The BEST episodes of Chesapeake Shores
Every episode of Chesapeake Shores ever, ranked from best to worst by thousands of votes from fans of the show. The best 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 - All or Nothing at All
Season 6 - Episode 10 - Aired 10/16/2022
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.
#2 - 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.
#3 - 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.
#4 - 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.
#5 - Spring Can Really Hang You Up the Most
Season 6 - Episode 9 - Aired 10/9/2022
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.
#6 - 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.
#7 - Here and There
Season 3 - Episode 6 - Aired 9/9/2018
Abby learns her ex-husband is in a serious relationship navigates their new family dynamic. Abby misses Trace by her side as she explores the new co-parenting roles with Wes and his girlfriend. Pulled in many directions with work obligations, Trace misses out on family moments with Abby and the girls. Mick and Megan’s relationship continues to evolve, but is influenced by their past. Having worked independently for months, Jess adjusts to David’s return to the bed and breakfast. Also adjusting to a man in her life is Bree, who attempts to define her partially professional, partially romantic relationship with Simon. At the Chesapeake Shores Fire Department, Kevin enjoys a week of on-the-job training with Sarah. Meanwhile, Nell recruits Connor to investigate a contestant who is breaking the rules in an annual gardening competition, but a surprising discovery makes her rethink the plan.
#8 - 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.
#9 - 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.
#10 - Forest Through the Trees
Season 2 - Episode 8 - Aired 9/24/2017
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.
#11 - Exes Mark the Spot
Season 1 - Episode 9 - Aired 10/9/2016
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.
#12 - 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.
#13 - 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.
#14 - 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.
#15 - Freefall
Season 2 - Episode 10 - Aired 10/8/2017
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.
#16 - The Rock Is Going To Roll
Season 3 - Episode 3 - Aired 8/19/2018
Trace and Abby hit an unexpected hiccup in their family dynamic after Trace takes on more of a father figure role. While Trace reading bedtime stories to the girls is a milestone in his relationship with Abby, the moment has an unexpected consequence when the girls question his role in their lives. Bree joins Jess on a trip to visit David and his parents, but Jess continues to harbor hurt feelings over Bree’s manuscript. Jess needs Bree’s support more than ever, though, when she discovers the real reason David’s parents want to meet her. Mick sees striking similarities between his troubled relationship with his brother and his sons’ relationship with one another when Kevin and Connor feud over Kevin’s meddling in Connor’s relationship. Meanwhile, Nell ramps up her persuasive tactics to convince the mayor to keep the wish fountain.
#17 - Forward to the Past
Season 3 - Episode 9 - Aired 9/30/2018
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.
#18 - The Royal Court
Season 2 - Episode 9 - Aired 10/1/2017
Trace receives offers from music executives after his band's video goes viral, but he tries to convince his band to give Mark Hall another shot. Meanwhile, Abby, Nell and Megan spend some family time together preparing a princess party for Carrie.
#19 - 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.
#20 - 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.
#21 - 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.
#22 - The Way We Were
Season 3 - Episode 2 - Aired 8/12/2018
Though they are blissfully together in Chesapeake Shores, Trace faces a difficult decision and Abby is confronted by ghosts from her past. When a country legend offers Trace a gig that could propel his career, he weighs the benefits against the massive cost of being away from Abby and the girls again. Abby feels guilty when she finds a letter that she wrote Trace years ago – still unopened – and questions what to do with it. Mick and Megan meet up with Thomas, whose rekindled marriage with his once-estranged wife prompts each of them to assess their own relationship. Bree is surprised when Simon returns to her life, but is without her go to sounding board because Jess is still hurt about her manuscript. Kevin is concerned when he sees Connor’s girlfriend out with another man. Meanwhile, Nell continues her fight to preserve the town’s wishing fountain.
#23 - 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.
#24 - Second Chances
Season 1 - Episode 7 - Aired 9/25/2016
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.
#25 - Love Eventually
Season 3 - Episode 5 - Aired 9/2/2018
Abby is burdened by continued paparazzi attention from Trace’s growing fame. As he works through his loneliness while on tour away from Abby, Trace writes a song for Abby, which prompts an unexpected reaction from Leigh. Mick tries to repair his relationship with Connor at Megan’s insistence, but their tumultuous history makes Connor reluctant to reconcile. Kevin is concerned when Sarah seeks adventure after a near-death accident at work, noticing similarities between her behavior and his after his wartime injury. Bree edits her novel with Simon’s help, and realizes she and one of her characters share the same drive for self-preservation that stunts their relationships. Meanwhile, Jess fears her relationship with David is over.
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