Abby O'Brien, a high-powered career woman, divorcee, and mother to twin daughters, takes a trip from New York City to her hometown of Chesapeake Shores when she receives a panicked phone call from her younger sister Jess, who has renovated the charming Inn at Eagle Point. Her visit home brings Abby face to face with her past, including her high school sweetheart Trace, her undemonstrative father Mick who built the town, her daring sister Jess, and her beloved grandmother Nell. This trip also makes Abby notice the toll her career has taken on her ability to be a hands-on mother to her daughters.

Abby thinks about leaving Wall Street; Trace struggles with his past; a confrontation.

As the O'Brien family reunion weekend continues, it seems the family is peacefully cohabiting. but is it just the calm before the inevitable storm ? After Abby announces she's making a permanent move to Chesapeake Shores to raise her daughters, she contends with Connor's harsh judgment as she prepares to go to court to fight for custody. As Abby and Trace agree to put any romantic feelings on hold, Trace struggles with upsetting news from his past. And when Mick offers Bree a way to overcome her writer's block, she finds she'll be making some big life changes of her own.

As Abby settles in at her firm's Baltimore office, she wonders if she can remain just friends with Trace; a beautiful woman from Trace's past arrives unannounced to Chesapeake Shores; Megan tries to repair her relationship with Connor in New York.

As Kevin remains missing, Mick, Nell and the rest of the O'Brien family nervously wait for more news, while Abby goes to New York to fight for custody of her daughters. Despite Leigh's stubborn efforts, Trace continues to hide from his past, but a surprising new idea may have him returning to his music dream after all - if he can make a deal with his ex. And as the family gets the news they've been hoping for, Abby's court ruling will prove this family belongs together more than ever before.

The O'Brien family is stunned when Kevin's fiancee, Georgia, arrives in Chesapeake Shores, determined to take over as he returns home to recover. As Megan immediately clashes with Georgia's overbearing presence, Abby is questioned in connection with a mysterious fraud investigation. And when Trace's own father refuses to help him with a loan, he learns of a bigger betrayal as the warehouse property is sold to an unexpected new investor.

Abby finds out the truth about the fraud investigation from an unlikely source, and suddenly realizes what it could mean to lose it all. As she turns to Trace, he'll confess to the life-changing reason he left his music career in Nashville. And as Megan confronts Mick about the mistakes that once pushed her away, Nell makes an announcement that will stun everyone, just as a horrible accident threatens to reverse all the progress they've made.

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.

As the town's annual lantern festival nears, Trace and each of the O'Briens attempt to put their own challenges aside so four generations of O'Briens can come together for the lantern festival.

When planning her cousin's wedding goes awry, Jess turns to an unexpected source-her mother, Megan-for help. An O'Brien family wedding has some unexpected tension when Mick is confronted by an adversary from his past.

School's back in session in "Chesapeake Shores," but a fresh start for some brings back old memories for others in "Photographs and Memories". As Abby sends her girls off to their first day at a new school, conflict arises between Trace and Wes about their roles in the family - complicated further by a Nashville recording label taking interest in Trace's new demo with a former flame. The O'Brien siblings reminisce over their own school days watching home movies shot by Megan, but these movies leave Jess feeling left out and angry at her mother for leaving when she was young. Nell helps Connor dress professionally for his new career - and adulthood - but struggles to prevent Mick from butting heads with his brother Thomas over family land. Like the rest of the family, Bree and Kevin attempt to bid farewell to their pasts to make way for future opportunities.

Nashville is calling Trace, but leaving town creates a difficult distance between he and Abby. Trace hits the road to record an album with his ex-girlfriend Leigh, but has trouble channeling creative inspiration while he is away from Abby. A well-intentioned Jess creates trouble for Bree when she advertises that a famous author will attend a book reading at Bree's new bookstore. Ready to move on from his past relationship, Kevin tries to impress a free spirited firefighter on their first date. As Mick continues his plans to develop family land, Nell attempts to have him reconcile with his brother, Thomas.

In "Buried Treasures," the O'Briens dig up the past - both literally and figuratively - on "Chesapeake Shores." 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. While Trace is in Nashville fighting his producer Mark Hall to keep Leigh on an upcoming album at the risk of his own career, Abby meets a handsome widower in the PTA. At her bed and breakfast, Jess deals with a high maintenance customer, but gets more than she bargains for when his true identity is revealed. Mick and Thomas continue to spar over a family land development deal, never seeing eye-to-eye about the past or the future. Megan reconnects with the family by giving Connor dating advice and tutoring her granddaughters.

