Homes & Seasons HAMPTONS
FROM JENNA’S desk
Winter on the East End has its own kind of magic. December arrives with twinkle lights, menorah glow, village traditions, and the small-town charm that makes the Hamptons feel like a Hallmark movie. It’s the sweetest, most nostalgic season — the one where you bundle up, wander through town, and actually run into people you know everywhere you go.
But after the holidays fade, winter shifts. The pace slows, the crowds thin, and the days stretch a little quieter. And that’s when the real beauty begins. January, February, and March invite you to create your own magic — the kind that’s softer, slower, and somehow even more meaningful.
It’s the first morning you see snow on the beach. It’s a walk at Maidstone under a gray sky that looks like a painting. It’s a mug of something warm after a cold-water surf session. It’s letting time breathe again.
Some of our favorite winter moments are the simple ones — a bonfire at the bay on a mild day, making s’mores with the kids while the sun dips low, bundling up for a beach walk, or watching Prince Harry race across the dunes. Slower days don’t mean less life; they just mean you actually get to notice the good parts.
And yes — sometimes winter feels a little too long, and that’s why learning to slip away for a few days (hello, Palm Beach and Anguilla) is part of the rhythm too. A little sunshine doesn’t take away from winter here… it makes you appreciate it even more when you come home.
This season is about presence, peace, and finding the pockets of joy tucked into the quieter months. It’s about savoring the Hamptons in a way you can’t in July — when the world slows down just enough for you to fall back in love with this place all over again.
a note from joe Joe
The holiday season in the Hamptons arrives like a quiet blessing. In December and January, the pace softens. The landscape exhales. Life slows just enough for you to hear the wind move through the pines and the ocean breathing in the distance.
Most mornings begin before dawn, when the world is still half-asleep and the house is wrapped in silence. I slip out at 5:45 a.m., tired but grateful for the stillness. By 6, I’m in the pool at the YMCA—dark sky overhead, water holding the last trace of night. The first immersion always takes me by surprise, then settles into something familiar and steady.
Halfway through my laps, a thin beam of sunlight breaks the horizon and lands on the pool floor, scattering gold into my foggy goggles. That single sunray feels like a small miracle—proof that I’ve met the day early, moved through the darkness, and greeted the light in motion.
Stroke after stroke, breath after breath, I remind myself that the world can wait a little longer. Work, calls, responsibilities—they all stand patiently outside the sanctuary of the water. And when I finally step into the winter air, it rushes into my lungs, sharp and clean, and it feels like a second awakening.
Winter out here becomes a season of connection. Listing appointments, new clients, new stories—everything grows a bit more gently this time of year. And in the quieter moments, we return to the people who anchor us: our family, our friends, our clients. We take stock. We give thanks.
We’re grateful to share our magazine again this season, filled with the places, moments, and inspirations that color our lives in the Hamptons —especially during these soft, reflective winter months when the light comes slowly, and every small joy feels like a gift.
out east WINTER MOMENTS
Winter out East has its own rhythm — slowed down, wide open, and full of small moments you miss in the rush of summer. The beaches are quiet, the wildlife comes out, and all the trails that feel packed in July turn peaceful and golden. These are the places we return to every year when we want that crisp, quiet magic only the Hamptons can give you.
At the Elizabeth A. Morton National Wildlife Refuge in Noyac, winter might be the most magical season of all. Bring a small handful of seeds, hold out your palm, and within seconds chickadees and nuthatches will flutter down and eat right from your hand. The trail winds through dunes and bayside marshes, with soft winter light and some of the calmest views you’ll find anywhere.
WHEN THE CROWDS FADE, THE REAL BEAUTY SHOWS UP
Over in Montauk, it’s peak seal-watching season. On calm, cold days you’ll see them hauled out across the sandbars at Lazy Point and Napeague, or bobbing past the rocks at Montauk Point. Local naturalists host guided seal walks throughout the winter, sharing the best vantage points and giving you a closer look at why these beautiful animals migrate to our coastline each year.
Winter also transforms our hiking trails. With the leaves down, the water views open up and every path feels twice as expansive. The Ranch in Montauk is all rolling hills and big skies; Cedar Point Park gives you rugged coastline and long, quiet loops perfect for a weekend reset. And for an easy bayside wander, Barcelona Neck Preserve is gorgeous at golden hour — a favorite for families, photographers, and anyone craving fresh air.
