As the town's annual lantern festival nears, Trace and each of the O'Briens attempt to put their own challenges aside so four generations of O'Briens can come together for the lantern festival.

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.

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.