby goes to see Trace at the diner, and catches him and Leigh smiling and laughing over a meal. At the end of the episode, Mick gets a call from an Army representative, saying that Kevin's unit in Afghanistan has gone missing.
Mick receives news regarding his son Kevin, who has been missing in action. This causes anxiety within the family. Trace tells his music partner, Leigh, he cannot return to Nashville to finish the album they started together. Mick and Abby travel to New York for her custody battle with her ex-husband Wes. Neither party can come to an agreement concerning their two daughters. The judge grants Abby temporary custody until an agreement can be made over the summer. Trace finds an abandoned warehouse for sale in town and dreams of turning it into a place for the townspeople to listen to music, with a studio upstairs. He then agrees to finish the album, as he needs the money, but he says when it's done, so will be his partnership with Leigh. She tries to kiss him, but he stops her. Mick receives another phone call saying that Kevin is alive and will be transported to a hospital. Mick and Nell discuss his father, who died in 1999. Mick wishes his children has the same feelings for him as he had for his father.
Out of nowhere, a woman named Georgia arrives at the house and says she is Kevin's fiancée. She has convinced the hospital to let Kevin recover at home. All the O'Briens want to tend to the injured Kevin, while also trying to figure out more about the mysterious Georgia. Abby is at work when an agent from the SEC shows up and asks what was in the boxes she transported home from New York. Not knowing what is going on, Abby calls Connor, who tells her to "lawyer up". Connor is otherwise occupied taking the bar exam, and starts to get romantic with his study partner. Bree tells Abby that while she was in Chicago, she found out Matt is seeing someone else. Trace's banker father tells him he has been rejected for a loan to buy the warehouse, saying there is nothing he can do to get around Trace's debts and lack of a steady job - also mentioning regular payments Trace is sending back to Nashville. Trace later finds out that Mick bought the building. At home in her room, Abby pores over the contents of her New York office, trying to figure out what spiked the interest of the SEC, while she watches a video of Trace and Leigh singing together.
Trace makes a confession regarding why he left Nashville. Meanwhile, Megan confronts Mick about past mistakes responsible for pushing her away; and Abby learns the truth about the fraud investigation from a surprising source.
As Mick nervously faces a failing business deal, Abby is subpoenaed in the investigation against Wes, and Connor comes up with a plan to prove her innocence. Kevin recovers from his fall at home while struggling to define his future with Georgia, before Jess opens up about a devastating event that could help them understand each other. And Trace learns the warehouse property is still in reach, but his long-held anger toward his own father could prevent him from finally realizing his dream.
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.