By Kerry Mastrobuoni
Every Journey begins with a single step, but it isn’t always the destination that shapes us; it’s the direction we choose each day.
That’s why I’ve called this column Kerry’s Compass.
A Compass doesn’t tell us how fast to travel or what challenges lie ahead; it simply points us toward true north.
It’s been many years since I last put my thoughts on paper. Somewhere between marriage, raising children, work, friendships, family gatherings, and keeping up with the beautiful chaos of everyday life, writing quietly found its place on the back burner. Not forgotten, just patiently waiting.
Now, as life begins to slow down in the best possible way, it feels like the perfect time to begin writing again.
So welcome to Kerry’s Compass.
If you know me, you probably know there’s no better place to start than
The End – Montauk.
There’s a certain magic that begins the moment you cross into town. The air feels different. It’s as if the Atlantic has a way of reminding you to breathe a little deeper.
Montauk has changed over the years. It’s no secret that influencers, luxury hotels, and social media have transformed this once-quiet fishing village into one of the East Coast’s trendiest destinations. Prices have climbed right alongside its popularity, and yes, a weekend in peak summer can leave your wallet noticeably lighter.
But here’s the secret seasoned Montauk lovers already know: you can still experience its charm without spending a fortune. Visit midweek, come after Labor Day when the crowds thin, or sneak away during the shoulder season. The beaches are just as breathtaking, the sunsets just as spectacular, and you’ll often discover the Montauk that locals have loved for generations.
Some of my favorite memories have been made over long dinners at Duryea’s, where the waterfront views somehow make time stand still. Cocktails at The Crow’s Nest have become a tradition, with its effortless coastal charm and twinkling lights that make every evening feel like summer should never end. And then there’s The Montauket, perched high above the water, where locals and visitors gather together to watch one of the most spectacular sunsets on Long Island. It truly never gets old.
Beyond the well-known favorites lies the history that gives Montauk its soul. The iconic Montauk Point Lighthouse that has stood watch since 1796, guiding ships through changing tides for generations. Wander the quiet trails of Camp Hero, explore hidden beaches tucked away from the crowds, or simply take a scenic drive to discover the corners that don’t always make it onto Instagram. Those are often the places that stay with you the longest.
That’s what I hope Kerry’s Compass becomes—a place to share destinations worth exploring, hidden gems waiting to be discovered, and stories that remind us why we travel in the first place. Sometimes the greatest journeys aren’t measured in miles but in the memories they leave behind.
And for me, this journey begins exactly where it should.
At The End!
I’d love to hear from you! Share your travel tips, ideas, and inspiration at Kerryscompass@longislandmediagroup.com. Until next time, always let your compass lead you somewhere worth remembering.
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