And when we inevitably get that first real snowfall, there are two non-negotiables out here: sledding at Quail Hill in Amagansett — the closest thing we have to a winter amusement park — and a walk on the beach while the dunes are covered in white. The ocean looks completely different in winter light, and there’s something about the quiet, the crunch of snow on sand, and the wide-open shoreline that resets you instantly. These are the small winter rituals that make the off-season feel like its own kind of magic.
EVENTS & FESTIVALS ALIVE where winter comes
Winter in the Hamptons may be calmer, but it’s far from quiet. The season comes alive with village celebrations and festive moments that draw the community together long after summer fades.
Each November, the Montauk Lighthouse transforms into a glowing beacon, marking the start of the season.
Families gather on the bluff for carols, cocoa, and the first sparkle of the holidays as thousands of lights flicker to life against the Atlantic. The lighthouse remains illuminated through the winter, casting its steady glow long after the last note of music fades — a reminder that the East End never truly goes dark.
THE EAST END SPARKLES ALL SEASON- FROM GLOWING VINES TO FIREWORKS OVER FROZEN WATERS
In Sagaponack, Wölffer Estate’s Lighting of the Vines adds a touch of glamour to the season. Beneath the soft hum of live music, guests sip mulled wine and watch as the vineyard bursts into light, row by row. The evening benefits The Bridgehampton Child Care & Recreational Center — a local nonprofit that supports families and children across the East End — giving this sparkling celebration a deeper warmth. The vines stay lit all winter long, so even on a quiet February afternoon, you can cozy up by the fire with a glass of rosé and a view of the sleeping vines.
By mid-winter, just when everyone’s craving a little energy, Sag Harbor delivers. HarborFrost arrives on the perfect February weekend — a jolt of joy in the heart of the cold. The village fills with live music, ice sculptures, and fire dancers, drawing neighbors out from hibernation. The night ends with fireworks over the frozen harbor, where the bursts of color bounce off the ice and snow in a dazzling reflection of winter’s rare beauty.
And in East Hampton, LongHouse Illuminated transforms the sculpture gardens into a glowing dreamscape. The art, trees, and pathways shimmer under soft washes of color, inviting visitors to wander after dark and see this beloved space in a whole new light. It’s peaceful, surreal, and uniquely East End — where nature and creativity meet under winter skies.
ICE SKATING and coastal calm
There’s a particular energy to winter in the Hamptons that shows up the moment the ponds freeze — the scrape of blades across ice, kids racing each other at dusk, and the kind of neighborhood buzz that only happens when the cold brings everyone outside. It’s winter at its most playful, where sound and movement replace the hush of the off-season.
If you’re extremely lucky, Town Pond in East Hampton turns to glass, and locals appear with thermoses and skates in hand.
Children play pickup hockey after school while parents watch from the edge, bundled in scarves, sipping something warm. There are no tickets, no lights, no soundtrack — just laughter, the scrape of blades on ice, and the kind of community charm that makes winter feel like home.
For a guaranteed glide, Buckskill Winter Club offers the classic East Hampton experience — a charming open-air rink strung with twinkle lights and the scent of hot chocolate drifting through the cold. Lessons, hockey, and public skates fill the day, but it’s the simple moments — hands in mittens, cheeks flushed, cocoa breaks by the fire pit — that make it unforgettable.
WHEN THE ICE GLEAMS AND THE SUN SETS EARLY, THE HAMPTONS FEEL LIKE A SECRET YOU’RE LUCKY ENOUGH TO KEEP.
And when the skating’s done, head toward the bay. As the sun dips early behind the dunes, the sky turns watercolor pink and gold — the perfect time to wrap up in a blanket by a beach bonfire, cocoa or mulled wine in hand, and watch the light fade over the water. Winter here asks you to slow down — to breathe, to savor, to feel the quiet beauty of it all.
And just down 27, the Southampton Ice Rink carries that same old-fashioned spirit — an easygoing spot where locals gather for lessons, open skates, and weekend DJ nights. It’s relaxed, family-friendly, and the perfect stop before or after a cozy meal in town.
COZY DINING and lush vibes
There’s nothing quite like stepping out of the cold and into a restaurant that feels instantly warm — the low lighting, the clink of glasses, that first wave of heat that hits your cheeks. Winter dining on the East End is all about refuge and ritual, the spots we find ourselves craving as soon as sweaters come out and the nights grow long.
