‘Chesapeake Shores’ Season 2 Review

I appreciated Chesapeake Shores in its freshman year, but the show took an incredible turn this season making it that much more unforgettable. Normally, while I’m under the belief that TV shows tend to flop in their second season making it the weakest one, Chesapeake Shores season 2 did the exact opposite, and I’m thankful for the team of writers who’ve chosen to tell stories through the eyes of the characters. I’ve always said that a TV show is much stronger when episodes are driven by the characters as opposed to the plot and in season two, we were given the chance to love the O’Brien clan even more than before as they told their realistic, encompassing stories through tremendous heart and innate growth.

Most Noteworthy Performance by an Actor:
Brendan Penny

When we were introduced to Kevin O’Brien last season, I never once imagined that he’d end up being my favorite character on the series. There are a number of things that are impressive about the growth Kevin went through during Chesapeake Shores season 2, but I’m essentially in awe of the series’ choice to address PTSD as they have. And Brendan Penny performed his heart out in each episode rising to every challenging emotion with pristine stamina and a full range of emotions.

You expect a character with Kevin’s background to have experienced some level of post traumatic stress, but for some unspoken reason, show runners don’t explore it with the depth that they should, and that’s why Kevin’s arc is so special — the series gave him the platform to slow down for a moment and that’s a lesson all the O’Brien children needed to learn. Life isn’t about our careers or who we marry or where we live, it’s about molding our characters into the best version of ourselves that we can be. And with everything that he went through last season, it was Kevin’s moment to unravel all the possibilities that could make him better. No one has it all together, and the second oldest O’Brien sibling is no exception to the fact, but Kevin’s goodness is so rare, it forces you to question how he can’t have it all — he deserves it, but the truth is, sometimes the most sincere souls have to go through the most turmoil.

As the season forced Kevin to question where he wants to be in life, it also brought a potential a love interest in the picture whose crosses, in different ways, were as traumatic as his, and after everything he went through last season with Georgia, learning to trust again, with the help of his family showcased his bravery remarkably. It takes great strength to trust love again after it’s done its part to mess with a person’s heart. (But serious question, does this mean Sarah’s all in now? While the choice to kiss him could indicate that she’s changed her mind, it doesn’t change the fact that she’s been sending him mixed signals all throughout the season. But also, who wouldn’t be all in for Kevin O’Brien? His kindness towards his family has left me absolutely floored.) And with each confusing sign Kevin received, each road block in his path, Penny gave us a glimpse into Kevin’s state of mind with a myriad of emotions. It allowed us to see life through the eyes of those who believe it’s their duty to protect the world, and it allowed us to understand that it’s these very people who deserve protection most. And I appreciated the fact that when he was able to slow down, Kevin realized that he doesn’t want to be doctor, but rather a paramedic — it revealed to viewers that our choices, in spite of what people think are what matters most, and Kevin finally choosing for himself was the illumination of the kind of growth everyone needs to go through — learning to be good to ourselves while remaining selfless when it comes to our treatment of others. The full range of emotions Penny projected — whether it was the organic display of a man at his wits or the acute happiness in the face of good times, whatever Kevin felt, we did, too and it was the noteworthy performances, episode after episode, that helped us get to know the character profoundly.

Most Noteworthy Performance by an Actress:
Laci J. Mailey

Jess has been a remarkably fascinating character since her very first appearance, but this season, I appreciated just how much Laci J. Mailey made sure we were given the chance to get to know the character further. And the choices she’s made throughout the season have easily left me caring tremendously for her. In Chesapeake Shores season 2, Jess finally found love, forgave her mother, and successfully managed the Inn with less mishaps than before.

Jess is a vital character for a number of reasons but she easily stands because of the fact that she doesn’t always have it together. And part of writing strong women on television is directly correlated with writing real women, and very seldom do we see someone like Jess, which is why she’s easily became my favorite. Sometimes, we leave things on the stove for too long. Sometimes, we forget. Sometimes, we can’t let things go. Sometimes, we’re wild. Sometimes, we’re quiet. Women are such multifaceted characters that writing us as we are makes it them that much more viewable. And Mailey brought each of these organic traits to life masterfully through the inexplicable sincerity she tirelessly brought to the table.

And that’s it — Jess’ sincerity is an art in and of itself that ceaselessly lightens the screen in a poetic array of emotions. Whatever Jess experienced, we felt it and it was entirely due to the heartfelt performances Mailey put on week after week. In Jess’ happiness we were able to find glimpses of hope, and in her heartache, we understood the horrifying pangs of goodbyes. And that’s why “Freefall” was such an exemplary episode for her — this is now Jess’ moment to bask in hope in spite of her sadness. In order to grow more, she must find the means to move forward believing that David meant every word he spoke. This is her moment to fall freely into what’ll be the best years of her life because she’s taking control with the belief that in spite of her flaws, she’s loved by many. With the help of her family, friends, and her own inimitable conscious, Jess has grown profoundly this season, and I hope we get to see more of the innate, childlike sincerity govern her path as she dives in to the next chapter of her life. Whatever challenges await, we can be certain Mailey will take them on remarkably delivering a wide range of relatable, raw emotions each time.

