Homes & Seasons
FROM JENNA’S desk
WELCOME TO THE VERY FIRST EDITION OF HAMPTONS HOMES & SEASONS
Lately, I’ve been craving the simple rhythms of life days where the pace feels slower, moments stretch a little longer, and the focus is on being present instead of plugged in This summer, we tried to give our kids as much of that as we could: playing outside until the light faded, riding bikes through the neighborhood, and even snapping Polaroids so I could capture memories without being tethered to my phone Maybe it’s because I leaned hard into content creation and felt the edges of burnout, or maybe it’s the constant hum of the news cycle but I’ve found myself wanting to step back into a more intentional way of living
Around the same time, I stumbled into a little fascination: reading old postcards from the Hamptons on eBay I’d pore over the messages and study the faded photographs of familiar spaces the Hook Mill windmill, Town Pond, even the little one-room schoolhouse Eventually I bought one postcard from 1955, sent home from camp The message was simple, but the handwriting stopped me It was in looping cursive, the kind that instantly reminded me of my grandmother’s letters, even though it must have been a child’s. There’s something about holding that card knowing it traveled across time, carrying both a place and a moment that made me think about how we document life here today
I’ve wanted to create a comprehensive, seasonal guidebook for a long while, and this felt like the right moment to begin My hope is that something in these pages inspires you to try a new ritual, visit a favorite spot, or maybe even to write a postcard of your own Pull out a pen, practice your cursive, and share a memory or a sentiment with someone you love
Fall in the Hamptons is one of the most magical times of year If you ’ ve found yourself here this season count yourself lucky
a note from joe
October has arrived, and with it comes that unmistakable crispness in the air It’s finally time to pull the flannels, vests, and boots out of the closet my favorite time of year. The pace slows just enough that conversations last a little longer and mornings stretch quietly It feels like even the leaves take their time falling after a fast-paced summer.
This season always brings reflection Once again, we’ve had a record-breaking year more rentals, more sales, and, most importantly, more connections with people discovering what makes this place so special It looks like we’ll hold the #1 rental spot in the Hamptons for the second year running, and we’re still busy helping customers find their perfect fall and offseason escapes.
Outside of real estate, I’ve been carving out time to write and record music from my cozy home studio. The cooler weather means it’s back to bike rides to Montauk and Sag Harbor, surf sessions without the crowds, and lingering at local festivals with family and friends pumpkins, apples, and all.
We hope this edition of our guide helps you experience the Hamptons the way we do with curiosity, gratitude, and a deep love for this community.
Warmly,
EVENTS & FESTIVALS ALIVE where fall comes
The Wölffer Estate Harvest Party is one of the most iconic fall traditions in the Hamptons a joyful celebration that brings together locals, weekenders, and visitors for a true taste of vineyard life at its peak Held each October at Wölffer Estate in Sagaponack, the day-long event feels like stepping into a golden postcard: long tables set between the vines, crisp autumn air filled with live music, and glasses of rosé and reds flowing freely Families spread out on picnic blankets, children join in grape-stomping competitions, and friends gather around platters of seasonal food from local purveyors It’s part wine festival, part community picnic, and entirely about savoring the beauty of harvest season in the Hamptons.