In East Hampton, The Tavern at 1770 House is basically winter in restaurant form. Downstairs, the ceilings are low, the fire snaps, and there’s that tiny fourseat bar that feels like a secret if you can snag it. Order the meatloaf or any of their cold-weather specials, and you’ll understand why locals hide out here until spring.
The Palm is a totally different vibe but somehow just as comforting — the oldschool steakhouse glow, the martinis, the bar that’s always a little louder (in a good way) on a chilly night. It’s the place you go when you want a proper dinner and to see a few familiar faces.
WINTER OUT HERE ISN’T ABOUT HIBERNATING — IT’S ABOUT FINDING THE PLACES THAT MAKE YOU WANT TO STAY A LITTLE LONGER.
When you want winter to feel beautiful, make your way to Gurney’s. Their igloos perched over the ocean don’t even feel real — waves crashing below while you’re wrapped in blankets with a cocktail in hand. It’s cozy, festive, and honestly one of the best winter experiences out here.
Over in Amagansett, Il Buco Vita stays open yearround and leans into the season with pasta, braises, and those soft, candlelit evenings that make you want to linger. They lean into holiday menus too — the kind of meals that make you feel wrapped up in the season.
Out in Montauk, Harvest on Fort Pond becomes a locals’ winter spot. It’s quiet, warm, and surprisingly romantic when the summer crowds vanish. Keep an eye out for their off-season specials — they always sneak in something good.
And if you’re closer to Westhampton Beach, Fauna is the move. It’s intimate without trying too hard, with a menu that changes just enough to keep things interesting. It feels like a treat, but still cozy enough to be a winter regular.
THE RHYTHM of winter
When winter settles over the Hamptons, the whole pace shifts. The rush of summer disappears, replaced by quiet streets, slower mornings, and the soft hum of a true coastal off-season. Yearround restaurants take their much-needed breaks — often closing for a week or two without updating their hours online — and most shops move to a five-day schedule. If you’re planning a visit, weekends are when everything really wakes up.
It’s a slower season, but that’s the beauty of it. This is when you see the local community most clearly. Every errand turns into a familiar face. Every coffee line feels like a tiny reunion. The Hamptons doesn’t disappear in winter — it becomes more intimate, more neighborly, and deeply rooted in the people who live here year-round.
Winter also brings some of the best surf of the year. Locals suit up in full drysuits and paddle out even on the coldest mornings, catching clean, powerful winter swells with frost still on the sand. It’s a reminder that life here doesn’t stop with the seasons — it just adapts.
Of course, it’s still a coastal New York winter: gray, damp, windy, and colder than you expect. Pack warm layers, waterproof boots, and be ready for the weather to shift quickly.
GRAY SKIES, COLD SURF, WARM FIRES: THAT’S THE
RHYTHM OF WINTER OUT EAST
It’s the perfect time to keep fire logs stacked by the door, candles lit, and your favorite local Cabernet within reach. Winter here isn’t about rushing — it’s about settling in and letting the season slow everything down.
THE HOLIDAYS on the East End
There’s something about the Hamptons during the holidays that feels straight out of a storybook. Every town dresses up for the season — Main Streets lined with glowing Christmas trees, lampposts wrapped in garland and ribbons, window displays twinkling in the early dusk.
Even the beaches get festive: you’ll walk past a quiet snow-dusted bench and find a holiday wreath tied to the back. It’s charming in that effortless, small-town way, but elevated in that unmistakable Hamptons way — thoughtful, cozy, and designed to make the whole season feel special.
In Montauk, the fourth-annual Magic of Montauk Holiday Fair lights up the town green with vendors, live music, hot cocoa, Santa meetand-greets, and even live reindeer — a full weekend of coastal holiday joy.
Hanukkah has its own beautiful rhythm on the East End. Each night of the holiday, East Hampton Village hosts a traveling menorah lighting, with different local businesses opening their doors to the community. One of the most beloved traditions is the candle lighting at Nick & Toni’s — warm, intimate, and always packed with families and familiar faces. It’s a moment that feels deeply local: simple, meaningful, and rooted in the spirit of gathering.
The restaurants join in too, adding their own glow to the season. Il Buco Vita’s Christmas Eve Feast of the Seven Fishes is a cherished favorite — elevated, elegant, and exactly the kind of holiday meal people remember. And for New Year’s Eve, you’ll find two very different but equally iconic celebrations: the luxe oceanfront party at Gurney’s Montauk and the lively, music-filled night at The Stephen Talkhouse, each capturing a different side of that unmistakable Hamptons holiday energy.