Honorable Mention:
Meghan Ory and Emilie Ullerup

In the same way that Mailey delivered incredible performances week after week, so did Meghan Ory and Emily Ullerup — so impeccable that I couldn’t bear to choose between the women because I felt like Grandma Nell would argue against me. The O’Brien sisters faced challenges after challenges in Chesapeake Shores season 2 with each actress delivering the emotions with astounding grace and realism. Ory and Ullerup in their own unique way have allowed their characters to tell their stories through lenses that have proven to be relatable and complex. These are incredibly wonderful, brave women with a number of emotions within them and their means of expression and growth have been awe-inspiring.

Best of the O’Brien’s: The best of the O’Briens has consisted of marvelously sappy moments around a fire and honest conversations about life. And this season especially dealt with opening up the cans of worms that were left under their beds for years. The confrontation of their demons taking place with s’mores and gentleness made me the happiest of souls because really, I’m in awe of the conversations the kids are willing to have. And since we’re given the chance to see that Mick isn’t on good terms with his brother, the kids maintaining their bond through integrity and openness reveals the fact that conversations solidify bonds beautifully.

Boy or girl it never mattered because they were able to confide in one another about anything and everything leaving them easily content in the midst of chaos. From relationships to careers, the sole understanding between them and the choice never to judge has stood out remarkably. While both platonic and romantic relationships have a tendency to get ugly, the O’Briens consciously making the choice to be there for one another with the occasional friendly taunting is how we should all aspire to be. Whether it was the brotherly bond between Kevin and Connor, or the brothers with their sisters, or the girls with their moments alone, family time on this show is the gift that keeps on giving. This season, the O’Briens faced it all — from Kevin choosing his career path, to Connor quitting his job, Jess successfully managing the Inn, Bree managing the book store, and Abby learning to balance work with family time — the sole fact that they can each speak up about their issues and know that their siblings will never judge is the gift that’s bound to teach viewers that not only is no one perfect, but there’s strength in vulnerability. And their strengths are revealed through the expression of their choice along with the choice to ceaselessly be there for one another through everything.

Chesapeake Shores is by no means a perfect show, but the choice writers have made to tell stories through the characters has made it exceptional. It’s essentially what’s gripped me, and it’s what has made season two so special. My only concern is that the finale left us with more questions than answers, but if there’s a season three, than I’m not opposed to its temporary conclusion. The O’Briens are special, and their stories are special — their likes/dislikes, quirks/flaws, their weaknesses and their strengths all deserve to be explored. And each character on this show deserves to have their story told as they dive heart first into happiness.

Extra Thoughts:

  • Who else wants to know more about Grandma Nell’s mystery man? That scene broke my heart.
  • Who else wants to see Mick and Thomas patch things up? It seemed like they were headed towards that direction in the end so here’s to hoping.
  • You know what I would love next? Chesapeake Shores fall edition or a Christmas movie, I’ll happily take either.
  • I don’t know about anyone else, but the fashion on this show, especially for the women is on point week after week.
  • Ugh, how cute are all the couples on this show? It’s seriously too much to handle at this point because it’s an overload of adorable.

What are your thoughts on Chesapeake Shores season 2? If there’s anything you’d like us to discuss, let us know in the comments below.


  1. I’m a few years behind with this comment, but seeing as we’re about 2 weeks out from the premiere of S5, I just wanted to share how much I enjoy and agree with this review; Bree and Kevin are definitely my favourite O’Brien siblings, with Jess coming a very close second, and a large part of that is due to how their stories have been written from the very beginning to now (though I have to admit that I don’t think I’ve ever been so excited for Bree’s storylines as I am for her romantic possibilities in S5!!)

    I’ll also wanted to ask whether you’ve seen S3&4, what you thought of them, and what your level of excitement is for S5?

    1. Aw thank you. I’m glad you enjoyed years later. I had a lot of mixed feelings about S3&4 mainly because I really didn’t enjoy Trace’s storyline at all and it got very redundant, so I’ll be honest in admitting that I am more excited now for season five than I was before. I’ve adored Robert Buckley since One Tree Hill, so I’m very intrigued with his character and what he’ll bring to the table. Depending on how the season premiere plays out, I might actually review the episodes weekly so, we’ll see. I absolutely adore Kevin, Jess, and Bree as well, and I can’t wait for their arcs. And Abby just deserves so much. So ultimately, I’ve got higher expectations now and hope we won’t be let down.

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