Chesapeake Shores Books in Order: How to read Sheryl Woods’s series?

Chesapeake Shores is a series of contemporary romance novels written by Sherryl Woods (the author of The Sweet Magnolias series). The story centers on the O’Briens, a large Irish family in a small seaside town along the Chesapeake Bay, Maryland.

Everything began with Abby O’Brien Winters who returns from New York to her hometown to help save her sister’s inn from foreclosure. That’s where she finds herself face-to-face with Trace Riley, the man she left behind ten years ago. 

How to read the Chesapeake Shores Series in Order?

It’s always possible to pick up a novel in the Chesapeake Shores book series and read it independently from the others. But if you want to emerge in the world of this small seaside town and follow the characters’ development–personal and private–it’s better to read the series in chronological order, which is the same as the published order.

1. The Inn at Eagle Point – It’s been years since Abby O’Brien Winters set foot in Chesapeake Shores, but a panicked phone call from her youngest sister sends her racing home to save Jess’s dream of renovating the charming Inn at Eagle Point. There, Abby finds herself face-to-face with Trace Riley, the man she left behind ten years ago.
2. Flowers on Main – When Bree O’Brien’s screenwriting career falls apart, she flees Chicago and heads home to Chesapeake Shores. Opening Flowers on Main promises to bring her a new kind of fulfillment, but not all is peaceful and serene when Jake Collins, Bree’s ex-lover, is there waiting for her.
3. Harbor Lights – Former army medic Kevin O’Brien has come home to Chesapeake Shores in search of a haven for himself and his toddler son, and a future that’s nothing like his past. But Kevin is suddenly facing a risk he hadn’t anticipated-in the form of Main Street bookseller Shanna Carlyle.

4. A Chesapeake Shores Christmas – After years apart, Mick and Megan O’Brien are finally ready to make it official… again. Most of their grown children couldn’t be happier about their rekindled love. Only Connor is a holdout. The last thing Megan wants to do is hurt her family again. After all, is she really sure she and Mick can make it this time around?
5. Driftwood Cottage – Single mom Heather Donovan’s dreams of home and family are tantalizingly within reach when she settles in Chesapeake Shores. The welcoming arms of the loving O’Brien clan embrace her and her son. But accepting their support seems to further alienate her son’s father, Connor O’Brien. Heather’s just about given up on her old dreams. It’s going to take a lot of persuasions to make Heather believe that some dreams are worth fighting for.
6. Moonlight Cove – Jess O’Brien has overcome a lot. Now she’s ready to share the future with a man. Her friends persuade her to join a dating service-but she gets no takers! Which is fine with her childhood friend, psychologist Will Lincoln, who’s already chosen the perfect man for Jess: himself.

7. Beach Lane – In the close-knit community of Chesapeake Shores, Susie O’Brien and Mack Franklin’s “not dating” claim befuddles everyone. Susie’s thrilled when their friendship finally heats up. Then, just when happily-ever-after seems within reach, Mack loses the job he loves and Susie faces a devastating diagnosis. But O’Briens always unite in a crisis.
8. An O’Brien Family Christmas – Dating Matthew O’Brien cost Laila Riley her career and her parents’ respect. When Laila decides it was just a fling, she breaks it off. But the O’Brien family has other ideas, and they conspire to get Laila to join them on a Dublin holiday. But Laila has reservations. Matthew’s bound to be there, and she’s far from immune. What if she can’t resist temptation?
9. The Summer Garden – Falling for “Maddening Moira” O’Malley was the unexpected highlight of Luke O’Brien’s Dublin holiday. So when she pays a surprise visit to Chesapeake Shores, Luke is thrilled… at first. A fling is one thing, but forever? Given Luke’s reaction, Moira wonders if Luke, with his playboy past, is truly the family man she longs for.

10. A Seaside Christmas – As the only child of a single mom, Jenny Collins wanted nothing more than to be part of a large family like the O’Briens. Ironically, when her mother married into that family, Jenny found herself feeling more like an outsider than ever. After years in Nashville as an established songwriter, Jenny’s drawn back to Chesapeake Shores to collaborate on a Christmas production… and to make peace with the past. In reissue, the book contains the novella Santa Baby.
11. The Christmas Bouquet – For the very driven medical student Caitlyn Winters, catching the bridal bouquet at a Christmas wedding has set off an unwanted chain reaction. Not only has she fallen in love with family medicine resident Noah McIlroy, but an unexpected pregnancy threatens her well-laid plans for the future.
12. Dogwood Hill – When former pro football quarterback Aidan Mitchell comes to Chesapeake Shores to take a high school coaching job, he’s embraced by the town-especially the O’Briens. But Aidan has a secret that could alter all their lives.

13. Willow Brook Road – Carrie Winters’s home from Europe and finds herself drawn to grief-stricken Sam Winslow, who is yearning for someone to help him raise the nephew who’s unexpectedly come into his life after a tragedy.
14. Lilac Lane – Single mom Kiera Malone struggled for years to raise her three children in a small town on the coast of Ireland. Just when she’s let down her guard and allowed herself to love again, her fiancé suffers a fatal heart attack and leaves her alone yet again. Overwhelmed by her loss, she’s persuaded to visit her father, Dillon O’Malley, and her daughter, Moira O’Brien, in Chesapeake Shores. With the promise of family ties and a job at O’Brien’s, her son-in-law’s Irish pub, she takes what seems like the biggest risk of her life.

If you like our article about the Chesapeake Shores series in order, don’t forget to bookmark it! You may also want to check out the Cedar Cove series, the Virgin River series.