The Hamptons Hidden Gem Families Need to Know About This Summer

Most people drive right past Madoo in Sagaponack. And honestly? That's part of what makes it special.

Tucked away on Sagg Lake Lane, the Madoo Conservancy is a historic garden established in 1967 by artist, gardener, and writer Robert Dash. It's been called "an ever-changing masterpiece" by the New York Times -- and once you walk through the entrance marked by four large stone pots, you'll understand why. It feels less like a garden and more like stepping into someone's living, breathing work of art.

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The Hamptons Before July: Three Spots to Visit While You Still Can

There's a version of the Hamptons that most people never experience -- and it happens every year in late May and early June, right after Memorial Day weekend and before schools let out and the full summer rush arrives.

The beaches are accessible. The restaurants actually have tables. The energy is relaxed in the best possible way. If you know where to go, this is genuinely the best time of year to be out here.

Here are three spots worth getting to before July changes everything.

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The Montauk Music Festival Is Back -- And It's the Best Weekend of Early Summer

15th Annual Montauk Music Festival | May 14-17, 2026

There is a specific weekend every May when Montauk stops being a place you're anticipating and starts being a place you're actually living in. For me, that weekend is the Montauk Music Festival -- and this year marks the 15th annual, presented by the Montauk Sun.

Over 400 performances. 100 acts. 40 satellite venues spread across town. Music spilling out of every bar, every patio, every corner you turn. It's the weekend the whole town feels alive in a way that's different from the height of summer -- looser, warmer, more communal. Everyone is genuinely happy to be there.

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A New Reason to Stop in East Hampton Village: The Walter Hagen Pop-Up Is Here

There's something happening on Park Place this week, and I think you're going to love it.

On Thursday, May 14, Walter Hagen is opening a pop-up shop right in the heart of East Hampton Village at 34 Park Place — and the timing couldn't feel more fitting. With the 126th U.S. Open Championship returning to Shinnecock Hills this summer, golf is having a real moment out here, and this store is leaning into it beautifully.

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Jamagansett Is the New Amagansett Staple You Need to Know About

There's a new shop in Amagansett that I think is going to become a staple out here, and I mean that in the truest sense of the word.

Jamagansett is a jam and bake shop born right here on the East End, built around local farmers and the flavors they grow. It's small, it's specific, and it's exactly the kind of place that reminds you why shopping local out here feels different than anywhere else.

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3 Outdoor Dining Spots Opening in April

April means the places you've been dreaming about all winter are finally opening their doors again.

There's something about this moment—when the Hamptons shakes off the quiet and the restaurants start turning on their lights—that feels like coming home. The air is still cool enough that you'll want a sweater at dinner, but warm enough that eating outside sounds perfect instead of optimistic.

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A Waterfront Summer in Westhampton

There's something about Westhampton that hits different. It's quieter than Southampton, more grounded than East Hampton, but still close enough to everything that makes a Hamptons summer feel complete. The village is walkable, the beaches are minutes away, and the rhythm here feels a little slower—in the best way.

This summer, I have a waterfront condo available at Westhampton Landings that captures exactly what I love about this part of the East End. It's not about square footage or marble countertops (though it's beautiful inside). It's about waking up to sunrise over the Moneybogue Canal, having your kayak ready at the dock, and knowing the village is 900 feet from your door.

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A Year Worth Celebrating

Last week, we found out we'd been recognized at Douglas Elliman's annual Ellies awards, and honestly, we're still processing it.

#1 in Rental GCI. #2 in Rental Transactions. Top 5 in Transactions overall. Top 10 in GCI. Top 15 in Volume. Diamond status, which puts us in the top 6% company-wide.

These aren't just numbers on a plaque (though the plaque is nice). They represent 125+ transactions in 2025. Families who found their place here. Renters who spent their first summer in the Hamptons. Buyers who took the leap from visiting to belonging.

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Your Shelter Island Summer: A Local Guide to Staying, Eating, and Exploring

Shelter Island is quietly becoming one of my favorite summer escapes—and I'm watching it happen in real time.

What makes it different from the rest of the Hamptons? The pace. The moment you step off the ferry, everything slows down. There's no scene to keep up with, no reservations you had to book three months out, no pressure to be anywhere but exactly where you are. It's boat life at its finest—mornings on the water, afternoons that stretch, evenings that settle in easy.

And yet, you're not isolated. A quick ferry ride puts you in the North Fork for vineyard days or Sag Harbor for marina life and more dining options. Shelter Island gives you range without the noise. It's an idyllic summer spot that still feels unspoiled.

If you've been thinking about a Shelter Island summer, here's your blueprint.

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Joe Featured: What's Really Happening in the Hamptons Real Estate Market Right Now

After more than a decade in this business and closing over 125 transactions in 2025 alone, Joe has seen the patterns, the shifts, and the moments that matter. He's watched buyers evolve, neighborhoods transform, and the market adapt to everything from interest rate swings to changing lifestyle priorities.

The roundtable brought together industry veterans to reflect on 2025 and look ahead to what's shaping 2026. Joe's insights stood out—not because they were flashy or designed to grab headlines, but because they were honest, grounded, and deeply informed by the work we do every day with real clients making real decisions.

Here's what he shared and what it means if you're thinking about buying, selling, or renting in the Hamptons this year.

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Harbor Market & Kitchen: The Sag Harbor Spot That Solves Everything

Harbor Market and Kitchen in Sag Harbor is one of those places you find once and then never stop going back to.

It's the kind of neighborhood spot that handles whatever you need without making a big deal about it. Morning coffee run for six people? Covered. Forgot about dinner and have a house full of guests? Also covered. Need provisions, a good bottle of olive oil, or just want to wander through a market that feels warm and inviting? They've got you.

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