A divorced mom deals with an old romance and complicated family issues when she returns to her hometown with her twin daughters.
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 has renovated the charming Inn at Eagle Point. Saving the inn from foreclosure means dealing not only with her fractured family but also with the man she left ten years ago.
Abby considers leaving her Wall Street job and has an unforeseen showdown with her ex. Meanwhile, Trace has trouble explaining why he left Nashville; and Jess wants to open a new business on her own.
As the O'Brien family reunion weekend continues, it seems the family is peacefully cohabitating - but is it just the calm before the inevitable storm?
As Abby settles in and starts her job at her firm's Baltimore office, she wonders if she can remain just friends with Trace.
As Kevin remains missing, Mick, Nell and the rest of the O'Brien family nervously wait for more news; Abby goes to New York to fight for custody of her daughters; Trace continues to hide from his past, but a surprising new idea may have him returning to his music dream after all.
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.
Trace makes a confession regarding why he left Nashville. Meanwhile, Megan confronts Mick about past mistakes responsible for pushing her away; and Abby learns the truth about the fraud investigation from a surprising source.
Mick nervously faces a failing business deal; Abby is subpoenaed in the investigation against Wes; Kevin recovers from his fall at home while struggling to define his future with Georgia; Trace learns the warehouse property is still in reach.
Abby and Trace seem finally ready to move forward; Jess, David and Bree attempt to untangle their complicated love triangle; an emergency phone call puts Trace in trouble with the law.
Abby bails out Trace, who goes to his ailing father in the hospital; Abby balances work and mom life, worried about introducing Trace to her girls; Mick looks into developing the O'Brien Trust and the complications that will follow.
Trace discovers Mick plans to sell the club, putting them at odds; Abby ends up between Trace and Mick when it comes to the club's fate, and the O'Brien Trust files overwhelm her at work; Megan moves into her new home.
Trace and Leigh finish their last song for the demo and send it to the record company; Abby discusses her possible future with Trace and they share a romantic moment; Mick goes head to head with estranged brother Thomas about the trust.
Trace makes his final preparations for the club opening prior to leaving for Nashville; Trace and Leigh meet the music producer who wants to produce their songs; Abby meets with Thomas to hear his side of the story about the O'Brien Trust.
Nell discovers a treasure map that Bree made as a teen, leading Bree and Kevin to hunt for a family time capsule in the backyard; Trace is in Nashville fighting his producer to keep Leigh on an upcoming album at the risk of his own career.
As the nightclub opening nears, Trace spends late nights practicing with Leigh and his band; Mick fights city hall to receive a live music permit; Abby receives a promotion at work, but it leaves her with less time to spend with the family and Trace.
Mick receives damaging information about Thomas, and considers whether to use it in their town hall debate; Jess plans a special meal to win David over; Bree fears moving forward with her new admirer.
Away from the distraction of technology, Abby and Trace talk about their past and the future during a camping getaway; Nell, Mick and Thomas try to work out their differences in person; Bree has trouble resisting the charms of her new suitor.
After his band's video goes viral, Trace receives offers from music executives, but tries to convince his band to give Mark Hall another shot; Abby, Nell and Megan spend some family time together preparing a princess birthday party for Carrie.
After Mark offers Trace and his band a worldwide tour deal, Trace and Abby worry about how it might impact their future together. As Nell ponders a lost love from her past, Abby, Jess and Bree are faced with the possibility of losing their new loves in the present.
After months away on tour, Trace returns to Abby. Trace's Chesapeake Shores homecoming becomes complicated, however, when his growing fame draws unwanted media attention to his relationship with Abby and her girls. Mick faces off against Connor in an environmental legal battle. Though the two are on opposing sides, Mick tries to warn his son about a major error before it is too late. Jess discovers Bree's manuscript and is shocked to discover what's inside. Meanwhile, Kevin continues his paramedic training, and grows closer with Sarah. When Trace and the O'Brien family come together for the annual oyster festival, Nell recruits the family to save a beloved landmark.
After Trace's dad cleans out the attic at home, Trace and Abby goes through his old things. While doing so, Abby finds an old unopened letter she wrote years ago. Mick begins working on refinishing an old boat. Conner and Kevin's relationship gets strained when Kevin discovers Danielle in a lie. Bree asks Abby to read her manuscript, hoping to prove a point that it isn't about Jess. Bree gets an opportunity to produce a play in Baltimore, where she runs into her old flame, Simon. Thomas and his wife Robin arrive in town, much to the displeasure of Nell, who is working to save the town's beloved fountain.
Trace's role in Abby's family is questioned; everyone helps out running the B&B; Connor learns the truth about Danielle.
Jess and Bree discover David's parents' secret plans; Abby joins Trace on tour; Thomas's vow renewal sparks Mick and Megan to re-examine their own relationship; Connor reconciles with Kevin.
With Trace still on the road, Abby and Trace find a way to combat the loneliness; with Simon in town, Bree has to define a new normal; Sarah is injured on the job.
Boyfriend and girlfriend problems abound: While Wes's new practically perfect girlfriend reminds Abby that she might be the only "mom" in Carrie and Caitlyn's life; David and Simon's presence in Chesapeake Shores puts Jess and Bree in an unusual position; and Mick and Megan finally come to terms with the direction of their relationship. Meanwhile, Nell enlists Connor's help when she discovers that her rival in a flower show is cheating.
