Everything About The Chesapeake Shores Series

Where do we even begin with Chesapeake Shores? Hallmark Channel’s Multi Generational family drama series has been a huge hit and is much loved. Sadly it will be coming to its conclusion very soon. You just can’t help falling in love with the O’Brien family. It’s so inspiring to see every family member get the happily ever after that they deserve and the family just keeps on growing, which we just adore. There’s so much you need to know about the Chesapeake Shores series – about the books, the TV show – but we’ve got it all right here. Check it out now!

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All About Chesapeake Shores

Abby O’Brien Winters (Meghan Ory) returns to her hometown of Chesapeake Shores, Maryland after receiving a panicked phone call from her sister Jess (Laci J. Mailey), who is renovating the Inn at Eagle Point. Helping her sister save the inn from closure means that she needs to come face-to-face with the past and her first love, Trace Riley (Jesse Metcalfe), who she left behind sixteen years ago.

The TV Show (Warning: Potential Spoilers Ahead!)

IMDb: 7.5/10

Episodes: 35 (as of season 5)

Chesapeake Shores is a multi-generational family drama TV series. It is based on the book series of the same name from author Sherryl Woods. The show premiered on the Hallmark Channel in August 2016 and has had a new season released every subsequent August. The exception to this though is Season 5, which was help up from 2020 to 2021 due to delays caused by the covid pandemic. The main cast consists of Jesse Metcalfe, Meghan Ory, Barbara Niven, Laci J. Mailey, Emilie Ullerup, Brendan Penny, Andrew Francis, Diane Ladd and Treat Williams.

The series follows Abby O’Brien Winters as she returns to her hometown of Chesapeake Shores, Maryland from where she was living in New York. The reason for her return to her hometown is a desperate phone call from Jess, her younger sister who has been renovating the Inn at Eagle point and has been threatened with its foreclosure.

Abby has been juggling a demanding career, recent divorce and raising her young daughters and this hasn’t left her much time to think about the town her father built. Returning to Chesapeake Shores to help her sister means that she has to deal with her fractured family once again. Her return also brings her back to Trace Riley, who was her first love until she abruptly left him sixteen years previously. At Chesapeake Shores Abby will find a troubled family dynamic and second chances at love!

Filming for the series took place on Vancouver Island’s Qualicum Beach and Parksville, British Columbia.

If you are new to Chesapeake Shores you can watch the trailer below!

Season 1

The first season premiered on the 14th of August 2016 on the Hallmark Channel. There were a total of 9 episodes in this season and this was our first introduction to the O’Brien family when Abby returns to Chesapeake Shores to help out her sister, which results in the whole O’Brien family gathering together in their hometown for the first time in a while. The final episode aired on October 9 2016.

Season 2

Season 2 arrived to Hallmark on August 6 2017. This season ran for a total of ten episodes and the final episode aired on October 9 2017.

Season 3

Season 3 premiered on August 6 2018. Again, there were ten episodes with the last episode airing on October 7 2018.

Season 4

Season 4 was slightly shorter than previous seasons, with six episodes. The first episode aired on August 25 2019 and it ran until September 29 2019.

Season 5

Season 5 returned to Hallmark after a delay due to the Covid pandemic. This season aired from August 15 2021 to October 17 2021 on the Hallmark Channel. Metcalfe stated that he would be leaving the series and that his character’s storyline would be concluded early on in season five. Actor Robert Buckley then joined the main cast for this season. There were 10 episodes in this season. For a full run down of what happened in season 5, check out our full article here.

Season 6

chesapeake shores
Image credit: Hallmark Channel

Season 6 will arrive on Hallmark this summer! On June 29 Hallmark Channel confirmed that the Season 6 premiere date is Sunday 14 August! It’s the sixth and final season and we were left with many burning questions at the end of season 5. So, we really can’t wait for this to drop so that we can catch up on the O’Brien family.

With season 6 we will prepare to say goodbye to the families and friends of Chesapeake Shores with a final send off that is due to air in the summer of 2022.

The main cast members will be returning – we can expect to see Robert Buckley, Meghan Ory, Treat Williams, Barbara Niven, Laci J. Mailey, Emilie Ullerup, Brendan Penny and Andrew Francis all making a return.

As season 5 ended on some cliffhangers we are hoping for some answers to some burning questions! Will Connor survive another health scare? What lies ahead for Megan and Mick – will she choose family or her career this time? And of course, who was it that Abby asked to “give it a try” – Jay or Evan (we know which team we are!).

