On the night before Caitlyn and Carrie’s first day of school, the O’Brien family gather to watch old home videos. The videos are of a family tradition where, on the first day of school, each of the children talked about the experience and said that they wanted to be when they grew up. Before heading to bed, Megan promises her granddaughters that she’ll be back in the morning to record their big day.
The next morning, Abby confides to her grandmother that she’s nervous about the girls starting school in a new town. Gran assures her the girls will be fine and sends Abby off to take them to school. Stepping outside, Abby finds Trace is already there, wishing the girls luck on their first day. He also has a gift for each of them; a watch, so they’ll always know when it’s time to come home. Just then Wes arrives and, taking his cue, Trace leaves so the girls can go to school with their father.
Nearby, Jess is startled as she walks into the kitchen and finds her mom waiting for her. Business at the B&B has been slow since the Little Nell’s wedding. Megan wants to use her experience working at the Met to help her daughter create a new website for the B&B. Megan also thinks Jess needs a catchy new name and suggests “The Inn at Eagle Point.” To Megan’s surprise, Jess reluctantly agrees to her ideas.
As Wes and Abby walk the girls to school, Wes catches a glimpse of his daughter’s new watches. The girls cheerfully tell their dad that Trace gave them the watches as a gift for their first day of school. After the girls walk off to their classrooms, Wes turns to Abby and begins asking her about her relationship with Trace. He’s angry that Abby is allowing the girls to get close to Trace when he thinks Trace might not always be in the girl’s lives. Annoyed by the implication, Abby dismissively thanks Wes for his concern and walks away.
At Trace’s house, Leigh arrives to find out that Trace got a call feedback about their new single. A few days before, Trace and Leigh finished the last demo they owed their record label. Leigh is stunned to find out that not only were there no problems, but the label loved the song and are already looking for producers to help finish the single. Leigh is thrilled and leaps into Trace’s arms. The label also wants the two of them to return to Nashville as soon as possible.
Outside Sally’s, Mick finds his brother Thomas. The two chat politely, but Thomas knows their meeting is not by chance. Mick is still upset that his brother wants to use a tract of land in the O’Brien Trust to build a park in Chesapeake Shores. Thomas, a lifetime defender of the environment, doesn’t trust his brother to leave the land undeveloped. Mick is hurt but still, hopes he can change his brother’s mind.
At the farmer’s market, Kevin searches for vegetables when he runs into the firewoman who he met on the night of the car crash. The two exchange banter and are surprised by their unique chemistry. Searching the market for Kevin, Bree stumbles unseen on her brother’s interaction. As they walk home from the market she asks Kevin who the mystery woman is, but Kevin still doesn’t know her name. On their walk home, they pass by Bree’s favorite bookstore. Across the front of the store is a Large “Going out of Business” sign. Seeing this chapter of her childhood ending, Bree is overcome with sadness and grief.
On his first day at his new law firm, Connor arrives to immediate criticism from his boss about his choice of tie. His boss tells him the firm expects its employees to conform to a strict code of conduct. Connor quickly realizes this firm may not be the right place for him The next day, Connor confides to his grandmother that he isn’t so sure about the job. Nell offers to help Connor find a new wardrobe to help him make a great impression.
Nearby at the club, Abby meets Trace and he tells her about his new single and the recording session in Nashville. He promises her that he’ll be gone for just three days, but he also tells her that if the single is a hit, he may be gone longer on tour.
Later that night, Caitlyn and Carrie sit with their grandmother to film their video about their first day of school. When Megan asks them about their day, the girls both frown and tells her they want to go home to New York. Before school the next day, the girls tell their family that despite everything they tried, the other kids wouldn’t talk to them. Abby does her best to try and assure them that their second day will be better than the first.
Later in the day, Megan is helping Jess shoot a promo video for the B&B. Jess is having a hard time just being herself in front of the camera and her mother’s presence is only making things worse. Jess quickly reaches her breaking point and storms off. After some time, Jess walks into the kitchen and finds her mother photographing the flowers. Despite Megan’s efforts, Jess is still not ready to have her mother in her life. She lashes out at Megan, accusing her of trying to force her help on Jess. Jess tells her that help won’t be enough for Jess to forgive her for not being in there when she really needed her.
