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At the Television Critics Association winter press tour in February 2019, it was announced that the series would return for a fourth summer season, consisting of only six episodes; a spinoff television film was simultaneously announced. The fourth season premiered on August 25, 2019.
Abby O'Brien Winters returns from New York to her hometown of Chesapeake Shores, Maryland, after receiving a panicked phone call from her youngest sister Jess, who is renovating the Inn at Eagle Point. Abby's demanding career, divorce, and young daughters have kept her too busy to even think about the town her father built. Saving her sister's inn from foreclosure means dealing not only with her fractured family but also with Trace Riley, her first love whom she abruptly left sixteen years ago. He initially is an obstacle but becomes an unexpected ally and a second chance at finding love. The troubled family dynamic is intensified when Abby's estranged mother comes back to town.
Meghan Ory as Abby O'Brien-Winters: a high-powered New York City career woman, divorcée, mother to two young daughters, and the oldest of Mick and Megan's five children. After years away from her family, she takes a trip to her hometown of Chesapeake Shores and decides to stay.
Jesse Metcalfe as Trace Riley, a musician and Abby's first love who has returned to Chesapeake Shores from Nashville. After high school, Abby abruptly left Trace and Chesapeake Shores without warning, which they had to work through upon her return.
Treat Williams as Mick O'Brien: patriarch of the O'Briens. His wife Megan left him many years ago, making him a single father working hard to provide for his family.
Diane Ladd as Nell O'Brien: matriarch of the O'Briens and Mick's mother. When Megan moved out and Mick was frequently on the road for work, Nell became the children's primary caregiver.
Laci J. Mailey as Jess O'Brien: Abby's youngest sister who has bought a dilapidated old inn that she intends to transform into a bed and breakfast. On the brink of financial disaster, she must call on Abby to save her from early bankruptcy.
Emilie Ullerup as Bree Elizabeth O'Brien: Abby's younger sister who is a struggling playwright living in Chicago. Her first play earned her glowing reviews, but she has yet to recreate its success. Her writer's block and her grandmother's illness cause her to return home.
Barbara Niven as Megan: Mick's estranged wife. Her children hold a grudge over her leaving many years ago, but she claims Mick left her no choice. She couldn't be around him, but also didn't want to uproot the children from their home.
Brendan Penny as Kevin O'Brien, older son of Mick and Megan. Initially a medic in the U.S. Army, he explores other career opportunities in season two.
Andrew Francis as Connor O'Brien, younger son of Mick and Megan who is initially a law student, and later an aspiring attorney.
Abbie Magnuson as Caitlyn Winters, daughter of Abby and Wes
Kayden Magnuson as Carrie Winters, daughter of Abby and Wes
Serge Houde as Del Granger, Abby's new boss in Baltimore
Britt Irvin as Danielle Clayman, Connor's law school classmate who becomes his love interest
In addition to playing the character Trace, Jesse Metcalfe performs some of the songs used in the series' episodes. A songwriter for more than a decade, Metcalfe also composed two of the songs himself.
Production for the second season started in spring 2017. It premiered on August 6, 2017. On January 13, 2018, Hallmark announced that the show was renewed for a 10-episode third season, which premiered on August 5, 2018.
The series premiered on the Hallmark Channel on August 14, 2016. It premiered on Canada's W Network on August 25, 2016.
Neil Genzlinger of The New York Times said Chesapeake Shores is "as well scrubbed and predictable as they come -- in other words, perfectly suited to Hallmark's target audience." He added, "fans of [Sherryl Woods's series of novels], at least, will probably enjoy seeing this annoyingly pristine world brought to life."
Gwen Ihnat of The A.V. Club gave the two-hour series premiere a B grade, praising the "ethereally gorgeous" Meghan Ory and the "acting powerhouses" of Treat Williams and Diane Ladd. She added that they "may make the show worth watching, and the giddy chemistry of the romantic leads certainly doesn't hurt."
Chesapeake Shores two-hour premiere on Sunday, August 14, 2016, was seen by 1.942 million viewers. Its largest ratings demographic were people over the age of 50, with a 1.42 share, followed by a 0.45 share among women aged 18 to 49. Over the course of the first season, the series was Hallmark's "most-watched [...] in the network's history" by women and adults in the 25-54 age demographic in its live plus three days (L+3) of DVR viewing, leading to its second-season renewal.