Trace discovers that the general manager of The Bridge stole large sums of money, pitting Trace and Mick against one another. At the same time, Abby realizes that she can't be a perfect boss, parent and girlfriend, and David Peck's sister arrives, threatening Jess and David's relationship. Meanwhile, Connor rediscovers Danielle, and Kevin accepts that he might lose Sarah.
Battle lines form after Megan reads Bree's manuscript; Trace and Mick disagree over the future of the Bridge; with Jess's B&B's being devoured from within, it appears that the same might be true with the O'Brien family.
Chaos reigns with the closure of the Bridge, and the O'Briens are at war over Bree's manuscript. Meanwhile, Kevin is heartbroken visiting Sarah's family in Philadelphia, especially after he's offered his dream job back in Chesapeake Shores. When Trace realizes that he might not return to Chesapeake Shores, his relationship with Abby is cast into doubt, as Jess wonders if her relationship with David can survive without the B&B.
On the eve of the Chesapeake Shores Regatta, with Mick recruiting family members to join him on the water, Abby finally has to make a decision whether or not to break up with Trace for good. Meanwhile, Bree's relationship with Simon is rocked when Caroline appears, and David and Jess have to finally figure out their relationship without the B&B.In a surprise twist, a letter from Ireland might decide Nell's future.
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.
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; and Bree and Connor suspect true love might not last forever.
The play is 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.
Trace and Abby enjoy new relationships in "Chesapeake Shores," but are not sure that they've found in their partners what they once had with each other. After a stressful deposition, Abby reconsiders her priorities and the future of her career with Jay's support. Trace rebuilds his trust with Emma and reaffirms his commitment to Chesapeake Shores when he offers to buy Mick's share of The Bridge. Jess and David receive guests at the B&B earlier than anticipated but rally together to get through it. Kevin and Sarah struggle to see eye to eye about what their future together holds. Nell offers advice to both Mick and Megan when they encounter issues in their newly rekindled relationship. Meanwhile, Bree prepares for the premiere of her play, and Connor pursues a new job.
Mick and Megan celebrate their old life, Kevin and Sarah cherish their new one, Jess and David await the start of theirs. With Connor and Bree's careers in flux, Trace and Abby confront their future… and their future together.
As the O'Brien family welcomes Bree home from London they ruminate on how the past two months have changed them all. Kevin and Sarah try for a baby, Jess and David plan for their wedding, and Abby thinks back to her conversation with Trace after their kiss on the beach.
Abby reflects on the past and contemplates a future on her own terms. She and Mick deal with the damage to the reputation of O'Brien Construction, Jess struggles with something David's parents gave her, and Bree realizes two different men from her past may be returning to her life and her heart.
O'Brien Construction's eccentric billionaire client, Evan Kincaid, comes to town and throws Abby and Mick off their game. At a moment of triumph, Connor discovers his law firm is hiding information from him, and Megan discovers a lost painting that leads her to a famous, reclusive local artist who wants nothing to do with her.
Jess and David host visitors in town for the traditional Snallygaster hunt. Meanwhile, Mick and Thomas revisit a weekend-long hiking trip from their youth.
As work continues on his hotel, Evan and Abby learn a bit more about each other, and Evan stays a night at Jess's B&B.
Jess and David's wedding is here, but the O'Brien family still has a lot to face before the celebration. Abby and Evan get into an argument over his hotel, threatening the entire project.
When Evan comes to the house, he throws out his back and must recover for a few days on the O'Brien couch, connecting him with the family in a way Abby never anticipated.
Kevin and Sarah try to keep a secret while Bree discovers one from Lukes past. Evan whisks Abby away on a business trip, but his intentions are not what she originally thinks.
Evan finds himself wondering if he has feelings for Abby. Luke is threatened with going back to prison. Connor sacrifices to help Luke and Bree.
Connor comes to Luke's defense despite personal risks. Abby faces a romantic dilemma. Jay wants more than friendship.
The O'Brien family comes together in the aftermath of Connor's heart attack. Jess and David deal with media fallout after Dennis Peck goes on the run, and we finally discover who Abby called.
Abby plans a second date with Evan. Deidre and Alexandra Peck visit the B&B to avoid negative media attention, and with Connor recovering, Megan decides whether to work in L.A. or stay to help.
Abby and Evan participate in a scavenger hunt. Mick and Megan have a serious talk about past relationships. Connor breaks out to return to his apartment. Bree helps Luke with night terrors.
Sarah and Kevin come together with exciting news. Connor and Margaret's law firm struggles to make ends meet, and when Mick's pill addiction starts to noticeably affect his life, the O'Briens must rally together and stage an intervention.
A fortune telling machine shares uncomfortable truths with the O'Brien couples. Mick and Megan struggle with their long-distance relationship, Abby's more comfortable with her new romance.
Various issues are troubling the O'Briens. Mick is in denial about his addiction. Margaret passes the bar. Jess pursues a new idea, and Bree tries mending the rift between her and Luke.
Kevin learns something new while David questions what he thought was true. Bree finds she and Luke share a birthday. Kevin discovers the gender of the baby. David confronts his father.
Secrets are exposed to reveal the past can't be escaped. A DNA test reveals a location for Evan's father. Jess hosts a historical reenactment. A Hollywood star comes to offer Bree a movie deal.
Mick gets closer to the ones he loves while Evan and Luke push themselves away. Mick continues to rebuild his relationship with Megan. Luke recovers from a gunshot after stopping a robbery.
Mick and Megan reunite in the thrilling finale. Sarah and Kevin's baby arrives, starting a week of celebration bringing the O'Briens together one last time in Chesapeake Shores.
