The BEST Episodes of Chesapeake Shores

Every episode ever - ranked by fan votes!

Last Updated: Jan 18, 2021

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.

Watercolors, Wishes, and Weddings

#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.

star 8.36
61 votes
Directors: Terry Ingram
Writers: Michael Berns
All the Time in the World

#2 - 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.

star 8.19
57 votes
Directors: Terry Ingram
Writers: Kirsten Hansen, Michael Berns
 Breaking Hearts and Playing Parts

#3 - 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.

star 8.19
58 votes
Directors: Andy Mikita
Writers: Michael Berns
The End Is Where We Begin

#4 - 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.

star 8.07
74 votes
Directors: Terry Ingram
Writers: Michael Berns
Forward to the Past

#5 - 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.

star 8.04
85 votes
Directors: Mike Rohl
Writers: Kristen Hansen, Michael Berns
Here and There

#6 - 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.

star 8.02
83 votes
Directors: Sean McNamara
Writers: Brian Ross
Exes Mark the Spot

#7 - 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.

star 8.00
349 votes
Directors: Martin Wood
Writers: Nancey Silvers
Forest Through the Trees

#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.

star 7.99
240 votes
Directors: Anne Wheeler
Writers: Ann Lewis Hamilton
A Sonnet for Caroline

#9 - 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.

star 7.98
64 votes
Directors: Andy Mikita
Writers: Nancey Silvers

#10 - 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.

star 7.94
214 votes
Directors: Andy Mikita
Writers: Ann Lewis Hamilton
The Rock Is Going To Roll

#11 - 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.

star 7.94
86 votes
Directors: Terry Ingram
Writers: Brian L. Ross
The Royal Court

#12 - 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.

star 7.89
210 votes
Directors: Andy Mikita
Writers: Nancey Silvers
Second Chances

#13 - 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.

star 7.88
355 votes
Directors: Anne Wheeler
Writers: Kirsten Hansen
Deals Undone

#14 - 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.

star 7.87
358 votes
Directors: Martin Wood
Writers: Nancey Silvers
All Our Tomorrows

#15 - 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.

star 7.87
83 votes
Directors: Terry Ingram
Writers: Kristen Hansen
Before a Following Sea

#16 - 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.

star 7.86
79 votes
Directors: Mike Rohl
Writers: Michael Berns
An Open Book

#17 - 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.

star 7.85
102 votes
Directors: Sean McNamara
Writers: Michael Berns
Georgia on My Mind

#18 - Georgia on My Mind

Season 1 - Episode 6 - Aired Sep 18, 2016

Kevin's fiancée arrives in town, surprising the O'Briens; Abby gets tangled in a fraud investigations; Trace receives bad news about the water-house property he covets.

star 7.84
348 votes
Directors: Anne Wheeler
Writers: John Tinker
Buried Treasures

#19 - Buried Treasures

Season 2 - Episode 5 - Aired Sep 3, 2017

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.

star 7.84
263 votes
Directors: Mike Rohl
Writers: Michael MacLennan
Home to Roost (1)

#20 - Home to Roost (1)

Season 1 - Episode 2 - Aired Aug 21, 2016

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.

star 7.84
412 votes
We're Gaining a Daughter

#21 - We're Gaining a Daughter

Season 1 - Episode 5 - Aired Sep 11, 2016

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.

star 7.83
345 votes
Directors: Martin Wood
Writers: Nancey Silvers
Secrets, Lies and School Supplies

#22 - Secrets, Lies and School Supplies

Season 2 - Episode 1 - Aired Aug 6, 2017

As Abby and the rest of the O’Briens prepare for the town’s annual lantern festival, Trace must return to Nashville to face a mistake from his past. Mick takes his granddaughters back-to-school shopping while covertly working on a business deal that is bound to cause family conflict.

star 7.83
344 votes
Directors: Sean McNamara
Writers: Nancey Silvers
The Way We Were

#23 - 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.

star 7.82
95 votes
Directors: Sean McNamara
Writers: Nancey Silvers
We're Not Losing a Son...

#24 - We're Not Losing a Son...

Season 1 - Episode 4 - Aired Sep 4, 2016

As Abby settles in and starts her job at her firm's Baltimore office, she wonders if she can remain just friends with Trace.

star 7.81
370 votes
Directors: Martin Wood
Writers: Nancey Silvers
 Leap of Faith

#25 - Leap of Faith

Season 4 - Episode 2 - Aired Sep 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.

star 7.81
68 votes
Directors: Terry Ingram
Writers: Kirsten Hansen