In Nashville, Leigh talks to Trace about their music, but he cuts her off and asks if she really wants to work with Mark Hall. Suspicious, Leigh asks Trace if he is keeping anything from her. Trace insists he was just wondering what Leigh thought. Later on, Trace meets with Mark separately to ask, again, if he can keep Leigh as his singing partner. Mark stands by his word that it is Trace as a solo act or nothing at all.
Meanwhile, Abby signs up for the PTA and runs into an old friend from high school, Jackie, and the two engage in chit chat. Jackie sets Abby up with a PTA partner, a new father in town, Douglas Peterson. Together the two will be working on fall fair receipts. Later, when they meet up, they get to know each other, and Abby opens up about the difficulties of dating a musician.
Connor and Megan grab a cup of coffee at Sally’s Café when Connor runs into someone he knew from college, Danielle. She informs Connor that she actually accepted a job in Baltimore, so she will be living close by doing some pro bono work in Chesapeake Shores. Connor suggests the two get together for coffee while she is in town. When Danielle walks away, Megan leans in and tells her son that she likes her.
Gran finds an old treasure map that Bree made when she was a teenager, highlighting where Bree hid a time capsule in Chesapeake Shores. Later on, Kevin and Bree decide to participate in the treasure hunt and take it up on themselves to do some catching up about their personal lives.
Mick runs into Thomas at the Green Fair in Chesapeake Shores. Mick is angry to see his brother handing out pamphlets, questioning the development of what Mick will do with the O’Brien land. He is disappointed that Thomas has decided to air their dirty laundry to the public by distributing the brochures.
In Nashville, Leigh and Trace grab a beer to talk about recording at another studio. She stops Trace from saying anymore, since she has already heard through the grapevine that Mark wants Trace as a solo act. She encourages Trace to take the deal, because he has no choice. At this point, Mark owns their music since they signed the contract. Later on, Trace approaches the manager of a well-known showcase, Pete, and asks if he and Leigh can get a spot to perform. Pete agrees. Trace surprises Leigh with the news. Although she is hesitant to perform, Trace urges his partner just to trust him.
Abby gets a surprise visit at her office from her New York colleague, Jack, who stops by to tell how impressed the Manhattan office is with her work. Jack’s ears perk up when Abby tells him she met a new friend, Douglas, who she is working with on a PTA project. Jack tells Abby he knows Douglas from New York and he recently moved to Chesapeake Shores looking for a new beginning since his wife died the year before. Just as Abby is about to ask some follow-up questions, Jack has to take a phone call.
Connor meets with Danielle, and she is surprised he ended up at the firm he works at today in Baltimore. When Connor wants to know why, she tells him he is working for the evil empire that takes on cases that nobody else will touch. He responds that not every lawyer gets an outstanding opportunity to work for a firm that wants to protect freedom of speech like she does, but she believes he works for a firm that wants to end it.
As Abby and Douglas finish up their PTA project, she tells him she knows about his recent loss. Douglas tells his new friend he doesn’t like talking about it because it always makes people treat him differently, but Abby assures him that won’t happen with her.
Taking his mom’s advice, Connor heads to the Green Fair to visit Danielle, who is doing volunteer work. While there he runs into his Uncle Thomas, who wants to know if Connor is interested in pro bono work, himself. He says, no, he was just about to visit a friend.
After several hours of digging, Kevin finally finds the treasure box that Bree hid all those years before. He gets cheered on by his sisters who had more fun watching their brother do the physical grunt work.
Leigh and Trace prepare for their showcase, to be performed in front of industry insiders. She tells Trace thank you for sticking by her and he says he knows Leigh would do the same. John surprises the two and says if the offer still stands, he would love to play bass with his former band. Before they hit the stage, Mark cuts in and tells Trace that if the trio perform on stage he will make sure his album is never get released. Trace, Leigh and John walk right past him. Once on stage, Trace introduces the group as the Trace Reilly Band and they perform “Freefall.” Afterwards, they began schmoozing with industry big wigs as Mark watches from the sidelines.
At the Inn, Jess has a hard time with a difficult customer who she just can’t please. The next morning, Jess finds out that her tough customer is really a famous travel writer, Kenneth Shane, whose reviews are often featured in The New York Times. Now all Jess can hope is that he writes a decent review, considering all the times he complained during his visit.
Gran tells Thomas that she is extremely disappointed over Thomas’s decision to print brochures hurting Mick’s land deal. Mick surprises the two at the café and grabs a seat. Noticing his sly smile, Gran tells Mick that whatever plan of revenge he has against his brother, don’t do it. Mick informs his brother that the sponsor of the Green Fair got all the necessary permits for the event, except the one for its own booth, which means all of Thomas’s booths will be removed. Gran knows it was Mick who made the phone call earlier to get his brother in trouble.
When Kenneth’s review of the Inn comes out, David encourages Jess to read it out loud. She is pleasantly surprised that Kenneth loved the bed and breakfast, as well as the food that David prepared during his stay. Jess can’t wait to share the good news with the rest of the family.
In Nashville, Trace, Leigh and John bask in the success of the night before. Leigh wants to know what they are going to do about the album that Mark owns the rights to. Trace says to ditch that album; he wants the trio to record another album on an independent label.
Later, the family gathers around the fire pit to open Bree’s time capsule. Before opening the box, Bree hopes that the objects inside will represent memories that will bring a smile to the family’s faces and serve as a reminder that life can be simple and happy. The time capsule includes Bree’s journal, Kevin’s Christmas mints, Connor’s king crown, Bree’s watch, Mick’s dad’s flask, Gran’s childhood fairy ornaments and Jess’s stuffed animal that was given to her by mother. Seeing it all brings smiles to everyone in the O’Brien family.