Out east in Montauk, autumn takes on its own flavor with the Montauk Fall Festival The village green buzzes with small-town energy as steaming bowls of chowder compete for top honors, local vendors line the walkways, and live music carries on the breeze Bundle up in a sweater, wrap your hands around a hot cider, and wander the tents this is Montauk at its most charming, the kind of weekend that feels both festive and familiar
The season also brings one of the East End’s marquee cultural events: the Hamptons International Film Festival (HIFF) For one long weekend in October, red-carpet glamour meets small-town intimacy as acclaimed films and emerging voices are screened in local theaters. From East Hampton to Sag Harbor, audiences mingle with directors, actors, and industry insiders Whether you ’ re catching an Oscar contender or discovering a hidden gem, HIFF is where the world comes to the Hamptons and the Hamptons shine right back
And of course, no East End autumn is complete without Halloween East Hampton Village transforms on October 31st as Main Street fills with children in costume, shopkeepers handing out candy, and families gathered on the sidewalks for a safe, oldfashioned celebration
THE EAST END COMES ALIVE EACH OCTOBER WITH ICONIC CELEBRATIONS & SMALL-TOWN CHARM
Just down the road in Sag Harbor, the Ragamuffin Parade brings a whimsical twist, with kids (and even pets) marching proudly down Main Street in costume, cheered on by neighbors and friends These traditions capture the true spirit of fall here festive, familyfriendly, and steeped in community charm
APPLE PICKING and golden afternoons
There’s something about the Hamptons light in autumn low and golden, casting a glow across the fields and orchards that makes even the simplest outing feel like a memory you’ll keep forever
Fall weekends on the East End often begin in the orchards. Families pile into the car, baskets in hand, ready for a day of apple picking and pumpkin hunting
At Hank’s PumpkinTown in Water Mill, the atmosphere is as lively as it gets children race through the corn maze, parents sip on hard cider, and everyone ends up with more pumpkins than they meant to bring home It’s the kind of place where fall feels big and joyful, a true destination.
For something a little more serene, Seven Ponds Orchard offers rows of apple trees where you can wander at your own pace Alongside the crisp apples, visitors can cut their own sunflowers a burst of color against the fading greens and yellows of the fields
This orchard is especially close to our hearts: ten years ago, right in the middle of the pumpkin patch, Joe proposed A decade later, it still feels like the most magical corner of the East End to us proof that these farms aren’t just about produce, but about the stories and memories families carry home.
THESE FARMS AREN’T JUST ABOUT PRODUCE, BUT ABOUT THE STORIES AND MEMORIES
FAMILIES CARRY HOME.
And then there’s the Milk Pail in Water Mill, a Hamptons classic Tractor rides through the orchards, bags of apples weighed down with Honeycrisps and Galas, pumpkins stacked in every size and color
It’s the picture-perfect fall outing, complete with cider donuts and the kind of golden-hour light that photographers chase all season long
Whether you ’ re chasing adventure with the kids or a slow, scenic afternoon, apple picking on the East End is as much about the light and the landscape as it is about what you carry home Golden afternoons in the orchards are fall in the Hamptons at its very best
FARMS BOUNTY and fall
Fall in the Hamptons means abundance. The farm stands practically spill over this time of year bins of delicata, acorn, and butternut squash stacked beside sugar pumpkins, pale gourds, and even the last of the latesummer tomatoes, holding on until the first frost It’s the season when meals practically write themselves: roasted squash soups, pumpkin breads, hearty salads with the final bursts of Sungolds
At Balsam Farms, the tables groan with fall bounty, but what’s most impressive is what happens behind the scenes Balsam cans and preserves so much of their produce, capturing the season so it can be enjoyed long after the harvest ends Shelves line with jars of tomatoes, pickles, and sauces a reminder of just how rich these fields are
FARM STANDS & MARKETS OVERFLOW WITH SQUASH, PUMPKINS, AND THE SMALL-TOWN RITUALS THAT MARK THE END OF THE SEASON.
In Amagansett, Amber Waves celebrates fall with vibrant vegetables, fresh bread, and seasonal flowers Their farm stand stays open year-round, a rare gift on the East End, carrying the community through the quietest months with local staples and pantry goods
And at the very end of fall, when the light fades before five, Amber Waves hosts one of the sweetest small-town traditions: children decorate lanterns and walk through the fields to “put them to sleep” for the winter The glow of the lanterns in the early dusk is a memory for children and adults alike proof that farms here are about community as much as produce
Halsey Farm in Water Mill rounds out the season with a Southampton classic: corn, squash, and hearty vegetables that find their way onto holiday tables across the East End
For us, stopping at the farm stands isn’t just shopping it’s a ritual Every October we load the car with mums & pumpkins from Balsam, the unofficial kickoff to our family’s holiday season
out east FLAVORS OF FALL
Fall in the Hamptons is all about atmosphere, and the restaurants that shine this time of year are the ones that make you want to linger long after dessert In Sag Harbor, Tutto Il Giorno glows with candlelight, serving soulful Italian dishes that feel made for sweater weather Just a ferry ride away on Shelter Island, Léon 1909 captures the soul of fall dining on the East End Linger by the open hearth with seasonal dishes and the kind of warmth that makes even a chilly fall evening feel timeless.
