The WORST episodes of Chesapeake Shores
Every episode of Chesapeake Shores ever, ranked from worst to best by thousands of votes from fans of the show. The worst episodes of Chesapeake Shores!
Abby O'Brien Winters returns from New York to her hometown of Chesapeake Shores, Maryland, after receiving a panicked phone call from her youngest sister Jess, who is renovating the Inn at Eagle Point. Abby's demanding career, divorce, and young daughters have kept her too busy to even think about the town her father built. Saving her sister's inn from foreclosure means dealing not only with her fractured family but also with Trace Riley, her first love whom she abruptly left sixteen years ago. He initially is an obstacle but becomes an unexpected ally and a second chance at finding love. The troubled family dynamic is intensified when Abby's estranged mother comes back to town.
#1 - Where or When?
Season 5 - Episode 8 - Aired 10/3/2021
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.
#2 - The End Is Where We Begin
Season 4 - Episode 1 - Aired 8/25/2019
Trace and Abby's future is uncertain when Trace returns from tour. While they contemplate their relationship, Abby takes on a new client and Trace takes notice of a new musical talent at The Bridge. Kevin plans a special outing with Sarah. Although Jess is happy in her relationship, running the inn David's family bought them is not living up to their expectations. 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.
#3 - Leap of Faith
Season 4 - Episode 2 - Aired 9/1/2019
As Trace searches for his purpose in Chesapeake Shores, a friend tries to persuade 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. Mick is pulled into a former business partner's legal trouble. Jess and David try to return to where it all began. Bree worries that her chemistry with Simon doesn't live up to that of the characters in her autobiographical play. After saving the life of a beloved coach, Kevin contemplates the impact he'd had in his life and the community. Meanwhile, Megan jumps at a new opportunity to help Kevin and Sarah.
#4 - A Sonnet for Caroline
Season 4 - Episode 3 - Aired 9/8/2019
Abby faces career and legal ramifications for blowing the whistle on a Ponzi scheme, and meets an intriguing new man during her leave from work. Trace mentors Emma, a waitress and songwriter, 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, and Nell -- newly back in town -- offers Megan relationship advice. Jess and David navigate a bidding war for a new B&B. Meanwhile, Kevin discovers that his family's good intentions have Sarah feeling overwhelmed; and Connor and Bree contemplate their futures with their respective significant others.
#5 - Breaking Hearts and Playing Parts
Season 4 - Episode 4 - Aired 9/15/2019
Trace comes face to face with the new man in Abby's life when they all work on Caitlyn and Carrie's school play and considers moving on himself. While trying to save his business, Mick falls into old habits of prioritizing work over Megan. Jess and David butt heads on design decisions at the new B&B. When faced with a difficult decision, Connor turns to Nell for relationship advice. As she adapts to 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.
#6 - All the Time in the World
Season 4 - Episode 5 - Aired 9/22/2019
Abby reconsiders her priorities and the future of her career with Jay's support. Trace rebuilds his trust with Emma and offers to buy Mick's share of The Bridge. Despite Abby and Trace's new relationships, each still holds a special place in the other's heart. Jess and David receive guests at the B&B earlier than anticipated. Kevin and Sarah navigate their future including trying to figure out how many children they want. Nell offers advice to 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.
#7 - Watercolors, Wishes, and Weddings
Season 4 - Episode 6 - Aired 9/29/2019
Abby's official first date with Jay gets awkward when they show up to the same restaurant as Trace and Emma. Trace receives an offer to produce an album with Emma but is conflicted about their romantic relationship. A snag in Jess and David's B&B opening threatens to derail David's romantic plans. When planning their future, Kevin and Sarah try to find common ground. With her play opening imminent, Bree is approached by an agent. Both Connor and Abby consider new professional paths. Meanwhile, Mick and Megan try to avoid the relationship mistakes they made the first time around.
#8 - A Kiss is Still a Kiss
Season 5 - Episode 1 - Aired 8/15/2021
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.
#9 - Nice Work If You Can Get It
Season 5 - Episode 2 - Aired 8/22/2021
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.
#10 - Are the Stars Out Tonight?
Season 5 - Episode 3 - Aired 8/29/2021
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.
#11 - What's New?
Season 5 - Episode 7 - Aired 9/26/2021
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.
#12 - Happy Trails
Season 5 - Episode 4 - Aired 9/5/2021
Jess and David host visitors in town for the traditional Snallygaster hunt. Mick and Thomas revisit a weekend-long hiking trip from their youth.
#13 - They Can't Take That Away From Me
Season 5 - Episode 5 - Aired 9/12/2021
As work continues on his hotel, Evan and Abby learn a bit more about each other. Evan stays a night at Jess's B&B.
#14 - Love Is Here to Stay
Season 5 - Episode 6 - Aired 9/19/2021
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.
#15 - Before a Following Sea
Season 3 - Episode 10 - Aired 10/7/2018
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.
#16 - What a Difference a Day Makes
Season 5 - Episode 9 - Aired 10/10/2021
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.
#17 - That Old Feeling
Season 5 - Episode 10 - Aired 10/17/2021
Connor comes to Luke's defense despite personal risks. Abby faces a romantic dilemma when Evan declares his true feelings. Jay wants more than friendship.
#18 - The Best is Yet to Come
Season 6 - Episode 1 - Aired 8/14/2022
The O’Brien family comes together in the aftermath of Connor’s heart attack. Jess and David start to deal with the media fallout after Dennis Peck goes on the run, leaning on one another for support. Abby finally reveals to her family who she called at the end of season five leading to an unexpected yet exciting first date. Mandrake and Kevin talk about their difficult past.
#19 - Memories Are Made of This
Season 6 - Episode 2 - Aired 8/21/2022
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.
#20 - Night and Day
Season 6 - Episode 3 - Aired 8/28/2022
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.
#21 - That's All There Is to That
Season 6 - Episode 4 - Aired 9/4/2022
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.
#22 - L-O-V-E
Season 6 - Episode 5 - Aired 9/11/2022
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.
#23 - Straighten Up and Fly Right
Season 6 - Episode 6 - Aired 9/18/2022
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.
#24 - It’s Not For Me to Say
Season 6 - Episode 7 - Aired 9/25/2022
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.
#25 - I Get a Kick Out of You
Season 6 - Episode 8 - Aired 10/2/2022
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.