The BEST Episodes of Chesapeake Shores
Every episode ever - ranked by fan votes!
Last Updated: Dec 28, 2021
Network: Hallmark Channel
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 - Watercolors, Wishes, and Weddings
Season 4 - Episode 6 - Aired Sep 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.
#2 - Breaking Hearts and Playing Parts
Season 4 - Episode 4 - Aired Sep 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.
#3 - All the Time in the World
Season 4 - Episode 5 - Aired Sep 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.
#4 - Here and There
Season 3 - Episode 6 - Aired Sep 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.
#5 - The End Is Where We Begin
Season 4 - Episode 1 - Aired Aug 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.
#6 - Are the Stars Out Tonight?
Season 5 - Episode 3 - Aired Aug 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.
#7 - Forward to the Past
Season 3 - Episode 9 - Aired Sep 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.
#8 - Forest Through the Trees
Season 2 - Episode 8 - Aired Sep 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.
#9 - Exes Mark the Spot
Season 1 - Episode 9 - Aired Oct 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.
#10 - Happy Trails
Season 5 - Episode 4 - Aired Sep 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.
#11 - They Can't Take That Away From Me
Season 5 - Episode 5 - Aired Sep 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.
#12 - Freefall
Season 2 - Episode 10 - Aired Oct 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.
#13 - The Rock Is Going To Roll
Season 3 - Episode 3 - Aired Aug 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.
#14 - What a Difference a Day Makes
Season 5 - Episode 9 - Aired Oct 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.
#15 - Where or When?
Season 5 - Episode 8 - Aired Oct 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.
#16 - The Royal Court
Season 2 - Episode 9 - Aired Oct 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.
#17 - That Old Feeling
Season 5 - Episode 10 - Aired Oct 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 - Second Chances
Season 1 - Episode 7 - Aired Sep 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.
#19 - An Open Book
Season 3 - Episode 1 - Aired Aug 5, 2018
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.
#20 - Deals Undone
Season 1 - Episode 8 - Aired Oct 2, 2016
As Mick nervously faces a failing business deal, Abby is subpoenaed in the investigation against Wes, and Connor comes up with a plan to prove her innocence. Kevin recovers from his fall at home while struggling to define his future with Georgia, before Jess opens up about a devastating event that could help them understand each other. And Trace learns the warehouse property is still in reach, but his long-held anger toward his own father could prevent him from finally realizing his dream.
#21 - All Our Tomorrows
Season 3 - Episode 8 - Aired Sep 23, 2018
Abby develops an unexpected friendship with a client, while Trace faces conflict at The Bridge. Though initially hesitant to work with her ex-husband’s fiancé, Abby helps her out tremendously and builds a new rapport with her while on a project. Trace, however, has a more difficult time at work and considers putting his friendship with Mick in jeopardy during a professional disagreement. Kevin graduates from his EMT program, but the reality of he and Sarah moving apart looms over the happy occasion. When Connor’s ex-girlfriend offers him a job, he senses familiar romantic feelings developing. At Nell’s urging, Bree shares her manuscript with Megan and begins to realize there are two sides to every story. Meanwhile, Jess receives devastating news about the inn that she fears will impact her whole life – including her future with David.
#22 - A Sonnet for Caroline
Season 4 - Episode 3 - Aired Sep 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.
#23 - Before a Following Sea
Season 3 - Episode 10 - Aired Oct 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.
#24 - Love Is Here to Stay
Season 5 - Episode 6 - Aired Sep 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.
#25 - The Way We Were
Season 3 - Episode 2 - Aired Aug 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.