Out in Montauk, Gurney’s proves that the beach isn’t just for summer Their fire pits overlooking the Atlantic are reason enough to stop by, especially with a glass of wine or a hot cocktail in hand as the waves crash below And in East Hampton, Nick & Toni’s remains a classic its wood-fired oven and rustic dining room make it the kind of place where locals gather all season long
THE EAST END DINING SCENE DOESN’T SLOW DOWN WHEN SUMMER ENDS. IT JUST
GETS COZIER.
For something heartier, The Bell & Anchor in Sag Harbor serves seafood and seasonal comfort dishes with a waterfront view It’s a reminder that fall on the East End isn’t just about cozy sweaters and foliage it’s about flavors that feel rooted in the season.
Highway Restaurant & Bar (East Hampton) is a true year-round favorite, but it feels especially inviting in the fall The menu is seasonal and thoughtful think roasted vegetables, hearty pastas, and cocktails that hit the right balance of classic and creative It’s the kind of place where locals settle into a leather banquette on a chilly night, knowing they’ll be just as happy with a burger as they would be with a more refined special Highway has that understated Hamptons charm: no flash, just consistently excellent food in a setting that feels warm and familiar
One of our favorite rituals is stealing away for a fall date night a quiet table at Tutto or cocktails by the fire pit with live music at Baron’s Cove. After the rush of summer, these moments feel like a deep breath.
BREWERIES CIDER and
Montauk Brewing Company
Autumn on the East End pairs perfectly with a pint. Local breweries and cideries capture the season in ways that feel both casual and celebratory a chance to sip something crisp while soaking in the fall light
In Montauk, Montauk Brewing Co. is always worth the drive Their pumpkin ale tastes like sweater weather in a glass spiced just enough to feel seasonal without being heavy The taproom itself has that laidback surf-town vibe, and sipping outside with the sea breeze is one of those small pleasures that makes a day trip east feel complete
Back in Sag Harbor, Kidd Squid Brewing Co. brings a quirky, small-batch approach
SIP SOMETHING CRISP WHILE SOAKING UP THE FALL LIGHT
Their seasonal beers are playful and unexpected, often released in limited runs that make them worth seeking out before they’re gone It’s the kind of spot where you can tuck into a cozy corner with friends, sampling pours that feel like a little discovery
For something truly tied to the harvest, Hank’s Hard Cider offers a crisp, apple-forward option made right on the farm It’s a grown-up way to extend an afternoon of pumpkin picking the taste of the orchard in your glass
And for those who don’t mind crossing the bay, Greenport Harbor Brewing Co. makes a North Fork detour worthwhile Their waterfront taproom pairs perfectly with a golden-hour drive, the kind where the leaves are glowing and the air feels sharp and clean Ordering a seasonal ale here feels like a punctuation mark on a fall day trip the reward after a meandering afternoon on the back roads
Some of our favorite fall weekends are the ones where we follow the leaves out to Montauk for a beach walk and a pumpkin ale, or across the bay to Greenport for a day that ends with a pint as the sun sets over the harbor
VINEYARDS AFTERNOONS for slow
Vineyards are among the East End’s most magical fall spots where the vines glow at sunset, the air smells of damp earth and fermenting grapes, and the tasting rooms pull you in with wood beams, fireplaces, or lawn chairs spread out under turning leaves
At Wölffer Estate in Sagaponack, fall feels especially luxurious Their awardwinning reds are reason enough to visit, but what really seals the moment is live music on the terrace as the sun dips low, wine glasses clinking, and the vineyard bathed in soft amber light Reservations are strongly recommended seated table service with vineyard views becomes one of those evenings you’ll want on repeat
FROM SAGAPONACK TO GREENPORT, THE HAMPTONS & NORTH FORK ARE WOVEN
TOGETHER BY WINE
Then there’s Channing Daughters, a smaller, locally run place that feels like stumbling on a secret It’s more lowkey than grandeur bring a blanket, sit on the lawn with your wine flight, or cozy up inside their tasting room if the air gets crisp There’s a warmth here that’s unpressured: tasting wines, watching the sky shift, being with friends without clocks.
