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The Hallmark Channel romantic series "Chesapeake Shores" shares the stories of the O’Briens, a family that always finds hope in their enduring love for one another as they each navigate their lives, loves, and careers. The Hallmark Channel editorial team has compiled their top ten favorite episodes spanning the first five seasons of the show. Subscribe to Hallmark Movies Now to catch up and watch every episode of the series now!
Click through and discover the top 10 episodes and can't miss moments to get you up to speed!
#10 – “Pilot” Episode 1 of Season 1
Abby, a busy professional and single, working mom heads back to her hometown of Chesapeake Shores at the request of her sister, Jess. Once back at her grandma Nell’s home with her young daughters Caitlyn and Carrie, Abby learns the reason that Jess needs her help. The grown sisters visit Jess’ new bed and breakfast, and then to the bank to try to get Jess an extension on a loan. At the bank, Abby runs into her former boyfriend, Trace and tensions simmer between the two. Abby and Jess’ father Mick, an important developer and longtime resident returns from out of town and is excited to see Abby and the girls. Jess is not the only one building a dream – Trace has ownership of the beach shack he always wanted, and Abby goes to visit him there. She offers a heartfelt apology for leaving town without saying goodbye years earlier. As the weekend unfolds, Abby faces the truth about past regrets and sees that in her overscheduled life she is missing out on what really matters.
Can’t miss moment: Trace takes Abby to a favorite spot from their earlier years together and the two share a romantic moment.
#9- “Second Chances” Episode 7 of Season 1
A handsome and friendly stranger approaches Bree at the lending library and the two share a few minutes talking about literature, and a love for reading. Bree does not catch his name, but seems intrigued. Mick has purchased an abandoned warehouse that he has had his eye on for years. Trace approaches him about using it for a music venue and Mick is open to the conversation. In a tense meeting with Abby, ex-husband Wes reveals that he is being investigated by the SEC and has lost just about everything, and that he needs Abby’s help. Mick and ex-wife Megan bicker about the past and their roles in raising the children, and Megan’s abandonment. When Abby discovers a long-lost guitar belonging to Trace in the back of her childhood closet she returns it to the owner. Trace reveals the real and terrible reason that he left Nashville, and Abby comforts him in his distress. Connor takes Kevin for a fun joyride in a golf cart on the beach and the two bond beneath a fort they built together as children. Kevin begins to talk about his injury sustained in the line of duty in Afghanistan, but is too traumatized to finish the story. There is an awkward meeting when David, Jess’ new date officially meets Bree at a dinner that David and Jess are hosting. He is the handsome stranger she met at the lending library!
Can’t miss moment: Kevin’s outing with Connor comes to an abrupt ending when Kevin takes a bad fall and may have hurt himself further.
#8 “Exes Mark the Spot” Episode 9 of Season 1
Jess has suffered from a terrible dream that has haunted her for years, and she finally comes clean to Megan about its recurrence in her life. After seeing how happy his girls are in Chesapeake Shores, Wes decides to drop the custody battle for his daughters and give full custody to Abby who is relieved and happy. Mick is managing a problematic building project with his partner Darryl. Connor has an exciting interview in Baltimore. Jess is convinced that breaking it off with David is the right thing as she sees the romantic chemistry and common interests that he and Bree share. Complicating matters, she offers David a job as the chef for the B & B and he could not be more thrilled. Kevin confides to Connor that he has made two big decisions – one to return to medical school and two that he is not ready to be a husband to Georgia. Bree is faced with a big decision as well when her ex-boyfriend Martin shows up and announces a big opportunity for Bree should she choose to accept it.
Can’t miss moment: An abrupt police arrest takes one character by complete surprise.
#7 “Pasts and Presents” Episode 2 of Season 2
While Trace continues to work on his new album with Leigh, he reassures Abby that the connection with Leigh is strictly music. Jess is excited to be hosting a beautiful wedding for her second cousin at the B & B. Megan is moving and renting a house in Chesapeake Shores and Kevin is helping out and continuing to work through his PTSD. Mick breaks the bad news to Trace that he has to sell the music club in order to focus on the O’Brien family trust, and that he has gotten an offer already. Trace is understandably upset and Abby vows to talk to her dad to try to get him to change his mind. Bree visits Chicago to work with Martin on her new play and finds herself at odds with decisions being made about her script.
Can’t miss moment: Abby discovers a photo with a mystery man and learns of a very close yet distant relative…
#6 “Freefall” Episode 10 of Season 2
Emotions run high in this finale episode for season 2. At the insistence of John, the Trace Riley Band goes back to the table with Mark to work on a deal for the band. He is able to offer the group a six-month tour in Europe as an opening act, but Trace is not sure about leaving behind his obligations in Chesapeake Shores. Much to Jess’ dismay, David is quitting his job as the B & B chef and will be departing shortly to spend more time with his family. Mick and Thomas continue to wrestle with the O’Brien land trust when Douglas steps in as an investor, and Mick is determined to have the development deal go through despite Thomas’ objections. Simon has lost Bree’s trust after submitting her manuscript without permission, and Bree makes the painful decision to move on from the relationship.