EVERY VILLAGE GLOWS A LITTLE BRIGHTER IN DECEMBER
What makes the season so magical, though, is the way it blends quiet moments with lively ones. Mornings spent wandering decorated streets with a latte and afternoons exploring wintry beaches with the sun glittering off the water. Everywhere you go, you can feel the community — familiar faces, local families out for traditions they’ve had for decades, shop owners greeting everyone by name. December here has its own sparkle, and it lingers long after the crowds fade.
It’s the perfect time to lean in: stroll the villages, shop the markets, linger over long meals, warm up at a cozy pub, pop into a bakery for holiday treats, or plan a festive night out. Whether you’re here for the celebrations, the coastline, or the quiet magic that settles over everything this time of year, the holidays in the Hamptons feel like stepping into a season that somehow slows you down and sweeps you up all at once.
Holiday Happenings
The holiday season out East comes alive through the events themselves — big, small, and unmistakably Hamptons. SantaFest is the centerpiece: thousands pack into East Hampton Village to watch Santa arrive by helicopter, a moment that’s both hilariously over-the-top and incredibly charming. Herrick Park fills with dancers, stilt walkers, doughnuts, cocoa, andeveryfamilyyouknow.
Montauk brings its own sparkle with the Magic of Montauk Holiday Fair, where Anchored Candy Shop’s snow machine creates a mini winter wonderland on the town green. Kids run between the reindeer pen and the cocoa stand, local vendors line the path, and the whole thing feels like a seaside Hallmark movie. And whether or not you make it to the Lighthouse Lighting, seeing the lighthouse glowing through New Year’s is worth the driveeverytime.
THE BEST OF THE HOLIDAYS OUT EAST
Across the East End, beloved traditions fill the season with warmth — Wölffer’s vineyard glowing after Lighting of the Vines, nightly Hanukkah pop-ups hosted by local favorites like Nick & Toni’s, festive markets, wreath workshops, and even a cozy holiday screening of Elf with treats from BonBon. Each event has its own personality, adding up to a December that’sjoyful,lively,anduniquelyHamptons.
SIP & STROLL EAST HAMPTON VILLAGE
A festive evening of shopping with cocktails, Dickens Carolers andfestivedecorations.
SANTAFEST
A full day of holiday magic: Santa arrives by helicopter, Christmas Parade, and North PoleBar.
MAGIC OF MONTAUK
Snow machines, live reindeer, local vendors and treats while you meet Santa in the heart of Montauk.
LIGHTING OF THE VINES
Stunning event at Wölffer Estate Vineyard. Tickets sell out fast, but the winery’s holiday decor alone isworthavisitinDecember.
POP UP HANUKKAH
Nightly menorah lightings hosted by local businesses-- intimate, warm and beloved by the community.
FEAST OF THE SEVEN FISHES
Several restaurants host this Italian Christmas Eve feast, but we love the elevated experience atIlBucoAlMare
HERRICK PARK TREE LIGHTING
A classic East Hampton moment with community cheer, holiday music and often a celebrity guest.
SOUTHAMPTON HOLIDAY FAIR
Artisans, kid’s crafts, treats and local vendors-- the perfect stop for holiday gifts and small town charm
LIGHTS OF LOVE
A heartfelt community gathering at Ashawagh Hall to welcome the seasons & light the historic SpringsChristmastree.
WINTER escapes
Palm Beach
When winter starts to stretch a little too long on the East End, sometimes the best way to appreciate the season is to step out of it for a moment — a quick dose of sun, warmth, and ease before slipping back into cozy Hamptons life.
And for anyone who’s done the Hamptons-to-JFK grind, escaping from Islip MacArthur Airport feels like discovering a cheat code. It’s close, calm, easy to navigate, and you’re through security before you’ve even finished your coffee.
That ease sets the tone for the trip — low stress, low effort, and suddenly you’re landing somewhere bright and warm, wondering why you ever traveled any other way.
SOMETIMES THE EASIEST WAY TO LOVE WINTER IN THE HAMPTONS
IS TO LEAVE IT FOR A WEEKEND.
Palm Beach is our go-to when we need a quick reset: no passport required, direct flights, and the kind of sunshine that melts winter off your shoulders in minutes.
