The Hamptons Edit Our Insiders Swear By This Summer

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Laura Corrigan of The Agency maps out 16 essential stops from East Hampton to Montauk, plus detours to Sag Harbor, Southampton, and Shelter Island. Here's what makes this insider guide worth saving.

There's a version of the Hamptons that shows up in glossy magazines, all golden hour and private beach access. And then there's the version you actually need — the one where you know exactly where to stop for coffee between showings, which detour is worth the extra miles, and why the East End keeps pulling people back year after year. Our SVP of Marketing & PR and Executive Editor of The Agency Magazine, Laura Corrigan, just mapped out that smarter version for Observer. She covered 16 stops from East Hampton through Montauk, with a few worthwhile detours to Sag Harbor, Southampton, and Shelter Island. It's the kind of list you save to your phone before you hit the road. ### Why the Hamptons Still Matter The Hamptons have always run on two economies — real estate and taste — and they've never really been separate. The same families who built the first summer cottages after the railroad reached the South Fork in the 1870s are the reason the region still gets written about today. That history isn't just charming; it shapes everything from property values to where the best lobster roll actually lives. You can feel it when you drive through the villages. Each one has its own rhythm, its own set of unwritten rules. Knowing those nuances is what separates a good visit from a great one. ### Tastemakers, Not Just Participants Our PR and marketing team has built a reputation as tastemakers in this world, not just participants in it. That's exactly why one of our own was tapped to write the Observer's newest guide to the East End. Media prowess, in this case, doubles as market intelligence. When you spend your days immersed in the local market — the listings, the buyers, the seasonal shifts — you start to notice patterns. You know which neighborhoods are warming up before the crowd does. You know where to send clients for a quiet dinner that isn't a scene. That's the kind of insight you can't Google. ### Year-Round Local Expertise With headquarters in New York City and offices planted throughout the Hamptons, The Agency's connection to the East End goes beyond the summer months. We're there in February when the beaches are empty and the fireplaces are lit. We're there in October when the light turns that specific gold that only happens in autumn. That year-round presence means we don't just know the market — we know its seasons, its characters, and its hidden corners. It's the difference between giving directions and giving context. ### What You'll Find in the Guide Laura's guide isn't about the obvious spots. It's about the smarter way to spend a weekend, with stops that locals actually rate. Here's a taste of what she prioritized: - **East Hampton**: The classic village energy, but with a few unexpected finds - **Montauk**: Worth the drive for the food and the unfiltered coastal vibe - **Sag Harbor**: A quieter detour with serious charm and history - **Southampton**: Where tradition meets a fresh, modern pulse - **Shelter Island**: The escape within the escape, if you have the time Each stop was chosen for a reason — not just because it's popular, but because it delivers something real. ### The Takeaway The best weekend in the Hamptons isn't about cramming in every famous spot. It's about moving with intention, knowing where to linger and where to skip. That's the kind of expertise that comes from being embedded in the community, not just visiting it. Read the full guide on Observer — An Insider's Guide to a Smarter East Hampton Weekend, With the Right Detours. And if you're thinking about making the East End more than a weekend thing, our team knows exactly how to help you find your place in it.