Calling all Chessies! Hallmark Channel fans have laughed, cried and loved alongside the cast of Chesapeake Shores since 2016 — and offscreen, fans have become equally as intrigued by the stars’ friendships and love lives.
When Chesapeake Shores debuted, viewers were introduced to the lovable O’Brien clan after eldest sister Abby O’Brien (Meghan Ory) moved back home following her divorce. With her two children in tow, Abby was reunited with sisters Bree (Emilie Ullerup) and Jess (Laci J Mailey), as well as brothers Kevin (Brendan Penny) and Connor (Andrew Francis).
The family wouldn’t be complete without mom Megan (Barbara Niven) and dad Mick (Treat Williams), who often led by example as to what true love looks like. The romantic ups and downs of all the O’Brien children has hooked fans season after season, with Abby’s love life being a main focal point.
In May 2021, Jesse Metcalfe, who played Abby’s high school sweetheart Trace Riley, surprised viewers when he announced his exit after five seasons. “I tailor-made that role for me,” Metcalfe exclusively told Us Weekly in October 2020, ahead of his final bow. “I mean, the series is based on a series of books, where the character is an architect. So, I was given the liberty to completely change the character and kind of make [him] just, like, [me].”
New love interest Evan Kincaid (played by Robert Buckley) was quick to fill the void but left many fans wondering if Abby would find her happily ever after. In August 2022, Chessies got their answer as the sixth and final season of the beloved series began.
The 10-episode finale, however, wasn’t the last fans would see of the O’Brien clan — because the cast are great friends outside of the show. In fact, many of the stars have already gushed over their bond after wrapping filming on the series.
“Well that is a wrap on #chesapeakeshores after 6 seasons! I started this season with #hyperemesisgravidarum and ended it with #covid — it has been quite the run!” Ory wrote via Instagram in July 2022. “Thank you so much to our amazing cast and crew for having so much patience with me while I tried not to barf on anyone.”
The Once Upon a Time alum also gave her “amazing” husband John Reardon a shout-out for “holding down the fort and being my rock.” She added: “And our two, yes two Nannie’s for all their support. With mom and dad both on tv shows, two Nannie’s was a must! #ittakesavillage. I hope everyone that watches enjoys the final season! Xo.”
Ory’s TV sister Ullerup also got sentimental after saying goodbye to her work family that same month. “For six years I got to play these wonderful, nutty people’s daughter, sister and brother. It is the longest running job of my career,” she wrote alongside a group snap. “So much happened in our make-believe world and also in our personal lives. It was a wonderful cushion to have a whole second family to share the ups and downs with.”
The Love & Glamping actress — whose real-life spouse Kyle Cassie appeared on several episodes of the show as Martin Demming — concluded: “I know they will all move onto great things as they are truly talented people. I will forever be grateful for all that #chesapeakeshores gifted me with. What a great run, fam.”
Scroll down for a complete guide to the cast’s real-life romances: