Trace (Jesse Metcalfe) and Abby's (Meghan Ory) diverging paths finally meet as season four of "Chesapeake Shores" comes to a close in "Watercolors, Wishes, and Weddings". Abby's official first date with Jay (Greyston Holt) gets awkward when they show up to the same restaurant as Trace and Emma (Lanie McAuley), revealing lingering chemistry between the former couple and causing Trace to reconsider recording a duet album with Emma. Meanwhile, family drama bubbles beneath the surface of O'Brien family celebrations. In the early stages of their new relationship, Mick (Treat Williams) and Megan (Barbara Niven) try to avoid the relationship mistakes they made the first time around.
Jess (Lacy J. Mailey) and David (Carlo Marks) hit a snag in their B&B opening that threatens to derail David's romantic plans. When a potential new agent approaches Bree (Emilie Ullerup) about her goals, she realizes she is uncertain about what she wants to do next. Kevin (Brendan Penny) and Sarah (Jessica Sipos) try to find common ground for their future. Both Connor (Andrew Francis) and Abby consider new jobs. Standing at personal and professional crossroads, Trace and the O'Briens all have important decisions to make.