For a fuller escape, consider a day trip to the North Fork There are around 50+ wineries scattered across this stretch of Long Island all driveable, many with tasting rooms, and dozens of picturesque countryside views and quonset barns along the way
Two favorites of ours there are Bedell Cellars in Cutchogue, which delivers reds that feel polished and evocative, and Kontokosta Winery in Greenport, perched right on the water, a relaxing stop where you can sip and gaze out across the Sound as the day wanes
Whether you ’ re savoring a glass at golden hour in Sagaponack or day-tripping to the North Fork’s quieter roads, fall is the season when wine country feels its most magical The crowds have thinned, the vines glow with autumn light, and every tasting feels like an invitation to slow down.
THE RHYTHM of fall
When autumn settles over the Hamptons, the energy shifts. The hum of summer traffic disappears, replaced by the crunch of leaves underfoot and the steady rhythm of tides rolling onto empty beaches It’s a season that belongs to those who linger the visitors and locals who know the real magic begins after Labor Day
Life moves slower now Many shops and restaurants reduce their hours or close altogether midweek, so it’s wise to check ahead before you go But there’s something grounding in that simplicity. A coffee shop open only on weekends, a farm stand closing at dusk the quiet feels intentional, reminding you to match your pace to the season
At Duck Pond in East Hampton, the trees flame with color, their reflection turning the water into a painter’s canvas It’s the kind of spot where you find yourself staying longer than planned, just watching the light shift A short drive away, Main Beach or Ditch Plains offer that same sense of stillness, only with salt air and waves for company Off-season, the shoreline becomes yours to wander
Places like LongHouse Reserve and the Madoo Conservancy also take on a new personality in the fall Without the bustle of summer visitors, you can hear the crunch of gravel paths, notice how sculpture casts long shadows across the grass, or lose yourself in gardens tinged with gold The art and the landscapes feel more personal, as if they were waiting for you alone
THE EAST END COMES ALIVE EACH OCTOBER WITH ICONIC CELEBRATIONS & SMALL-TOWN CHARM
This is the rhythm of fall on the East End slower, more spacious, quietly enchanting It’s about savoring the little things: a shopkeeper’s wave, a farmstand bouquet of late-season dahlias, the last glow of sunlight on the water before night comes early In this season, you don’t just visit the Hamptons you live in step with it
THANKSGIVING on the East End
By late November, the Hamptons has settled fully into its quiet season The air turns crisp, the trees stand nearly bare against pale skies, and the ocean takes on that steel-blue hue that signals winter’s approach
Without the summer rush, everything moves at a gentler pace there’s room to breathe again Locals linger a little longer at the farm stands, shopkeepers greet you by name, and favorite restaurants take a well-deserved pause midweek. It’s a moment between seasons that feels both calm and full of anticipation
There’s a softness to the villages this time of year Twinkling lights begin to appear in shop windows, wreaths are hung on picket fences, and the scent of woodsmoke drifts through the air
Days are shorter, but somehow that makes every sunny afternoon feel more precious Long walks by the bay become a daily ritual, and cozy evenings at home take center stage.
It’s also the season of gathering around long tables, by crackling fires, or simply with a mug of something warm in hand Thanksgiving in the Hamptons isn’t just about the feast; it’s about savoring the rhythm of late fall, surrounded by people and places that feel timeless It’s a reminder that sometimes the most meaningful moments come when life slows down and the simple pleasures take center stage.