Can’t Miss Moment: David comes clean to Jess about his real identity and why he is leaving town.
#5 “Here and There” Episode 6 of Season 3
When Caitlyn and Carrie make a special breakfast for the family, they share that their dad’s new girlfriend Terri is teaching them how to cook. Abby is surprised, but wants to put her best foot forward and invites the new couple to dinner in Chesapeake Shores. Meg shares that she has a new job offer in New York, and Mick seems angry and disappointed at the news. Later, the two discuss a future that includes building a new relationship between them. Simon is back in Chesapeake Shores and lets Bree know that he is there out of a desire to be closer to her. Trace is helping his father to prepare for retirement, and shares his feelings about the emotional neglect he felt as a child. David returns and wants his old job back at the Inn after turning down the offer to take over the Peck business ventures. The extended O’Brien family enjoys a dinner together and Mick offers a welcoming toast to all of the new friends at the table.
Can’t Miss Moment: Simon surprises Bree with a gesture that leaves her speechless.
#4 – Before a Following Sea Episode 10 of Season 3
After much deliberation, Trace decides to move ahead with the tour to Europe and Asia with his band. Though Abby is determined that Trace should follow his dreams, she is devastated at the thought of Trace leaving her and the girls. After careful consideration, Abby decides to end the relationship and the two share a painful goodbye. Kevin and Connor take a trip to Philadelphia to visit Sarah, where Kevin tells her he has applied for a job in the city to be nearer to her. She is touched, and seeks out her old job in Chesapeake Shores to return the favor. The two exchange a message of true love. David and Jess receive an unexpected offer from David’s parents – they want to buy them a new B & B in Tanglewood to manage together. Megan has read Bree’s manuscript and offers her daughter a heartfelt apology for the damaging decisions she made in the past that hurt the family.
Can’t Miss Moment: Gran shares wisdom from the heart with Abby.
#3. The End is Where We Begin – Episode 1 of Season 4
Kevin is mulling over a marriage proposal, and his sisters weigh in with their feelings. Trace is back in town from the tour and keeps trying but failing to connect with Abby. In the meantime there is a new songwriter performing at The Bridge, his music club, named Emma and Trace takes on the role of mentor. Bree finally meets a director she can connect with, Hannah, who will direct her new play. Jess and David come to an agreement to leave Tanglewood and return to Chesapeake Shores to start again and rebuild the inn. Trace finally meets up with Abby during a morning run, but she is evasive and reluctant to talk about a reunion.
Can’t Miss Moment: Kevin and Sarah share a huge moment over a flat tire!
#1 Watercolors, Wishes and Weddings - Episode 6 of Season 4
Bree is at a professional high point when her play opening concludes with a standing ovation. She meets Brian, who wants to be her agent, and take her play for a run in London. Connor has accepted a new job with an important firm and shares the news with his Uncle Thomas. Megan and Mick continue to talk about what the future may hold for them. Jess discovers an engagement ring in a drawer in the kitchen of the Inn, and waits impatiently for David to pop the big question. The two run into a legal issue when they opened for business accidentally before officially having their permit in place, and go to city hall to plead their case. Jay and Abby continue to get to know each other, but in a lunch out together they encounter Trace and Emma. Jay understands it is best to take things slowly.
Can’t Miss Moment: When Abby heads to the beach to clear her head, she finds Trace playing a new song, but the sentiment is nothing new to either of them.
Kevin and Sarah are thrilled to find out that Sarah is indeed pregnant. They agree to keep the news under wraps during the first trimester, but it may be difficult to hold off on sharing with the family. Mick receives a package with an urn of ashes and an anonymous note from a long lost friend with a very specific request. Abby does some research and discovers it is Buzz, a former bartender at a Chesapeake Shores bar, The Windjammer. Mick remembers him fondly and decides to honor his request. Megan receives a visit from an influential art critic Carter Millburn. The two work on getting permissions for the Driscoll exhibit to open, and their chemistry throws Mick off balance. Abby gets “whisked away” by Evan and he surprises her with an unexpected helicopter ride to one of his “getaways.” Tensions simmer between Bree and Luke when Jerome reveals that Luke spent three years in prison. After a painful confrontation, Luke attends a class Bree is teaching and participates in the writing exercise about who he was, and who he wants to become. The two share a kiss and the future seems brighter for the pair.
Can’t Miss Moment:
Evan has an important proposition for Abby, but it does not concern what she expected!