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KATIE KENNEDY

What’s Happening This Summer

May 23, 2025

What’s Happening This Summer
📍 Bedford, New York

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Top || Jeans || Wedges || Handbag || Earrings || Lip Color

Summer always has a way of sneaking up on me—one moment it’s April and we’re layering trenches over sweaters, and the next, I’m pulling linen dresses from the back of the closet and stocking up on SPF. We kicked off the season with a sun-drenched brunch at the Bedford Post Inn, and ever since, the weeks ahead have been filling up faster than expected. While I typically like to keep summer plans loose and breezy, this year is shaping up to be delightfully full of movement, memory-making, and a few new destinations I’m especially excited about.

Memorial Day in the Hamptons

We’re welcoming the unofficial start of summer with a weekend on the East End. Although the weather is expected to be unseasonably cold, I’m looking forward to s’mores in the backyard, exploring and shopping in the quaint towns, and crisp glasses of rosĂ©. There’s something timeless about the Hamptons this time of year—before the true summer rush begins.

Celebrate the Jaws 50th Anniversary

Fun fact about me: Jaws is one of my all-time favorite movies and this year marks 50 years since it first made a splash in theaters. To celebrate, we’re heading over to Westerly, Rhode Island for a Jaws screening and celebration. There’s a nostalgic thrill in revisiting a classic in the place so close to what inspired it all. Plus, it’s the perfect excuse to explore the Ocean State with a fresh lens.

A Girl’s Weekend in Palm Beach

Fingers crossed this one comes together, because a girls’ getaway in Palm Beach sounds like just the thing for a mid-summer reset. Think: matching robes, cocktails by the Colony Hotel pool, and lots of laughs over seafood towers and shared sunscreen. We’re dreaming of cabana stripes, vintage shops, and morning walks along Worth Avenue.

Relaxation and Rum in Barbados

This will be my first time visiting Barbados, and I’m already envisioning warm nights, lush greenery, and that signature Caribbean pace that encourages you to slow down and sip something tropical. We’re planning to split time between lounging at Cobbler’s Cove and light exploring—maybe even a boating day if we’re feeling adventurous.

A Family Wedding on Lake Winnipesaukee

We’re heading to Lake Winnipesaukee for a family wedding this summer, and I’m especially excited about the charming historic schoolhouse we’ve rented—it looks so peaceful and tucked away. I’m looking forward to quiet mornings, exploring more of New Hampshire, and of course, raising a glass on the dock to celebrate the happy couple.

Ending the Summer at the Weekapaug Inn

Returning to Weekapaug Inn feels like closing the season with a deep exhale. It’s becoming a fast favorite family tradition—long walks on the Atlantic, easy dinners by the lawn, and maybe one last round of pool time before the start of fall begins. It’s one of those places where everything slows down, in the best way.

And somehow, there’s even more on the horizon—dinners with friends, spur-of-the-moment day trips, maybe a surprise or two. How did the summer season get so packed? I’m not complaining, just trying to soak it all in, one crisp glass of rosé and lobster roll at a time.

Love from New York,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England. 

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