Chesapeake Shores Cast: Fun Facts About Your Favorite Actors

We love Chesapeake Shores and we love the Chesapeake Shores cast. The show just wouldn’t be the same without them. Since we’re such huge fans, we’ve made a fact page about all of the cast ahead of the new season (number 5), which will be released on the 15th of August. Check it out now!

Chesapeake Shores airs on Hallmark Channel. Click here to check out all the ways you can watch Chesapeake Shores to catch up >>

Estimated reading time: 9 minutes

Jesse Metcalfe (Trace Riley)

Much to our disappointment, Metcalfe stated that he would be leaving the series and that his character’s storyline would be concluded early on in season five. 

Chesapeake Shores cast Jesse MetcalfeBirthday: December 9, 1978

His parents are of European descent

Metcalfe was born in California, but his father is of English, Irish, French, and Italian descent and his mother is of Italian and Portuguese descent. 

He dropped out of university

Metcalfe graduated from The Williams School in New London, Connecticut, then went on for further education at New York University. Once he booked the part of Miguel Lopez-Fitzgerald on the soap opera Passions, he dropped out.

Metcalfe fell off a second-story balcony 

In November 2008, he hosted the World Music Awards in Monaco. At an after-party, he fell off a second-story balcony and fell 30 feet to the ground. Ouch! Luckily, he only fractured his fibula and avoided a more serious injury.

Meghan Ory (Abbie O’Brien-Winters)

Chesapeake shores cast: meghan oryBirthday: August 20, 1982 

She’s been in a lot of films and shows

If you think Ory looks familiar, it might be because she was Red Riding Hood/Ruby in Once Upon A Time, Sherry Woods in Vampire High, Riley Neal in Intelligence, and so much more. She’s been in the movies John Tucker Must Die and Dead Rising: Watchtower, both with Chesapeake Shores co-star Jesse Metcalfe. 

She’s married and has children

Ory is married to John Reardon, who she starred in Merlin’s Apprentice with two years before they married. They have two children together, born in 2018 and 2019.

Her parents didn’t let her start a career in acting straight away

From the age of 8, Ory knew that she wanted to do acting. She was a member of her local theater and loved every moment on stage. Although, she was only allowed to start auditioning when she was old enough to make responsible decisions and had a good education as a back-up.

Barbara Niven (Megan O’Brien)

Birthday: February 26, 1953

She started her acting career late

Niven was in her 30s and was a single mother when she started acting. And she definitely did not have it easy. In the early 80s, Niven auditioned to replace the character Tina Lord on One Life to Live. There was a nationwide search and she attended the audition in Seattle, without telling anyone. She was called up to New York for a screen test, where the casting director told her that her voice would only lead to victims’ roles. So she took voice classes from a retired radio host. Then, in 1986, she was cast in Hallmark Hall of Fame’s Promise.

She is a motivational speaker

Niven has spoken at schools, professional groups, and on TV shows. Some of her topics include: “Giving up Perfect to Claim Your Dreams”, “Paralyzed to Powerful”, “Eating Disorders & Pressures to be Perfect”, and “The Pressure to be Thin in Hollywood”. She also speaks out against bullying.

Niven is an animal rights activist

She has adopted a lot of cats and dogs, and fosters old animals. Niven has participated on an animal rescue team to save victims of a puppy mill and is a National Ambassador for American Humane.

Chesapeake Shores Cast – Laci J. Mailey (Jess O’Brien)

Birthday: 15 November, 1990

Mailey likes to do pottery

On her Instagram, Mailey is always posting things she’s made out of clay! From pots to dishes, Mailey has made so much. We wish we were as good as her at pottery. 

She’s married to her boyfriend of 11 years

Mailey is married to Steve Bradley. They were dating for 11 years before they tied the knot. They also have a son, Cassius Leo Bradley, who was born in 2019.

Chesapeake Shores Cast – Emilie Ullerup (Bree O’Brien)

Birthday: 27 October 1984

Ullerup is Danish

She was born in Copenhagen, Denmark to a diplomatic family. Ullerup speaks both Danish and English. Her father held the title of Lord Chamberlain for the Danish Royal Family.

