Abby thinks about leaving Wall Street; Trace struggles with his past; a confrontation.

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.

Trace returns to Abby after three months on tour, only to discover a family in turmoil. Bree's completed manuscript turns out to be a thinly veiled story of the family. Mick ends the fight over the family trust but begins a feud with Connor.

Nell tries to save the Wish Fountain. Abby discovers a never-opened letter that she sent to Trace. Mick inherits a sailboat and reunites with his brother Thomas. Bree welcomes an old friend back into her life.

Chaos reigns with the closure of The Bridge, the O'Briens are at war over Bree's manuscript, Kevin is heartbroken visiting Sarah's family in Philadelphia, and Trace realizes that he might not return to Chesapeake Shores.

Abby finally has to make a decision whether or not to break up with Trace for good. Bree's relationship with Simon is rocked when Caroline appears, and David and Jess have to finally figure out their relationship without the B and B.