The BEST episodes of Chesapeake Shores season 4

Every episode of Chesapeake Shores season 4, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Chesapeake Shores season 4!

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.

Last Updated: 3/24/2024Network: Hallmark ChannelStatus: Ended
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Watercolors, Wishes, and Weddings
star
8.02
99 votes

#1 - 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.

Directors: Terry Ingram
Watch Now:AmazonApple TV
Breaking Hearts and Playing Parts
star
7.98
91 votes

#2 - 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.

Directors: Andy Mikita
Watch Now:AmazonApple TV
All the Time in the World
star
7.93
89 votes

#3 - 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.

Directors: Terry Ingram
Watch Now:AmazonApple TV
The End Is Where We Begin
star
7.92
103 votes

#4 - 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.

Directors: Terry Ingram
Watch Now:AmazonApple TV
A Sonnet for Caroline
star
7.71
99 votes

#5 - 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.

Directors: Andy Mikita
Watch Now:AmazonApple TV
Leap of Faith
star
7.62
104 votes

#6 - 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.

Directors: Terry Ingram
Watch Now:AmazonApple TV