The Cast

Here are the outstanding main cast members:

Jesse Metcalfe – Trace Riley. Trace is a musician and Abby’s first love from when she first lived in her hometown. He also returned to Chesapeake Shores from Nashville. After they graduated high school Abby abruptly left Trace when she moved to New York. They work through this and rekindled their love. Trace departs in season 5.
Meghan Ory – Abby O’Brien-Winters. Abby is the oldest child of Mick and Megan. She is a high-powered New York City career woman, recently divorced and the mother to two young children. When she is called back to Chesapeake Shores to help out her younger sister she decides to stay.
Barbara Niven – Megan O’Brien. Megan is Mick’s estranged wife and mother to Abby, Jess, Bree, Brendan and Andrew. The children hold a grudge against her after she left them when they were young but Megan says that she had no choice as she couldn’t stay with Mick but didn’t want to uproot the children.
Laci J. Mailey – Jess O’Brien-Peck. Jess is Abby’s youngest sister who bought a dilapidated building and is trying to renovate The Eagle Point Inn but when she gets into financial difficulties she calls her sister for help save her from bankruptcy.
Emilie Ullerup – Bree Elizabeth O’Brien. Bree is Abby’s youngest sister who was working as a playwright in Chicago. After her first play received glowing reviews she struggles to match its success. She returns home when she learns of her grandmother’s illness and hopes to overcome her writers block.
Brendan Penny – Kevin O’Brien. Kevin is the oldest son of Mick and Megan. He was previously a medic in the US Army but he returns to Chesapeake in search of a new career.
Andrew Francis – Connor O’Brien. Connor is the youngest son of Mick and Megan. He studies for a law degree and becomes an aspiring attorney.
Diane Ladd – Nell O’Brien. Mick’s mother and matriarch of the O’Briens. When Megan left and Mick was busy with work Nell became the primary caregiver and helped raise the children.
Treat Williams – Mick O’Brien. Mick is the patriarch of the O’Briens and father to Abby, Jess, Bree, Brendan and Andrew. He runs his own construction company and had to raise the children alone when his wife, Megan, left (with help from his mother).
Robert Buckley – Evan Kincaid. Evan is a successful entrepreneur who brings a development project to town. Arrives in season 5.

The Books

Before it was the much-beloved TV series, Chesapeake Shores started out as a book series. Sherryl Woods started the series with The Inn At Eagle Point in 2009, with the second and third books being released in the same year. The most recent release was Lilac Lane in 2017. Each novel follows different characters, all revolving around the O’Brien family.

Here’s the full list of books in the series:

  1. The Inn At Eagle Point
  2. Flowers On Main
  3. Harbor Lights
  4. A Chesapeake Shores Christmas
  5. Driftwood Cottage
  6. Moonlight Cove
  7. Beach Lane
  8. An O’Brien Family Christmas
  9. The Summer Garden
  10. A Seaside Christmas
  11. The Christmas Bouquet
  12. Dogwood Hill
  13. Willow Brook Road
  14. Lilac Lane

Frequently Asked Questions

Will there be a 6th season of Chesapeake Shores?

Yes, there is a season 6 of Chesapeake Shores. Chesapeake Shores season 6 will air on Sunday August 14. Season 6 will also be the final season of Chesapeake Shores.

How can I watch Chesapeake Shores season 6?

Chesapeake Shores Season will be available to stream on Hallmark Movies Now upon it’s release. It can also be streamed on Hallmark Movies now via Amazon Prime Video and FuboTV. You can also purchase season 6 to watch on AppleTV, Amazon Prime Video, Google Play store and Vudu.

Where is Chesapeake Shores filmed?

Although Chesapeake Shores is set in Maryland, which is on the east coast it is filmed on Vancouver Island.

Is Chesapeake Shores returning in 2022?

Yes, Chesapeake Shores is returning in 2022. Chesapeake Shores season 6 will air on Sunday August 14. Season 6 will also be the final season.

Was Chesapeake Shores Cancelled?

Yes Hallmark did cancel Chesapeake Shores . But the series will be given a conclusion as the sixth and last season will air in the summer of 2022.

What books are Chesapeake Shores based on?

Chesapeake Shores is based on the Chesapeake Shores Book series written by Sherryl Woods. These books are set in the beautiful town of Chesapeake Shores, Maryland and they’re full of romance, drama, and intrigue, just like the TV Show!

Does Chesapeake Shores follow the books?

The Chesapeake Shores TV series is based on the books but it doesn’t follow the book plotlines exactly. In the book series each book focuses on a different couple but the TV show mainly follows Abby’s story with the rest of the characters storylines as subplots.

What should I watch after Chesapeake Shores?

If you enjoyed Chesapeake Shores then these are shows that you should watch afterwards:

  1. Virgin River
  2. Sweet Magnolias
  3. Everwood
  4. Bridgerton
  5. Brothers And Sisters
  6. Gilmore Girls
  7. Firefly Lane
  8. When Calls The Heart
  9. Cedar Cove
  10. Good Witch
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