Chesapeake Shores is filled with music as the town awaits the grand opening of The Bridge nightclub in "Grand Openings". As the nightclub opening nears, Trace spends late nights practicing with Leigh and his band, while 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. Frustrated with her own work prospects, Megan (Barbara Niven) receives an endorsement from an unexpected ally. Jess begins to develop feelings for someone at work, while Bree is surprised at her bookstore by a new admirer - and famous author. Connor reconnects with former flame Danielle, and Kevin has eyes for a free-spirited firefighter. Sensing romance in the air, Nell hosts a dinner for her grandchildren and their new love interests.

In "Chesapeake Shores," each member of the O'Brien family is influenced by the past as they plan their futures in "All Our Yesterdays." 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. Just like Jess, Bree is afraid to move forward with her new admirer. Connor and Kevin both contemplate their careers, concerned they may be headed down the wrong paths. Overloaded with work, both Trace and Abby try to find time to spend with one another and their families. On advice from Nell, Megan tells her children the real reason she left for New York all those years ago.

Hoping to resolve some personal conflicts brewing in "Chesapeake Shores," the O'Briens face crucial issues head on in "Forest Through the Trees." Away from the distraction of technology, Abby and Trace talk about their past and the future during a camping getaway. With some encouragement from Nell, Mick and Thomas try to work out their differences in person. Bree has trouble resisting the charms of her new suitor that Megan invited to town, and spends some time getting to know him. After a recent kiss, Jess grapples with her feelings toward David, afraid that pursuing romance will ruin their friendship. Kevin also faces uncertainty about his new romance when a loss from her past brings up difficult memories from his own. A newly unemployed Connor receives a work offer from a surprising source.

A viral video and a birthday have two residents of "Chesapeake Shores" receiving special treatment in "The Royal Court." After his band's music 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. Kevin finds inspiration to follow his passion on a trip to visit one of his fallen army friends' mothers with Bree. Watching the shop in Bree's absence, Jess discovers that running a bookstore is not as easy as she thought. Connor turns to Danielle when he finds his career direction shifting. After Mick refuses to use incriminating information against his brother Thomas, he must find a new investor for his development deal.

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.

Trace returns to Abby after three months on tour, only to discover a family in turmoil. Bree's completed manuscript turns out to be a thinly veiled story of the family. Mick ends the fight over the family trust but begins a feud with Connor.

Nell tries to save the Wish Fountain. Abby discovers a never-opened letter that she sent to Trace. Mick inherits a sailboat and reunites with his brother Thomas. Bree welcomes an old friend back into her life.

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, as does Mick and Megan, who begin to suspect that old feelings never go away. Meanwhile, Sarah is injured on the job, and Kevin has to take a step back into his own past to help Sarah move forward.

Wes's new girlfriend reminds Abby that she might not be the only "mom" in Carrie and Caitlyn's life, and David and Simon's presence in Chesapeake Shores puts Jess and Bree in an unusual position.

Trace discovers that the general manager of The Bridge stole large sums of money. Abby realizes that she can't be a perfect boss, parent and girlfriend. David Peck's sister arrives, threatening Jess and David's relationship.

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, and it appears that the same might be true with the O'Brien family.

Chaos reigns with the closure of The Bridge, the O'Briens are at war over Bree's manuscript, Kevin is heartbroken visiting Sarah's family in Philadelphia, and Trace realizes that he might not return to Chesapeake Shores.

Abby finally has to make a decision whether or not to break up with Trace for good. Bree's relationship with Simon is rocked when Caroline appears, and David and Jess have to finally figure out their relationship without the B and B.

After following his dreams to go on tour, Trace returns to an uncertain future with Abby. Kevin plans a special outing with Sarah. Though happy with her own relationship with David, running his family's inn together does not meet Jess's expectations. Fresh off penning a national bestseller, Bree meets with potential producers for a new play. Meanwhile, Mick discovers one of his contractors has engaged in suspicious business practices, and Connor questions his career path.

Trace's commitment to planting roots and winning Abby back is tested when a friend urges him to return to his music career. Abby puts her work life in jeopardy investigating a client's dubious business practices, and Connor also faces professional consequences after making an impulsive decision. Jess and David try to go back to where it all started. Bree worries that her chemistry with Simon does not live up to that of her autobiographical play's characters.