It feels like a southern cousin to the Hamptons — polished, coastal, a little glamorous — and you’ll run into more familiar East End faces than you’d expect.
We love The Colony for its whimsical, pink-washed charm, especially since it’s the sister hotel to The Hedges back home in East Hampton, which is currently under renovation but remains an icon.
It’s also the quickest mood-shift I know — two hours in the air and suddenly you’re drinking a spritz by the pool wondering why you put up with gray skies for so long.
Palm Beach just knows how to make winter feel glamorous again.
IN SEARCH OF sunshine
For something more far-flung, Anguilla is an island we return to again and again. My parents discovered it years ago, and it still feels wonderfully under the radar — probably because getting there requires a little adventure.
Our favorite route is flying into St. Martin and taking the ferry over. Nothing kicks off a vacation like stepping onto an island, being handed rum punch, and cruising across turquoise water toward a slower pace.
Some of our best memories there are the simplest: meeting Calvin on his boat, zipping over to Little Bay, snorkeling with sea turtles, and spending a whole afternoon floating in water so clear it doesn’t seem real.
IN ANGUILLA, TIME SLOWS UNTIL ALL YOU HEAR IS THE OCEAN...AND MAYBE BANKIE BANKS PLAYING IN THE DISTANCE.
And then there was the night we visited Bankie Banks, the legendary Anguillian musician whose venue is a must-do. He’s famously played at Stephen Talkhouse in Amagansett — proof the Hamptons follows you everywhere in the best way.
If we’re not exploring, we’re usually unwinding at Aurora Anguilla, a laid-back luxury stay with an incredible golf course and family friendly water adventure park.
The island is expanding its runway to accommodate more direct flights, but for now, it still feels like a secret.
And on our bucket list is Uruguay, the winter escape every Hamptons local is quietly buzzing about — especially with the Mostrador team (yes, the Montauk legends) having deep roots there.
Golden beaches, bohemian towns, and a culinary scene that mirrors everything we love about East End simplicity.
LOOKING AHEAD Summer 2026
57 Sammy’s Beach
The 2026 rental season is already shaping up to be another incredible summer on the East End, and here’s just a small preview of what we’re bringing to the market. Think elevated beach living with truly special backdrops: 57 Sammy’s Beach Road in East Hampton, where the sand is your front yard and the panoramic waterfront views stretch from sunrise to sunset. It’s the kind of spot that makes you slow down, breathe deeper, and savor every quiet morning and golden-hour walk along the bay.
We’re curating the full spectrum of Hamptons summer living—whether it’s the sleek, architectural lines of 63 Highview Drive in Sag Harbor, a modern masterpiece with views that feel like art, or the classic Amagansett charm of 4 Cranberry Lane, complete with a peaceful pool and that timeless coastal ease everyone craves in August. This is just the beginning of what’s ahead, and we can’t wait to share the full lineup with you.
Just sold
On a serene waterfront lane in Sag Harbor sits a home designed for easy, everyday luxury. With sweeping bay views, refined updates, and outdoor spaces meant for slow mornings and golden-hour evenings, it strikes the perfect balance of comfort and coastal beauty.
THE MAGIC OF THE HAMPTONS ISN’T JUST IN THE VIEWS- IT’S THE LIFE YOU LIVE IN THEM.
Multiple waterfront vantage points make the home feel connected to nature in the most peaceful way. Launch a paddleboard from your shoreline, linger on the deck with coffee, or host summer dinners overlooking the bay. It quietly encourages you to slow down and savor the moment.
Just minutes from Sag Harbor Village and close to beloved farm stands, vineyards, and beaches, this location blends privacy with easy access to everything you love about the East End..
MAKING THE HAMPTONS PART OF your story
For us, real estate has always been about more than just properties — it’s about helping people find their place in the Hamptons in whatever way feels right. Maybe it’s a summer rental that becomes a tradition, or a first home where new memories can unfold. And often it’s during the calm of winter — when the beaches are quiet and the light feels a little softer — that people find the clarity to start something new.
As locals and real estate partners, we guide clients through every step of Hamptons living — seasonal rentals, long-term stays, purchases, sales, and all the little transitions in between. With deep knowledge of the area and a genuine love for this community, we’re here to help you take the next step, whether you’re discovering the Hamptons for the first time or have been coming here for years.
