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This is the Summer Of Westport for our family! We all couldn’t be more excited for our hands-down favorite time of year, and with all three kids swimming well now (and a year older), this summer is gearing up to be our easiest and most convenient ever! It’s also gearing up to be our most local summer in recent memory. When I decided to take on The Westport Project this year, one of the caveats was that I was going to have to be very, VERY available. Filming a reality show every week means that I simply must be around, prepared to be on camera, and ready for anything and everything to happen with this design-build project! We’re leaning into that big time, and really looking forward to hunkering down during the best time of the year to live in our awesome little town. I can’t wait to revisit some of our favorite summer haunts, as well as to discover some new ones that I’ve been meaning to check off our list. That said, we will be going a few places here and there!
Today, I thought I’d share some of our Summer plans with you guys! Please share in comments if you’re local to the tri-state area and have some recommendations not to miss for the the next few months!
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6 Weeks Of Summer Camp
My kids don’t feel ready yet for sleepaway, but without a sitter or nanny, I needed to find a very full-time camp that all three can go to every weekday! I signed them up for the most quintessential, summery summer camp ever, and I cannot wait to see how they enjoy it! Lots of their friends go to the same one, so they’re excited for that as well. It’s so fun and new to be able to send all three kids to the same place, because they’re all in that “big kid” phase!
Broadway Shows
Staying put this summer means proximity to lots of theater! We plan to take the kids to see a bunch of shows in NYC (including &Juliet, Cabaret, The Outsiders, and Hades Town) as well as some shows at local playhouses. I grew up seeing so much in the art world, and I want to recreate that with my own family as much as possible.
Horseback Trail Riding
Marlowe and I are taking a little day trip to horseback ride on some gorgeous trails, and I’m really looking forward to doing an activity with her where she takes the lead, and has the expert upper hand!!
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Beach Days
Ian and I have committed to perfecting our beach gear setup this summer, so stay tuned for lots of content around that. We don’t have a pool or belong to a club with a pool, so we’ll be taking advantage of our beautiful local beach and spending hot days at the shore with the kiddos!
Tennis???
I’ve been missing playing tennis so much since my surgery, and I can finally play again in a couple of weeks! I’m planning to try to play as much outdoor tennis as possible this summer. In fact…if anyone I know is reading this, and wants to play…hit your girl up!
Hosting Galore
I absolutely love hosting friends at our home, and the summer months are my favorite time to have parties. Without a ton of travel on our agenda, we plan to host a lot…theme nights included! I can’t wait to come up with fun menus, frozen cocktail recipes, and lots of yard games with lots of kids running around. True summer bliss!
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Miraval Berkshires
I’m going to wellness retreat Miraval in the Berkshires for my bestie’s 40th birthday this summer with a group of girls– and I cannot wait! I’ve never been there, and I’m looking forward to unwinding, exercising, eating, and wellness-chasing with a bunch of female energy. Nothing better.
Mystic, CT
Ian and I always try to make at least one weekend getaway to Mystic in the summer months. It’s such a cute town, with an amazing food scene, and we just always have a great time. Stay tuned for a travel guide after this trip, since we’ve been enough times to make me an expert at this point!
Kiddos in South Carolina
The kids will be going with Kyle to see family in South Carolina this summer for a week, and they always have a blast hanging with their (10!!!) other cousins down there. I always miss them tons, but we normally complete SO many house projects during this time, so it is all worth it. I have to start making my list of things we need to get done! LOL.
Ian’s Birthday
Ian turned 40 last summer, and we went all out! So this summer will likely be a quieter celebration. His birthday happens to be when the kids will be out of town, so we may go away someplace for a few days– just the two of us. Or maybe we’ll do a little overnight Staycation in NYC and hit up a few of our favorite museums! Birthday celebration TBD, taking suggestions!
Marlowe Turns 11
It’s kind of hard to believe that my baby girl will be turning 11 and heading to Middle School this August!! We haven’t decided what she’s doing for her birthday yet, but will most likely be a fun activity and dinner with some girlfriends.
Annual Trip To Maine
We’re taking a week at our family home in Bar Harbor at the end of the summer, and we’re super excited. Mostly because it’s going to be the first trip there where Ian is taking a full vacation and won’t have to work! We’re hoping that Mateo is a bit more of an…enthusiastic…hiker this summer. LOL. Fingers crossed!
Photographs by Julia Dags | Copyright © 2025 Happily Eva After, Inc. All Rights Reserved.
Sounds like a wonderful summer! I’m local to you and write a family travel blog..over 300 posts of family friendly activities all over America, with a heavy emphasis on New England.. I wrote a series of food trails throughout Fairfield County during the pandemic, I have tons of hiking posts all over CT, dozens of City Guides (new haven, Hartford, Mystic!), and so much more.. let me know if you ever need a rec based on interests or distance! I love to talk all things family travel (and I am not an agent and don’t sell anything!) Enjoy checking in our your little corner of the world. 🙂
A day trip with the kids. Pack a picnic basket and go to the Lavender Pond Farm in Killingworth. Such a fun day for you and the kids!
The mix of Broadway shows, beach days, horseback riding, and hosting friends feels so wholesome and joyful.
This sounds like such a fun and meaningful summer! I love how you’re balancing family time, local adventures, and creative projects—it really captures the spirit of enjoying home and community to the fullest.
Such a lovely read! Your summer plans feel so warm, intentional, and family-focused — really enjoyed going through them.
that’s sound like such a fun trip
A day trip with the kids. Pack a picnic basket and go to the Lavender Pond Farm in Killingworth.