The consequences of blowing the whistle on a Ponzi scheme begin to hit Abby so she tries to distract herself by volunteering during her leave from work where she meets an intriguing new man. Trace mentors Emma and encourages her to perform her music at The Bridge. Mick and Megan fear that the return of their romantic feelings will complicate their friendship. Fortunately, Nell is back in town as a confidant for Megan. Jess and David navigate a bidding war for a new B&B.

While helping out on Cailtyn and Carrie's school play, Trace meets the new man in Abby's life and considers moving on himself. While trying to save his business, Mick falls into old habits of prioritizing work over Megan. In the wake of a big change in her personal life, Bree struggles to rewrite the ending of her play. Meanwhile, Kevin and Sarah share a big announcement with the O'Briens, which they receive with less enthusiasm than expected.

After a stressful deposition, Abby reconsiders her priorities and the future of her career with Jay's support. Trace 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. Kevin and Sarah struggle to see eye to eye about what their future together holds. Meanwhile, Bree prepares for the premiere of her play, and Connor pursues a new job.

Abby's official first date with Jay gets awkward when they show up to the same restaurant as Trace and Emma, revealing lingering chemistry between the former couple and causing Trace to reconsider recording a duet album with Emma. Meanwhile, family drama bubbles beneath the surface of O'Brien family celebrations. Standing at personal and professional crossroads, Trace and the O'Briens all have important decisions to make.

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.

Wanting to reconnect with each other, Mick and Thomas set out on a two-day hike on the Appalachian Trail like they did when they were younger. Abby and Connor make an important discovery that could help exonerate their dad in the Dilpher case. Kevin becomes concerned about fire department Captain Gahagan when he notices his memory lapses. Meanwhile, the B&B is filled with guests in town for the annual Snally Hunting weekend, in search of the mythical yet infamous creature, the Snallygaster.

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 Luke's 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. When 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; everyone finally discovers 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, while Abby becomes comfortable with her new romance.

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. Sarah and Kevin's baby arrives, starting a week of celebration bringing the O'Briens together one last time in Chesapeake Shores.

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, while Abby becomes comfortable with her new romance.

Wanting to reconnect with each other, Mick and Thomas set out on a two-day hike on the Appalachian Trail like they did when they were younger. Abby and Connor make an important discovery that could help exonerate their dad in the Dilpher case. Kevin becomes concerned about fire department Captain Gahagan when he notices his memory lapses. Meanwhile, the B&B is filled with guests in town for the annual Snally Hunting weekend, in search of the mythical yet infamous creature, the Snallygaster.

As the town's annual lantern festival nears, Trace and each of the O'Briens attempt to put their own challenges aside so four generations of O'Briens can come together for the lantern festival.

Evan finds himself wondering if he has feelings for Abby. When Luke is threatened with going back to prison, Connor sacrifices to help Luke and Bree.

Kevin and Sarah try to keep a secret while Bree discovers one from Luke's past. Evan whisks Abby away on a business trip, but his intentions are not what she originally thinks.

As the O'Brien family reunion weekend continues, it seems the family is peacefully cohabiting. but is it just the calm before the inevitable storm ? After Abby announces she's making a permanent move to Chesapeake Shores to raise her daughters, she contends with Connor's harsh judgment as she prepares to go to court to fight for custody. As Abby and Trace agree to put any romantic feelings on hold, Trace struggles with upsetting news from his past. And when Mick offers Bree a way to overcome her writer's block, she finds she'll be making some big life changes of her own.

As Abby settles in at her firm's Baltimore office, she wonders if she can remain just friends with Trace; a beautiful woman from Trace's past arrives unannounced to Chesapeake Shores; Megan tries to repair her relationship with Connor in New York.

As Kevin remains missing, Mick, Nell and the rest of the O'Brien family nervously wait for more news, while Abby goes to New York to fight for custody of her daughters. Despite Leigh's stubborn efforts, Trace continues to hide from his past, but a surprising new idea may have him returning to his music dream after all - if he can make a deal with his ex. And as the family gets the news they've been hoping for, Abby's court ruling will prove this family belongs together more than ever before.

Abby thinks about leaving Wall Street; Trace struggles with his past; a confrontation.