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.