The O’Brien family has faced its share of triumphs and challenges. Get caught up with all the characters and their storylines before the premiere of Season 5 on Sunday August 15 at 8/7c!
Single mom Abby has left behind a hectic life in the city, choosing to live a simpler existence with her daughters in her childhood hometown of Chesapeake Shores. As she navigates professional opportunities and obligations, she makes a big decision to blow the whistle on Porter Financial. She suspects the Porter Fund is actually a Ponzi scheme, and as a result of exposing the company she is suspended from her job at Capital Management. After reporting to a deposition and getting an attractive offer from Hunter Drew and Associates to join them with a pay raise, Abby turns down the job to retain her integrity. After Derrick Porter is indicted, Abby is offered her job back with Del, but she is unsure about whether to return. To keep busy, she gets involved with the school play and meets the 3rd grade teacher, Jay. The two get to know each other. Before Trace left for a big music tour, Abby broke things off as she was unable to handle the distance and playing second fiddle to Trace’s true passion – his music. Trace tries to reconnect with Abby and restart their romantic relationship but she is evasive. The two finally meet on the beach and share a kiss, but their future is anything but certain.
After a six-month long music tour in Europe and Asia, Trace returns home with the hope of rekindling his romantic relationship with Abby. He seeks her out at home and finally connects with her on a morning run at the beach, but Abby is not ready to start again. He keeps himself busy by working at The Bridge, where he meets a young musician, Emma. Trace begins to mentor Emma and they collaborate on her songwriting. To their surprise the two share a kiss, but Trace immediately apologizes. To his dismay, he learns that Emma’s conditional management deal with Mark Hall was dependent upon Trace going out on tour with her. In a heartfelt conversation, Trace tells her that he has issues with trusting people and reveals some of the struggles he experienced on the road. He encourages Emma to follow her dreams and wishes her luck in Nashville. After offering to buy Mick out of his share of The Bridge, Trace decides his next step is to build a music studio in town. Trace makes his case again to Abby, hoping that they can reconcile and move forward together, and they share a passionate kiss at the beach.
In Season four, Bree finishes her new play. After meeting a handful of producers and not finding the right fit, she decides to work with Hannah who she feels will do amazing work with both directing and producing her play. Simon surprises Bree by arriving back in town, but the two are having trouble connecting and agree that they are both trying too hard. After a tender moment when Simon finishes reading Bree the ending of his book, they decide to part ways. After witnessing an argument about the new B & B between David and Jess, Bree decides to rewrite the ending of her play and is thrilled with the results. The opening day finally arrives and Bree’s play receives a standing ovation. She is extended an offer by Brian, Hannah’s agent, to represent her and to bring her play to London! Bree is thrilled to accept this new opportunity.
Jess receives devastating news about her bed & breakfast. It has been condemned due to a termite infestation and she is heartbroken at the loss. David’s parents, have offered to buy their son and Jess a new bed and breakfast in the town of Tanglewood and the pair accept the offer of a new beginning. After giving it a try, Jess has found that the Inn in Tanglewood just doesn’t feel right, and she wants to return to Chesapeake Shores to rebuild. David agrees and they find the perfect location to create something brand new. After a lot of hard work and attempts the couple finally win a bid and secure the new location. In the spirit of compromise, Jess and David field some design options by Connor and try to find a happy middle ground. To their surprise, guests show up early days before the officially opening of the Inn. Jess discovers an engagement ring in a kitchen drawer and is thrilled when David finally pops the question!
In the beginning of season four, Kevin seeks out help from his sisters about how to propose to Sarah. After struggling, he gets the courage to do so over a flat tire! Sarah is excited and agrees to marry Kevin. They share the big news with the family – the sisters volunteer to be bridesmaids and Megan is happy to help Sarah with wedding plans. However, the couple gets overwhelmed at all the fuss and try to find a way to simplify the experience. At a family dinner, to everyone’s surprise they announce that they went to City Hall and tied the knot. They host a wedding reception at the house to celebrate the momentous occasion with their loved ones. Looking to the future, Kevin and Sarah begin to discuss having children. They realize they have different ideas about creating their new family and need to seriously take finances into consideration.
Mick continues to be busy with his business ventures, and he finds himself dealing with both project and personnel challenges. He is accused of wrongdoing by his partner and discovers he may be facing criminal charges for activities he had no knowledge of. He seeks out his brother Thomas’ help in how to clear his name and decides to hire a PR firm to help his image. Meanwhile, he and Megan begin to scout out potential wedding locations for Kevin and Sarah’s wedding. As they do, romantic memories are rekindled and the two even share a kiss. Later at a family dinner, they share a tender gesture in front of everyone that surprises the four siblings. Megan decides she would like to start painting again, and Nell encourages her to involve Mick in opening a new studio. As the two continue to spend time together, they agree to take things slowly.
Connor has found himself questioning his choice of career, unsure that being a lawyer was the right path, professionally. When his uncle Thomas assigns him an exciting case, he has renewed enthusiasm and is determined to win in court. On the advice of his uncle, they decide to keep the case out of court. To their surprise, the other side settles and Connor gets a taste of victory. He strikes out and makes a pitch to secure a job at Denzer, Louis and Phelps. Connor tells Thomas about his new position but gets a warning that the lawyers at Connor’s new firm don’t watch out for each other. Romantically, Connor and Danielle decide that they just are not right for each other. Danielle is not comfortable with his large family, and for Connor that is a dealbreaker.