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.

Memorial Day weekend didn't exactly deliver on the weather front. Most people spent more time watching the radar than actually being outside. But while the skies were doing their thing, a few openings happened quietly — and they're worth knowing about before summer really gets going.

The North Fork doesn't get enough credit from the Hamptons side. It's right there -- cross Gardiners Bay and in under an hour you're pulling into Greenport, which has a completely different energy. Slower, a little scrappier, genuinely charming. It makes for a perfect day trip, and doing it by boat makes the whole thing feel like an event.

Here's exactly how to do it.

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.

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.

My friend has been saying it for years: Hampton Bays has a different vibe. Less scene, more vacation. Less about being seen, more about actually relaxing. And she's completely right.

If the Hamptons ever starts to feel like a performance, Hampton Bays is the antidote. And Rumba is exactly where you go to feel that shift.

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.

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.

Navy Beach opens April 24th, and if you've been waiting for the perfect sunset spot in Montauk, this is it.

I love Navy Beach for so many reasons—the setting, the food, the fact that it works for date night, dinner with friends, or the whole family. But mostly, I love the flexibility of it.

The announcements are starting to roll in, and suddenly summer doesn't feel so far away anymore. Between returning favorites and exciting newcomers, here are three openings we're marking our calendars for.

If you're out here this weekend, there's a good mix happening—live music, a new village-wide celebration, a parade, and an Oscars watch party. Here's what's worth knowing.

Spring in the Hamptons isn't just about warmer weather—it's about the return of the places that make the season feel real. The restaurants that have been closed all winter, the patios you've been dreaming about, the meals that remind you why you love it here. This year, I'm counting down the days for three seasonal favorites that signal spring has truly arrived.

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.

There are certain stores in the Hamptons that feel less like shopping and more like coming home. Breezin' Up is one of them.

If you've never been, it's the kind of place where everything is soft, sun-faded, and impossibly comfortable—the sweatshirt you reach for on a cool beach morning, the tee that feels like it's already been broken in by a hundred summer days. It's been family-run since 1984, and you can feel that in every piece. Nothing here is trying too hard. It all just... fits.

Hot chocolate in the Hamptons isn't just a drink. It's a ritual. It's what you order after a beach walk when the wind has stripped all the warmth from your body. It's what you sip slowly in a corner booth while the snow piles up outside. It's permission to slow down, to stay a little longer, to let the day unfold without urgency.

Here's where to find the best versions this weekend, each with their own distinct approach.

There's a particular kind of magic that happens when a village decides to celebrate winter instead of simply enduring it. This Saturday, Sag Harbor does exactly that with HarborFrost, the beloved winter festival returning for its 15th anniversary.

If you've been out here long enough, you know that winter in the Hamptons asks something of you. It asks you to slow down, to notice the light differently, to find beauty in bare branches and icy harbors. HarborFrost is the village's answer to that ask—a day that transforms the cold into something worth gathering for.

There’s a very specific kind of quiet that settles over the Hamptons after a snowfall.

The roads empty. The beaches go still. And suddenly, winter doesn’t feel like something to get through—it feels like something to lean into.

When the forecast starts whispering snow, these are the places I’m already picturing. Not because they’re the only good spots—but because they’re the ones that feel cozier, warmer, and more special when you arrive with cold cheeks and snow on your boots.