The O’Brien family has faced its share of triumphs and challenges. Get caught up with all the characters and their storylines!
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, and the pair ultimately decides to go their separate ways. Abby focuses her attention on the family business, and Mick names her President of O’Brien Construction. A high profile and eccentric new client, Evan Kincaid, keeps Abby on her toes as she runs point on his hotel project in Chesapeake Shores. As progress is made with the build, Evan gets to know more members of the family and seems to want a closer connection with Abby. Jay too, lets Abby know he would like to pursue a romantic attachment with her. Who will Abby choose?
Billionaire Evan Kincaid plans to develop a hotel in Chesapeake Shores with the help of O’Brien Construction. Evan is charming but eccentric, swinging back and forth over the decision to move ahead with the build. After Abby convinces him to continue forward, the two make their way through unexpected roadblocks in the project, and Abby is never quite sure what to expect from the new client. As time passes, a lonely Evan shows an interest in getting closer with the O’Brien family and eventually lets Abby know that he would be interested in dating her. Will a romance blossom between the two?
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 jump into a new professional adventure. In season five, Bree arrives back from London tired but excited to find out about that the University of Maryland has offered her the chance to be their playwright in residence. Her high school nemesis, Jerome, is also involved with the University, which gives Bree pause. She moves ahead and works on creating curriculum for a creative writing course and she and Jerome come to a new understanding. She runs into her old high school crush, Luke, and the two share a natural chemistry. Will their relationship develop into something significant?
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 Season five, the couple continues to work on their beloved inn and find ways to work through challenges together. Their wedding day arrives and Bree officiates the ceremony.
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. In season five, Kevin and Sarah continue their journey to try to become parents. They are disappointed when Sarah is told she has endometriosis and may never be able to have children of their own. Sarah does find out she is pregnant, but the outcome is not what they dreamed of.
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. When a thrift store painting from artist Arthur Driscoll shows up in Megan’s life, she finds herself on a mission to locate the artist and showcase his work. Mick continues to work through legal challenges with O’Brien Construction, but is happy to have Abby by his side. Mick and Megan further solidify their relationship while supporting their grown children during important milestones.
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. In Season five, Connor is making strides in his law firm, and meets an extraordinary paralegal, Margaret. She advises Connor to keep his desk with sensitive information locked, and Connor begins to grow uneasy. He ultimately decides to resign and launch his own law firm in town. Things are going well until an unexpected health crisis for Connor shocks the entire family.
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. To Trace’s dismay, Abby insists they want different things for their future and they cannot find common ground. Trace sells his half of the bar back to Mick, and leaves town.