Chesapeake Shores

10 Best Episodes of Chesapeake Shores

A divorced mom deals with an old romance and complicated family issues when she returns to her hometown with her twin daughters.

Written by Sophie and last updated on jan 04, 2023.

PS: The following content contains spoilers!

PPS: I will admit that parts of this page was written with the help of AI - it makes my work so much easier to not start from a blank page!

Chesapeake Shores - S6E1

#15 - The Best is Yet to Come (Season 6 - Episode 1)

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, and we finally discover who Abby called.

The episode was rated 7.94 from 52 votes.

Chesapeake Shores - S5E8

#14 - Where or When? (Season 5 - Episode 8)


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.

The episode was rated 7.95 from 55 votes.

Chesapeake Shores - S3E3

#13 - The Rock is Going to Roll (Season 3 - Episode 3)

While Jess and Bree in Maine visit David and his fabulously wealthy family, Trace's role in Abby's family is questioned. Meanwhile, everyone helps out running the B&B and Wordplay, and Connor learns the truth about Danielle.

The episode was rated 7.95 from 102 votes.

Chesapeake Shores - S1E9

#12 - Exes Mark the Spot (Season 1 - Episode 9)


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.

The episode was rated 7.97 from 331 votes.

Chesapeake Shores - S6E4

#11 - That's All There Is to That (Season 6 - Episode 4)

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.

The episode was rated 7.97 from 33 votes.

Chesapeake Shores - S2E10

#10 - Freefall (Season 2 - Episode 10)


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 in the present.

The episode was rated 7.98 from 204 votes.

Chesapeake Shores - S4E1

#9 - The End Is Where We Begin (Season 4 - Episode 1)

Kevin mulls marriage with Sarah; Jess and David run their new B&B in Tanglewood; and Abby and Mick both discover that their careers are in jeopardy.

The episode was rated 8.00 from 99 votes.

Chesapeake Shores - S3E9

#8 - Forward to the Past (Season 3 - Episode 9)


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.

The episode was rated 8.00 from 104 votes.

Chesapeake Shores - S2E8

#7 - Forest Through the Trees (Season 2 - Episode 8)

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.

The episode was rated 8.01 from 227 votes.

Chesapeake Shores - S5E5

#6 - They Can't Take That Away From Me (Season 5 - Episode 5)


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.

The episode was rated 8.04 from 50 votes.

Chesapeake Shores - S3E6

#5 - Here and There (Season 3 - Episode 6)

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.

The episode was rated 8.04 from 98 votes.

Chesapeake Shores - S4E5

#4 - All the time in the World (Season 4 - Episode 5)


Trace rethinks sharing ownership of The Bridge with Mick. Jay helps Abby reconsider her priorities. Jess and David find themselves hosting guests before they are ready. Connor pursues an intriguing new opportunity. Kevin and Sarah discuss their future. Bree prepares for opening day of her play.

The episode was rated 8.06 from 80 votes.

Chesapeake Shores - S4E4

#3 - Breaking Hearts and Playing Parts (Season 4 - Episode 4)

The play is in jeopardy, it's Abby and Trace to rescue. David and Jess learn to work together, Bree learns to work alone. Mick and Megan come together while Connor goes it alone. Kevin and Sara return with a surprise announcement.

The episode was rated 8.08 from 83 votes.

Chesapeake Shores - S4E6

#2 - Watercolors, Wishes, and Weddings (Season 4 - Episode 6)


As season four comes to a close, Trace and the O’Briens face decisions affecting their personal and professional lives. Trace weighs his relationship with Emma against her musical potential. Abby and Connor consider new career paths, while a new agent has Bree questioning what’s next.

The episode was rated 8.10 from 90 votes.

Chesapeake Shores - S6E6

#1 - Straighten Up and Fly Right (Season 6 - Episode 6)

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.

The episode was rated 8.18 from 28 votes.

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