Abby O'Brien Winters returns to the Maryland town her father built when she receives a panicked phone call from her younger sister Jess, who asks for her help to keep her inn from foreclosing.
As the whole O'Brien family reunites in Chesapeake Shores for the first time in years, Abby attempts to learn from her own father's mistakes to avoid missing out on her young daughters' lives.
Bree finishes her play, Kevin mulls proposing to Sarah, Jess and David realize their new B&B might not be right for them. Abby and Mick discover that their careers are at risk as is Abby's new life when Trace gets home from tour.
Trace is visited by a legend as Megan plans Kevin's wedding. Jess and David discover their past can't be repaired, Bree is joined by Simon as her play begins rehearsals. Connor and Abby make decisions that affect their careers.
The play's in jeopardy, it's Abby and Trace to rescue. David and Jess learn to work together, Bree learns to work alone. Mick and Megan come together while Connor goes it alone. Kevin and Sara return with a surprise announcement.
As Jess and David try to buy an inn, love and loss surround the O'Briens. Mick and Megan explore feelings, Kevin and Sarah make a decision that can upend the family. Bree and Connor suspect true love might not last forever.
