The BEST episodes of Chesapeake Shores season 5

Every episode of Chesapeake Shores season 5, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Chesapeake Shores season 5!

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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They Can't Take That Away From Me
star
7.88
66 votes

#1 - 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.

Directors: Terry Ingram
Watch Now:AmazonApple TV
Where or When?
star
7.84
74 votes

#2 - 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.

Directors: Siobhan Devine
Watch Now:AmazonApple TV
What a Difference a Day Makes
star
7.84
67 votes

#3 - 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.

Directors: Terry Ingram
Writer: Phoef Sutton
Watch Now:AmazonApple TV
That Old Feeling
star
7.80
65 votes

#4 - 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.

Directors: Terry Ingram
Writer: Phoef Sutton
Watch Now:AmazonApple TV
A Kiss is Still a Kiss
star
7.75
75 votes

#5 - A Kiss is Still a Kiss

Season 5 - Episode 1 - Aired 8/15/2021

As the O'Brien family welcomes Bree home from London they ruminate on how the past two months have changed them all. Kevin and Sarah try for a baby, Jess and David plan for their wedding, and Abby thinks back to her conversation with Trace after their kiss on the beach.

Directors: Michael Robison
Writer: Phoef Sutton
Watch Now:AmazonApple TV
Are the Stars Out Tonight?
star
7.72
76 votes

#6 - Are the Stars Out Tonight?

Season 5 - Episode 3 - Aired 8/29/2021

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.

Watch Now:AmazonApple TV
Love Is Here to Stay
star
7.72
65 votes

#7 - Love Is Here to Stay

Season 5 - Episode 6 - Aired 9/19/2021

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.

Directors: Terry Ingram
Watch Now:AmazonApple TV
What's New?
star
7.69
65 votes

#8 - What's New?

Season 5 - Episode 7 - Aired 9/26/2021

When Evan comes to the house, he throws out his back and must recover for a few days on the O'Brien couch, connecting him with the family in a way Abby never anticipated.

Directors: Siobhan Devine
Writer: Phoef Sutton
Watch Now:AmazonApple TV
Happy Trails
star
7.65
69 votes

#9 - Happy Trails

Season 5 - Episode 4 - Aired 9/5/2021

Jess and David host visitors in town for the traditional Snallygaster hunt. Mick and Thomas revisit a weekend-long hiking trip from their youth.

Watch Now:AmazonApple TV
Nice Work If You Can Get It
star
7.63
71 votes

#10 - Nice Work If You Can Get It

Season 5 - Episode 2 - Aired 8/22/2021

Abby reflects on the past and contemplates a future on her own terms. She and Mick deal with the damage to the reputation of O'Brien Construction, Jess struggles with something David's parents gave her, and Bree realizes two different men from her past may be returning to her life and her heart.

Directors: Michael Robison
Watch Now:AmazonApple TV