First Impression: Chesapeake Shores (2016)

Welcome back to First Impression, our brand-new Girls Gone Hallmark series where we’re revisiting Hallmark Channel pilot episodes and sharing our hot takes! This week, Megan and Wendy are back with episode two, bringing their signature commentary – from cast chemistry and cozy vibes to whether the show passes the all-important Hallmark Test. Here’s our First Impression: Chesapeake Shores;

Listen to First Impression: Chesapeake Shores (2016)

What is Chesapeake Shores About?

Chesapeake Shores follows the emotional journey of Abby O’Brien Winters, a high-powered career woman and divorced mother of twin daughters, who reluctantly returns to her hometown after years away. When her younger sister Jess calls in distress Abby finds herself drawn back to the picturesque Maryland coastal town her father built.

Returning to Chesapeake Shores means confronting the painful memories she left behind and reconnecting with her fragmented family. As Abby works to save her sister’s inn from foreclosure, she unexpectedly crosses paths with Trace Riley, the man whose heart she broke a decade ago. What begins as a challenging reunion gradually transforms, as Trace becomes not just an unexpected ally in Abby’s efforts, but potentially offers her a second chance at love she never anticipated.

Set against the stunning backdrop of the Chesapeake Bay, this heartwarming story explores family bonds, second chances, and the possibility of finding home again in the place you once fled.

When did Chesapeake Shores Premiere?

Chesapeake Shores premiered on August 14, 2016 on Hallmark Channel. The first episode was movie-length at 1 hour and 21 minutes long.

Who is in Chesapeake Shores?

• Chesapeake Shores was created by Nancey Silvers and John Tinker.
  • Nancy has 31 writing credits including all 55 episodes of Chesapeake Shores. In addition she wrote Love at the Thanksgiving Day Parade and The Nine Lives of Christmas.
  • John Tinker has 18 writing credits. In addition to being credited on all 55 episodes of Chesapeake Shores he also wrote on When Calls the Heart and 138 episodes of Judging Amy for which he was also the creator.
• Meghan Ory stars as Abby O’Brien Winters. Megan has 45 acting credits including a long running role as Red Riding Hood on Once Upon a Time as well as the currently airing series Sullivan’s Crossing.
• Barbara Niven plays Megan O’Brien. Although we don’t meet her until the end of the episode she remains a star of the series throughout it’s run. Barbara has 115 acting credits and can be see in her role as Delores Swensen in the Hannah Swensen Mystery movies.
• Laci J. Mailey plays Jess O’Brien. Laci has 31 acting credits and has recently been seen in The Perfect Setting and Betty’s Bad Luck in Love.
• Emilie Ullerup plays Bree O’Brien. Emilie has 57 acting credits. For Hallmark she was in Retreat to You in 2023 and she played the role of Ruby Franke in Mormom Mom Gone Wrong: The Ruby Franke Story.
• Treat Williams plays Mick O’Brien. Treat has 132 acting credits and you might remember him from his role as Dr. Andy Brown on the series Everwood in the early 2000’s. He has a total of 132 acting credits, and before his tragic passing in 2023 he was in series like Feud and Blue Bloods.
• Diane Ladd plays Nell O’Brien. Fun fact: Diane will turn 90 this year and is the mother of actress Laura Dern. She has a long resume of 132 acting credits.
• Jesse Metcalfe has 32 acting credits which include the soap opera Passions, Desperate Housewives, and the Martha’s Vineyard Mysteries series for Hallmark.
• Although Brendan Penny doesn’t appear in this episode, he plays the role of Kevin O’Brien in all future episodes. Brendan has 61 acting credits and has done a ton of work since Chesapeake Shores. You can find him in The Wedding Cottage, In Merry Measure, A Novel Noel, and A Season for Family to name just a handful of his credits.
• Andrew Francis plays Connor O’Brien. Like Brendan his character was played by another actor in the pilot of the series. Andrew has 233 credits although since Chesapeake Shores he hasn’t been seen on Hallmark. Previously he was in Engaging Father Christmas and Coming Home for Christmas.

We’re Your New Hallmark Besties

Hey there! We’re Girls Gone Hallmark! Megan’s a longtime Hallmark movie fan, while Wendy – well, she used to be a Hallmark hater. Now, we’ve teamed up to share our (often very different!) takes on these films. Get ready for some lively, fun-filled conversations!

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