One of the best parts of spending Thanksgiving out here is how easy it is to create a feast without doing it all yourself Smokin’ Wolf BBQ makes an incredible turkey juicy, flavorful, and totally stress-free so you can spend your day hosting, not basting Fairview Farm’ s pies are the kind of oldfashioned desserts people talk about all year Their crust tastes just like my grandmother’s: flaky, buttery, and perfectly nostalgic
IT’S A MOMENT BETWEEN SEASONS THAT FEELS BOTH CALM AND FULL OF ANTICIPATION
Round Swamp Farm stays open late into the season, stocked with prepared sides, specialty goods, and fresh local ingredients. The farm stands are still overflowing with late-season squash, Brussels sprouts, kale, and herbs everything you need to bring a little East End abundance to your table For entertaining, Cavaniola’s Gourmet is a dream Their cheeses, charcuterie, and specialty finds make it easy to build a grazing board that looks stunning with almost no effort
Thanksgiving morning is best spent outside Bundle up for a turkey trot through town or a peaceful walk by the bay it’s a ritual that makes the meal feel even more earned, and it’s one of those little local traditions that never loses its charm
Whether you ’ re cooking every dish from scratch or leaning on local favorites, Thanksgiving in the Hamptons has a way of feeling timeless. It’s the mix of farmstand abundance, salty air, and small-town warmth that makes the holiday here truly special
Tucked in the heart of East Hampton, this beautifully designed home blends timeless coastal charm with effortless functionality Light-filled living spaces, curated interiors, and inviting outdoor areas make it perfect for year-round living or seasonal escapes.
THE MAGIC OF THE HAMPTONS ISN’T JUST IN THE HOUSES- IT’S THE LIFE YOU
From here, everything you love about the Hamptons is just moments away beaches, farm stands, village dining, and endless natural beauty
Whether you ’ re dreaming of a weekend getaway or your next full-time residence, this home captures the best of East End living
Inquire for details.
joseph vanasco@elliman com jenna.vanasco@elliman.com
ESSENTIAL TIPS AUTUMN for
Fall on the East End is a season of contrasts: golden afternoons that still feel like summer, followed by crisp evenings that call for a sweater and a glass of red It’s when the beaches are wide open, farm stands overflow with pumpkins, and the light turns everything it touches into a postcard
Packing for a Hamptons fall isn’t about overthinking it’s about being ready to chase the little rituals that make this season so special. A blanket for sunset, boots for crunching through leaves, and maybe a tote bag for those spur-of-the-moment farm stand stops
MUST-HAVES FOR YOUR HAMPTONS ADVENTURE
Most of all, fall here is about slowing down Stroll the villages without a rush, linger over coffee, or watch the sky shift pink over the water These are the simple coastal luxuries that turn an ordinary weekend into a memory
SWEATERS & SALT AIR
Bring layers you can throw on for a windswept beach walk or a breezy vineyard terrace
BOOTS MADE FOR CRUNCHING
From pumpkin patches to village sidewalks, sturdy boots make every step more fun
BLANKET FOR GOLDEN HOUR
Keep one in the car for sunset on the sand the best seat in the house is always the beach
MARKET TOTE SIP &
Farm stands brim with squash, mums, and pies you’ll be glad you packed a roomy bag
STROLL
Plan a stop at a vineyard or brewery tastings feel extra cozy once the crowds are gone
Hot cider, coffee, or tea feels better in your hands while you wander Main Street
MUG FOR WARM SIPS WEEKDAY WANDERINGS
Villages are quieter midweek pop into shops, galleries, and cafés with no rush Note changes in weekly hours.
CAMERA OR POLAROID
The coastal light in fall is pure magic soft, golden, and worth capturing off your phone
SLOW DOWN SEASIDE
Fall in The Hamptons is about pace-- long walks, salty air, and unhurried moments
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 fits their life best. Maybe it’s a summer rental that becomes a cherished annual tradition. Maybe it’s the first home where new memories will unfold. Or maybe it’s the right time to sell and start a new chapter.
As longtime locals and real estate partners, we guide clients through every stage from seasonal rentals and vacation homes to sales and purchases with deep knowledge of the area and a genuine love for this community Whether you ’ re just starting to explore or you ’ ve been coming here for years, we’d love to help you write your next Hamptons chapter.
JENNA-JOE.COM
joseph.vanasco@elliman.com 631-353-1043
jenna vanasco@elliman com 717-333-5449
UNTIL NEXT SEASON...
Thank you for wandering through the magic of fall on the East End with us. Every season out here has its own rhythm, but autumn will always hold something special — a quieter pace, golden light, and the simple rituals that make life feel a little more beautiful.
Whether you ’ re near or far, we hope these pages inspire you to savor the season, share a postcard (or two), and make your own Hamptons memories.
With love from our family to yours, Jenna & Joe
