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.

School's back in session in Chesapeake Shores, but a fresh start for some brings back old memories for others in Photographs and Memories. As Abby sends her girls off to their first day at a new school, conflict arises between Trace and Wes about their roles in the family - complicated further by a Nashville recording label taking interest in Trace's new demo with a former flame. The O'Brien siblings reminisce over their own school days watching home movies shot by Megan, but these movies leave Jess feeling left out and angry at her mother for leaving when she was young. Nell helps Connor dress professionally for his new career - and adulthood - but struggles to prevent Mick from butting heads with his brother Thomas over family land. Like the rest of the family, Bree and Kevin attempt to bid farewell to their pasts to make way for future opportunities.

Nashville is calling Trace, but leaving town creates a difficult distance between he and Abby. Trace hits the road to record an album with his ex-girlfriend Leigh, but has trouble channeling creative inspiration while he is away from Abby. A well-intentioned Jess creates trouble for Bree when she advertises that a famous author will attend a book reading at Bree's new bookstore. Ready to move on from his past relationship, Kevin tries to impress a free spirited firefighter on their first date. As Mick continues his plans to develop family land, Nell attempts to have him reconcile with his brother, Thomas.

In Buried Treasures, the O'Briens dig up the past - both literally and figuratively - on Chesapeake Shores. Nell discovers a treasure map that Bree made as a teen, leading Bree and Kevin to hunt for a family time capsule in the backyard. While Trace is in Nashville fighting his producer Mark Hall to keep Leigh on an upcoming album at the risk of his own career, Abby meets a handsome widower in the PTA. At her bed and breakfast, Jess deals with a high maintenance customer, but gets more than she bargains for when his true identity is revealed. Mick and Thomas continue to spar over a family land development deal, never seeing eye-to-eye about the past or the future. Megan reconnects with the family by giving Connor dating advice and tutoring her granddaughters.

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.

A viral video and a birthday have two residents of Chesapeake Shores receiving special treatment in The Royal Court. After his band's music video goes viral, Trace receives offers from music executives, but tries to convince his band to give Mark Hall another shot. Abby, Nell and Megan spend some family time together preparing a princess birthday party for Carrie. Kevin finds inspiration to follow his passion on a trip to visit one of his fallen army friends' mothers with Bree. Watching the shop in Bree's absence, Jess discovers that running a bookstore is not as easy as she thought. Connor turns to Danielle when he finds his career direction shifting. After Mick refuses to use incriminating information against his brother Thomas, he must find a new investor for his development deal.