She moved from Copenhagen to Vancouver in 2003

After finishing high school in Denmark in 2003, she moved to Vancouver and attended Vancouver Film School, where she graduated in 2005. Her first role was in the remake of Battlestar Galactica in 2006. One of her most famous roles – aside from Bree, obviously – was as Ashley Magnus in Sanctuary in 2008-2010.

Chesapeake Shores Cast – Brendan Penny (Kevin O’Brien)

Birthday: November 9, 1978

Penny had a minor part in John Tucker Must Die

Whilst Metcalfe was the main role in the movie and Ory had a fairly big part, Penny played Teammate #1. Penny was also in an episode of Supernatural. Ullerup, Ory, Mailey and Andrew Francis also starred in different episodes of Supernatural too!

He is Canadian

Like much of the Chesapeake Shores cast, Penny was born in Canada. He grew up in both Ottawa and London (in Canada). He attended Fanshawe College in London, Ontario and earned a BS in accounting. Later, he went to the Lyric School of Acting, in Vancouver, British Columbia, where he had moved to in 2002 to pursue a career in acting.

Chesapeake Shores Cast – Andrew Francis (Connor O’Brien)

Birthday: May 27, 1985

He does a lot of voice acting

And when we say a lot, we mean it! Francis has been doing voice acting since the age of 9. He’s voiced Shining Armor in My Little Pony on multiple occasions and Bail Organa in LEGO Star Wars. And he has voiced characters in the English dubs of some anime, like Dragon Ball Z, Inuyasha, Gintama and more. Francis has even voiced Judau Ashta in the video game series Dynasty Warriors: Gunham. 

Chesapeake Shores Cast – Diane Ladd (Nell O’Brien)

chesapeake shores cast: diane ladd
Diane Ladd with her daughter Laura Dern

Birthday: November 29, 1935 

She’s won a BAFTA

For her performance in the 1974 film Alice Doesn’t Live Here Anymore, she won the BAFTA Award for Best Actress in a Supporting Role. And she went on to win the Golden Globe Award for Best Supporting Actress on Television for her role in Alice in 1980-81.

Her daughter is an actress as well

Diane Ladd had her daughter, Laura Dern, with Bruce Dern, who she starred with in The Wild Angels. Laura Dern is best known for her role as Dr. Ellie Sattler in the 1993 Jurassic Park. 

Chesapeake Shores Cast – Treat Williams (Mick O’Brien)

Birthday: 1 December, 1951

He was in an episode of The Simpsons

In 2012, he played himself/William Sullivan in The Simpsons episode “A Totally Fun Thing That Bart Will Never Do Again”. 

He’s a certified flight instructor

In 1969, his high school football coach, who was also a flight instructor, offered to train him in a Piper Super Cub. At the age of 21, he was a private pilot. And he became a FAA instrument-rated commercial pilot. As a result, he had privileges in both single engine and multi-engine airplanes as well as rotorcraft helicopter. He owns many different types of planes, which he uses for family travel between homes. 

Chesapeake Shores Cast – Robert Buckley (Evan McKenzie)

Robert Buckley will be joining the main cast in the upcoming season.

Birthday: May 2, 1981

He was almost Captain America

In 2010, Buckley was reported to have been running for the title role in Captain America: The First Avenger. But, the part went to Chris Evans instead.

Buckley has a degree in economics

Graduating with his economic degree in 2003, Buckley attended the University of California. After which, he worked for a year as an economic consultant, before moving back to LA to pursue a career in acting. And whilst he was a college student, he appeared on The Price is Right. 

He’s been in a lot of big roles

If you think you recognize Buckley, you might have seen him as: Kirby Atwood in Lipstick Jungle, Clay Evans in One Tree Hill, Brian Leonard in 666 Park Avenue, and Major Lillywhite in iZombie. 

Which of these facts are your favorite? Let us know!

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Chesapeake Shores Cast: Fun Facts About Your Favorite Actors
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