Chesapeake Shores Season 5 2021 Cast Premiere Dates Times Where To Watch

Ready for its fifth season, here’s everything we know about the new season of Chesapeake Shores so far.

What’s Chesapeake Shores about?

Chesapeake Shores follows the life and times of the O’Brien family and focuses on Abby O’Brien (Meghan Ory). After her divorce, Abby moves back home to Chesapeake Shores with her two children and rekindles a romance with her high school sweetheart, Trace Riley (Jesse Metcalfe). But we’re expecting that the change in season 5 as actor Jesse Metcalfe will be leaving early in the season.

When will season 5 of Chesapeake Shores premiere?

Chesapeake Shores will come back for season 5 at 8 p.m. ET on August 15 on Hallmark Channel.

Is Chesapeake Shores based on a book?

Yes. Chesapeake Shores is based on a series of books by Sheryl Woods.

How many books are in the Chesapeake Shores series?

There are 15 books in Sheryl Woods’ Chesapeake Shores series. The most recent book was released in 2017.

Who’s in the cast of Chesapeake Shores?

Meghan Ory (Abby O’Brien)

Abby is the eldest of three daughters. The divorced mother of two is a financial analyst in New York who returns to her hometown of Chesapeake Shores. Fun fact: Meghan Ory is married to Hudson & Rex star John Reardon who is starred in Hallmark Channel movie, Love on the Sidelines.

Jesse Metcalfe (Trace Riley)

Trace is a contractor by day and a musician by night. He’s a struggling musician, depending on who you ask. He and Abby seem to have an on-again-off-again relationship though by the end of last season it seemed like they were on again. It was announced in April 2021 that Jesse Metcalfe is exiting the series. He will appear in several episodes in the first part of Season 5. While he’ll no longer be on Chesapeake Shores, fans will still see him on Hallmark. He stars in the Martha Vineyard Mystery series of movies which air on Hallmark Movies & Mysteries.

Emilie Ullerup (Bree O’Brien)

Bree is the middle of three daughters. She is a playwright and writer. Fun fact: Emilie Ullerup was born and raised in Copenhagen, Denmark. Her father is Ove Ullerup, a Danish diplomat.

Laci J. Mailey (Jess O’Brien)

Jess is the youngest of three daughters in a family with five kids. She bought a dilapidated property that she hopes to renovate and turn into a bed & breakfast.

Treat Williams (Mick O’Brien)

Mick is the patriarch of the O’Brien family. He’s a hard-working contractor whose dedication to his job became a detriment to his family.

Barbara Niven (Megan O’Brien)

Megan left her husband and children to move to New York when Abby was 17. She has since returned to Chesapeake Shores and is attempting to mend the fences she has broken. In real life, Barbara Niven is a motivational speaker.

Diane Ladd (Nell O’Brien)

After Megan left Mick, Nell helped to raise her grandchildren. Fun fact: Diane Ladd is the mother of actress Laura Dern.

Gregory Harrison (Thomas O’Brien)

Thomas is Mick’s brother and an environmental attorney. Harrison also stars in the Signed, Sealed, Delivered series of movies on Hallmark Movies & Mysteries where he plays Joe O’Toole, the father of Oliver O’Toole (Eric Mabius). Fun fact: Gregory Harrison is an avid surfer.

Brendan Penny (Kevin O’Brien)

Kevin is the eldest O’Brien son and an army vet. Fun Fact:Brendan Penny has starred in almost a dozen films for Hallmark.

Andrew Francis (Connor O’Brien)

Connor is the fourth of five children in the O’Brien clan. He shares a strong bond with his grandmother. Fun fact: Andrew Francis has been a voice actor since the age of 9 and has voiced characters in over 20 series!

Jessica Sipos (Sarah Mercer O’Brien)

Sarah is a firefighter and was previously married to a Marine. Fun fact: Jessica Sipos is the sister to Shaun Sipos, who is also an actor.

Carlos Marks (David Peck)

David Peck is a chef and hails from a wealthy family. He and Jess are dating. Peck starred in Angel Falls: A Novel Holiday opposite Jen Lilley.

Abbie and Kayden Magnuson (Caitlyn and Carrie Winters)

The real-life sisters also play sisters on the show. Abbie and Kayden star as Abby’s daughters, Caitlyn and Carrie Winters.

What happens in Chesapeake Shores season 5?

Whew! We finally get to see what happens after that kiss in the Chesapeake Shores season 4 finale! Season 5 premieres with “A Kiss is Still a Kiss,” on Sunday, August 15. Following their unexpected kiss, Abby (Ory) reflects on her relationship with Trace (Metcalfe) and what it means for her future. After insisting that their wedding take place in Chesapeake Shores, David’s (Carlo Marks, “Smallville”) parents present Jess (Mailey) with a legal document that puts her on edge. Bree (Ullerup) returns from London fresh off the run of her play and receives an intriguing job offer that would reunite her with her high school nemesis. Unbeknownst to Connor (Francis), the law firm he’s now working for may be representing a client who could be a major conflict of interest for the O’Brien family.

Is anyone new joining the cast?

Yes! In light of Jesse Metcalfe’s departure from the series, Robert Buckley will be moving to Chesapeake Shores. Who or what character he will play remains to be seen. Check back here for updates!

When will filming begin for season 5 of Chesapeake Shores?

Filming began in mid-April in Vancouver, Canada.

Is Jesse Metcalfe leaving Chesapeake Shores?

Unfortunately, yes. Metcalfe’s character Trace Riley will exit the show early on in season 5. Metcalfe will still be a part of the Hallmark Channel family as he also stars in the Martha’s Vineyard Mystery series of movies on Hallmark Movies & Mysteries.

What day is Chesapeake Shores on?

Chesapeake Shores comes on Sunday nights.

What time is Chesapeake Shores on?

Chesapeake Shores comes on Sunday nights at 8 p.m. ET.

Is Chesapeake Shores on Netflix?

Unfortunately not.

Where to watch Chesapeake Shores

If you want to catch up on Chesapeake Shores before the season 5 premiere, you’ll need Hallmark’s streaming service, Hallmark Movies Now. Seasons 1-4 are also available for purchase on Prime Video, Apple TV, YouTube and Vudu.

What channel is Chesapeake Shores on?

Chesapeake Shores airs on the Hallmark Channel.

Who sings the Chesapeake Shores theme song?

The song that is heard during the opening credits of Chesapeake Shores is called “Coming Home” by Adam Woodall.

Where is Chesapeake Shores filmed?

Chesapeake Shores is filmed on Vancouver Island just a ferry ride away from the City of Vancouver, Canada where When Calls the Heart, Signed, Sealed, Delivered and many of the Hallmark Channel Christmas movies are filmed. If you’re looking to visit the area to see some of the locations and buildings where the show has filmed, check out the Vancouver Island Tourism site.