At Sally’s, Trace sees Wes sitting at a table and politely says hello. Wes remarks that he’s surprised to see Trace without his significant other, Leigh. Hoping to avoid confrontation, Trace turns to leave, but Wes continues to accuse Trace of making Chesapeake Shores his temporary home before taking off for Nashville again. Only this time, it’s personal for Wes because this time, his daughters are involved. Trace raises his voice, only to realize the argument is causing a scene. Before thing gets out of control, Trace turns and storms out.
Back at the club, Leigh and Trace are working on their new single. As they work through the song, Trace stops to ask if he and Leigh are still on good terms. Leigh assures him that their relationship is purely professional and that she has no plans of staying in Chesapeake Shores.
Later on that day, Bree asks Kevin about his relationship with Georgia. Kevin reveals that the distance has been hard on their relationship. Since they met in a combat zone, it was easier for he and Georgia to focus on the future and not the present. Now in the present, Georgia and Kevin have very little to actually talk about. Bree asks why Kevin keeps calling. Kevin reveals that Georgia asked him the same thing. He then tells Bree that Georgia’s decided to end the relationship and will be sending Kevin his things.
Later at the park, Jess and Abby sit and watch as the girls play. Abby tells Jess that thing have gotten better for the girls at school and they’ve now made many friends. Jess asks if Abby has any regrets about moving home, but Abby is sure she’s made the right choice. Abby then asks about Jess’s relationship with their mother. Jess tells her that she’s frustrated because their mother is only doing the things she wants to do at the inn, including making a website. Abby laughs and reveals to Jess that their mother doesn’t know anything about making a website. Megan called the IT department at Abby’s firm and has had them helping her through the process. Jess then realizes that she’s been wrong and that Megan is sincere in her desire to help her.
Back at the inn, Trace is helping with some repairs when Megan takes the opportunity to ask him if he plans on moving back to Nashville. He tells her no and assures her that his home is in Chesapeake Shores. As he answers her questions, Trace realizes that Megan is asking because she knows Abby is worried. Megan believes Trace is being sincere and suggests Trace try a more creative approach to easing Abby’s doubts.
In an open field on the O’Brien family trust, Thomas arrives to talk to Mick about the land. Mick wants to know why Thomas won’t just sell him his portion of the land and use the money for environmental causes. Unmoved by Mick’s idea, Thomas tells him that preserving the natural beauty of the land is more important than money.
Back at the B&B, Meg confronts Jess about their relationship. Megan knows she will never be able to explain what happened in the past but she promises her daughter that she’s not going away. She hands Jess a DVD, tells her that she loves her and leaves.
At the cemetery, Mick sits at his father’s headstone for a conversation with his dad. Mick tearfully tells his father how much he needs his advice right now. As he talks, the priest approaches Mick to offer him guidance. When asked how the priest knew he would be at the cemetery, the priest tells him that Thomas had been at the cemetery earlier having a similar conversation with their father.
Later in the day, Abby walks into Trace’s yard and finds Trace sitting at a table, set for a romantic dinner, complete with roses and champagne. As she takes in the scene, Trace tells her that while he’s unsure of the future, he’s certain that Chesapeake Shores will always be home.
Out on the beach, Kevin and Bree sit around a bonfire, preparing to burn mementos of their past. Bree tells Kevin that the fire is a metaphor for saying goodbye to the past and ushering in the future. For Kevin, this means saying goodbye to Georgia and making space in his heart for someone new. For Bree, this means letting go of Martin, Chicago, and the old bookstore. Bree reveals that she needed to take this step because earlier in the day, she signed the lease to take over the old bookstore. Kevin is surprised and happy for his sister’s new business and her new future. Their celebration is interrupted when the same firewoman from the farmer’s market approaches Bree and Kevin. She pulls out her pad and writes them a ticket for starting an illegal bonfire. As she hands Kevin the ticket, she winks at him and turns to leave. Kevin is perplexed until he sees her motion him to turn the ticket over. On the backside of the ticket, he sees that she has written her phone number.
That night at the B&B, Jess sits alone in the dark, clicking through the website her mother built. As she does, she begins to watch the DVD her mother left. On the disk is the first day of school video Megan made with Jess years before. In the video, when the young Jess is asked what she wants to be when she grows up, she responds that she wants to be just like her mom. Watching her younger self, Jess smiles as the tears flow down her cheeks.