Trace and Abby have a picnic in the park, where he serenades her with a song. When Trace leans in to ask Abby a question, he is interrupted by Caitlyn and Carrie, who ask him to play on the playground. He gives Abby a quick kiss and joins in on the fun.
The family is gathered around the table to listen to Meg’s speech for the art walk. Afterwards, Bree brings out an old portrait she found in the attic and wonders who the mystery man in the picture is. Gran seems to recognize the man in picture but plays it off like she doesn’t.
The Trace Riley Band is rehearsing for the art walk when John speaks up about his frustrations. He is ready for the band to start making money and playing free art walks isn’t doing the trick. John also points out that Trace isn’t making any of his own sacrifices for the band, considering they play music at Trace’s club, in his hometown, so he can be close to Abby. The band finally votes to call Mark back in Nashville and negotiate a deal.
Connor comes clean with his dad about working for Thomas. Instead of being upset, Mick offers his support to his son but also says the fact Connor had to hide the new job from his dad says a lot about their relationship.
Abby presents Douglas with all the paperwork he needs to take over the O’Brien land trust. He asks her point blank if she thinks this is a good deal. Abby is taken aback by the question but Douglas knows Abby as a straight shooter. He wants to know the reason why Matt Fox abandoned the trust. She promises Douglas that it is a great deal.
Kevin runs into Sarah and fills her in on his new apartment and his paramedic training. She lets Kevin know she is busy setting up the booth for the art fair, and asks if he wants to help her out. His reply is an easy smile.
Later on that evening, Abby and Trace are at the club when Mark stops by with some big news for the band. Mark got the group a six-month tour opening for Neil Brooks, which means traveling coast to coast and then playing in Europe! Abby is less than thrilled with the news.
Bree is having coffee with Simon and expressing her concerns that her manuscript due date is coming up. The two are interrupted by Jess, who tells them about David quitting the inn and possibly breaking up with her to spend more time with his family. The attention turns to Kevin who has joined the table and reveals he is afraid he was friend-zoned by Sarah.
When Mick and Thomas meet to discuss the trust, Thomas lets his brother know he found out Matt Fox backed out of the deal. Mick assures his brother that the deal will continue without Matt. Thomas also brings up that he knows Connor came clean to Mick about his new job. Thomas wants to stop fighting with his brother, and Mick takes it as his cue to walk away.
Meg is rehearsing her art walk introduction speech to Abby and Gran and accepting feedback. Later, Abby fills the two women in on Trace’s upcoming tour. Meg encourages her daughter to see the positive of it all and to not wallow in the negative.
After having a talk with Mark, Trace decides to pull the plug on the impending tour. He later tells Abby he made the decision after realizing he had too many responsibilities in Chesapeake Shores, including the club.
Jess and Bree sit down together to interview a new chef, as David looks on. As they all talk, Jess realizes just how much work David does around the inn for such little pay. Finally, David comes clean that he is the son of Dennis Lyle Peck, a wealthy Boston businessman; he comes from old money. Jess immediately wants to know why David is working at the inn and living in such a small apartment. He tells the sisters that he wanted to make it on his own, and he always wanted to be a chef instead of sitting in company board meetings. The reason why he is taking time off is to care for his dad, who is in poor health.
Douglas meets with Mick and Abby to discuss the land trust. Douglas admits he has heard there is bad blood between Thomas and Mick and wants to make sure Mick won’t have a problem going through with the development of the land, despite his brother’s objections. Mick shakes his hand the men have a deal.
Abby fills her sisters and Gran in on Trace’s decision to stay in Chesapeake Shores instead of tour. Gran, Jess and Bree all express their disapproval of Trace’s decision, because it means he is giving up his lifelong dream for his relationship, and that can lead to resentment later on.
The next day, Bree continues giving Simon the cold shoulder and he wants to know why. He assures her that he not any of her ex-boyfriends and he would never try to change her. She tells him her problem is that Simon took over her writing career by submitting her manuscript without her permission. He apologizes and asks for one more chance. She leans in and gives him a kiss, but says she needs to stick with her decision to move on.
Back at the inn, David is giving cooking lessons to Jess. He tells her the inn is going to be okay, but she tells him that doesn’t mean she will be. He wraps her in a hug. Jess makes David promise her that when he leaves, he won’t say goodbye; because she doesn’t do goodbyes well.
Abby and Trace find some alone time to talk about their relationship. Abby says she knows Trace would do anything for her and the girls, but she needs to encourage him to follow his dreams. Trace says he loves her and says he doesn’t think he can handle losing her, again. She tells him if they were meant to be, it won’t be the end.
At the art walk, Thomas and Mick have an exchange of words. Thomas tells Mick he is heading back to California for work, while Mick tells Thomas he is packing to fulfill a childhood dream of visiting Peru. He also lets Thomas know that he brought on a new investor for the land trust, throwing Thomas’s California plans out of whack.
Jess, Abby and Bree sit down on a bench at the art walk, staring at the black and white framed photo that Bree found earlier. Each sister is also reveling in their latest relationship busts and wondering if their lives are just better without men.
Meg takes the stage of the Art Walk. Taking Gran’s advice, she gives a speech from the heart and receives warm applause from the audience. She then introduces the Trace Riley Band to the enthusiastic crowd. While the music plays, David kisses Jess on top of the head and slips away in the crowd, while Kevin gets an email on his phone telling him he has been accepted to Stanford’s School of Medicine. Abby just watches Trace perform with tears in her eyes.