Abby returns to her hometown after hearing troubling news about the family inn facing foreclosure.

As Abby settles in and starts her job at her firm's Baltimore office, she wonders if she can remain just friends with Trace.

Kevin's fiancée arrives in town, surprising the O'Briens. Meanwhile, Abby gets tangled in a fraud investigation; and Trace receives bad news about the water-house property he covets.

As Abby and the rest of the O’Briens prepare for the town’s annual lantern festival, Trace must return to Nashville to face a mistake from his past. Mick takes his granddaughters back-to-school shopping while covertly working on a business deal that is bound to cause family conflict.

Mick makes some unpopular business decisions when he plans to sell the nightclub that he and Trace had built together. When planning her cousin’s wedding goes awry, Jess turns to an unexpected source for help. Bree fights to regain control in the production of her play.

Mick receives damaging information about Thomas and considers whether to use it in their town hall debate over the family land trust. Jess plans a special meal to win David over but is fearful to take the next step in their relationship.

Trace discovers that The Bridge has fallen into debt while he was on tour in and tries to repair the damage. Trace’s discovery prompts Mick to reconsider the terms of their partnership and to put aside friendship and family when business is at stake. Abby works to try and balance her stressful workload with being a “super mom” to keep up with Wes’ new fiancé. Jess is suspicious when David’s sister arrives in town looking for help with the business. Bree asks Nell to read her manuscript, but realizes the real test will come when she gives it to Megan. When Kevin doesn’t receive a job offer near Chesapeake Shores, Sarah considers relocating for a dream job. Facing relationship troubles of his own, Connor goes up against an ex-girlfriend in court. Meanwhile, Megan plays hardball when the mayor eliminates her job at the Arts Counc

Abby develops an unexpected friendship with a client, while Trace faces conflict at The Bridge. Though initially hesitant to work with her ex-husband’s fiancé, Abby helps her out tremendously and builds a new rapport with her while on a project. Trace, however, has a more difficult time at work and considers putting his friendship with Mick in jeopardy during a professional disagreement. Kevin graduates from his EMT program, but the reality of he and Sarah moving apart looms over the happy occasion. When Connor’s ex-girlfriend offers him a job, he senses familiar romantic feelings developing. At Nell’s urging, Bree shares her manuscript with Megan and begins to realize there are two sides to every story. Meanwhile, Jess receives devastating news about the inn that she fears will impact her whole life – including her future with David.

Kevin mulls marriage with Sarah; Jess and David run their new B&B in Tanglewood; and Abby and Mick both discover that their careers are in jeopardy.

A legend visits Trace as Megan plans Kevin's wedding; Jess and David discover their past can't be repaired, and Simon joins Bree as her play begins rehearsals