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.

When the Hamptons gets a big snowstorm, everything slows down in the best possible way. Roads go quiet, the beach turns white, and suddenly everyone’s asking the same question:

Where do we sled?

If you’ve got kids (or you’re a kid at heart), grab your sled, pack some hot chocolate or cider, and head to one of these local favorites. These are the hills people actually use.

There's a particular kind of afternoon that only exists in the off-season Hamptons. The one where the village feels like it belongs to you, where you're not navigating crowds or waiting for tables, where the light hits Main Beach in that low, golden way that makes you stop mid-step just to take it in.

This is that afternoon. Five stops, no rush, just moving from one intentional moment to the next.

Winter in the Hamptons has a quieter rhythm—but every so often, there’s an experience that reminds you just how magical the off-season can be.

LongHouse Illuminated is one of those moments.

Each winter, LongHouse Reserve transforms its iconic gardens into an immersive evening celebration, inviting visitors to explore art, performance, and storytelling under softly glowing lights. It’s not a traditional holiday event—and that’s exactly what makes it special.

Winter in the Hamptons has a quiet kind of magic. The crowds thin out, the pace slows, and suddenly the places that feel warm, welcoming, and timeless really shine.

When the temperatures dip into the twenties and you’re craving something cozy—but still special—The Palm in East Hampton is one of those places that never misses.

Winter in the Hamptons has a different kind of magic.

It’s quieter, slower, and more intimate — the kind of season where you linger a little longer at the table, take colder beach walks, and notice the details that summer rushes past.

That’s exactly what inspired our Hamptons Homes & Seasons Winter Guide.

If you’d like a complimentary printed copy mailed to you, you can request one below. We prepare these in small batches and send them out as they’re ready.

Hanukkah begins Sunday evening, and throughout all eight nights, the Hamptons will be illuminated with moments of light, joy, and community.

Hosted by the Jewish Center of the Hamptons, Pop-Up Hanukkah brings menorah lightings to meaningful places across the East End — from village parks to restaurants and cultural landmarks. Each night offers a slightly different atmosphere, but the heart of the celebration remains the same: gathering together to mark the Festival of Lights.

If there’s one event that defines December in East Hampton Village, it’s SantaFest—two full days of holiday sparkle, small-town charm, and that unmistakable out-east magic. And this year, the celebration returns bigger, brighter, and bursting with festive moments for every member of the family. Consider this your complete guide so you don’t miss a single highlight.

Most people don’t think “Hamptons” and immediately picture the Northern Lights — but the last few days have proven (again) that this coast always finds new ways to surprise us. Montauk lit up with soft greens and pinks this week, and if you know where to look, winter here can bring a few more of these rare, electric nights.

We were lucky enough to catch them last year, and I swear: it’s one of those moments that stops you in your tracks and reminds you why life out here feels a little enchanted.

Here’s everything you need to know if you want a shot at seeing them this season.

Thanksgiving in the Hamptons hits different—cozy kitchens, crisp air, and a whole lot of hosting. But here’s the thing: you don’t need to be the hero who makes every dish from scratch. Outsourcing dessert is not only allowed… it’s the smartest move you can make.

If you want pies that feel homemade without the meltdown, these are the spots locals rely on year after year.

In a place as beautiful and abundant as the Hamptons, it’s easy to forget that many of our neighbors quietly face food insecurity. Behind the farm stands and market baskets are hardworking families, seniors, and individuals who sometimes struggle to put food on the table. The truth is, food insecurity doesn’t just happen “somewhere else.” It’s here—right in our own towns, among people we know. And if there was ever a moment to step up for one another, it’s now.

Thanksgiving weekend in the Hamptons feels like a secret — quiet beaches, cozy restaurants, and that soft golden light that makes the East End feel even more peaceful. Whether you’re hosting at home or sneaking away for a long weekend, here’s your complete guide to Thanksgiving in the Hamptons 2025 — from the best turkey on the East End to beautiful ways to spend the holiday.

Halloween in the Hamptons feels different — a little cozier, a little more small-town magic. Between the fall foliage, crisp evenings, and community celebrations across the East End, there’s something for everyone — from family-friendly traditions to after-dark parties that last well past midnight.

Here are five can’t-miss ways to celebrate Halloween weekend in the Hamptons this year.

There’s a quiet kind of magic that happens in the Hamptons each fall — when the fields turn golden, the pace slows, and the community gathers not for glitz, but for gratitude.

One of the most meaningful local rituals of the season is the Lantern Walk at Amber Waves in Amagansett — a heartfelt evening that celebrates the close of another abundant harvest.

Last weekend, while visiting the Strasburg Railroad in Pennsylvania with our kids, I did a double take. There it was — the unmistakable green Hampton Jitney pulling up beside the train station.

Every October, just as the summer crowds fade and the light turns golden, the Hamptons International Film Festival (HIFF) transforms our quiet villages into a vibrant celebration of cinema. Whether you’re a seasoned festival-goer or just looking for a special way to experience the Hamptons in the fall, here’s everything you need to know.

The Hamptons has a rhythm all its own. The light shifts, the crowds ebb and flow, and with each new season, the East End reveals a different side of itself. Over the years, we’ve found that some of our most treasured memories weren’t made in the height of summer, but in the quiet, in-between moments — a golden hour walk through empty streets, a chilly sunset at the beach with blankets in tow, the first fire crackling in the fireplace.