HAMPTONS
Homes & Seasons YOUR POCKET GUIDE TO FALL ON THE EAST END
TABLE CONTENTS Of RHYTHMN OF FALL
08
APPLE PICKING
10
IMMERSE YOURSELF IN THE SLOWER SIDE OF THE HAMPTONS
BEST ORCHARDS & PUMPKIN PATCHES
FALL BOUNTY
12
BREWERIES AND VINEYARDS
20
THANKSGIVING OUT EAST
22
MUST VISIT FARMS, MARKETS, & RESTAURANTS
THE BEST PLACES TO SIP SLOWLY AND ENJOY AUTUMN HARVESTS
HOSTING TIPS & RITUALS
ESSENTIAL TIPS FOR AUTUMN THE BASICS OF FALL OUT EAST
26
FROM JENNA’S
desk
WELCOME TO FALL IN THE HAMPTONS 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.
Jenna
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,
Joe
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.
05
THE EAST END COMES ALIVE EACH OCTOBER WITH ICONIC CELEBRATIONS & SMALL-TOWN CHARM Life moves slower now. Many shops and restaurants
This is the rhythm of fall on the East End —
it’s wise to check ahead before you go. But there’s
about savoring the little things: a shopkeeper’s
reduce their hours or close altogether midweek, so 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.
slower, more spacious, quietly enchanting. It’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.
EVENTS & FESTIVALS
where fall comes ALIVE
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.
THE EAST END COMES ALIVE EACH OCTOBER WITH ICONIC CELEBRATIONS & SMALL-TOWN CHARM Out east in Montauk, autumn takes on its own flavor with the Montauk Fall Festival. The village green
Just down the road in Sag Harbor, the
chowder compete for top honors, local vendors line
with kids (and even pets) marching proudly
buzzes with small-town energy as steaming bowls of
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.
Ragamuffin Parade brings a whimsical twist, 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
At Hank’s PumpkinTown in Water Mill, the
in autumn — low and golden, casting a
atmosphere is as lively as it gets — children
makes even the simplest outing feel like a
hard cider, and everyone ends up with
glow across the fields and orchards — that 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.
race through the corn maze, parents sip on more pumpkins than they meant to bring home. It’s one of those places where fall feels big and joyful, a true destination.
For something a little more serene, Seven
It’s the picture-perfect fall outing, complete with cider
where you can wander at your own pace.
photographers chase all season long.
Ponds Orchard offers rows of apple trees
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. Over 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.
donuts
and
the
kind
of
golden-hour
light
that
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 and fall BOUNTY Fall
in
the
abundance.
Hamptons
The
means
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 late-summer tomatoes, holding on until the first
frost. It’s the season when meals practically roasted
write
squash
themselves:
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.
And at the very end of fall, when the light fades
In Amagansett, Amber Waves celebrates fall with
squash, and hearty vegetables that find their
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,
vibrant vegetables, fresh bread, and seasonal
way onto holiday tables across the East End.
rare gift on the East End, carrying the community
For us, stopping at the farm stands isn’t just
pantry goods.
the car with mums & pumpkins from Balsam, the
flowers. Their farm stand stays open year-round, a through the quietest months with local staples and
shopping — it’s a ritual. Every October we load unofficial kickoff to our family’s holiday season.
FLAVORS OF FALL
out east
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 a certain 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.
Il Buco al Mare in Amagansett is made for exactly
this stretch of fall. On a good night, the floor-toceiling windows are thrown open, locals and visitors
are stacked around the bar and spilling onto the sidewalk, and the smell of fresh focaccia carries out
into the street. I've genuinely never had a bad meal
there, and that consistency is what keeps us coming back.
For something a little more tucked away, Lucky's in East Hampton has that small, cozy tavern feel, hearty
steaks, martinis shaken tableside, and a pace built for
lingering. It's the place for friends, a long table, and no reason to rush home.
One of our favorite rituals is stealing away for a fall
date night: a quiet table at Il Buco al Mare or settling into Lucky's for steaks and martinis by candlelight.
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.
SIP SOMETHING CRISP WHILE SOAKING UP THE FALL LIGHT
For something a little different,
Their seasonal beers are playful
starters
and unexpected, often released in limited runs that make them
Westhampton Beach Brew & Grille on Main makes a great
fall stop. It's the rare Hamptons brewery with a full food menu to match the beer, think stacked burgers, wings, and shareable
place
sweater weather in a glass —
gone. It’s the kind of spot where
spiced
feel
you can tuck into a cozy corner
seasonal without being heavy.
with friends, sampling pours that
The taproom itself has that laid-
feel like a little discovery.
longer.
outside with the sea breeze is
For something truly tied to the
Some
one of those small pleasures that
harvest,
to
back surf-town vibe, and sipping
rotating
On a cool afternoon, it's an easy
worth seeking out before they’re
enough
a
lineup of their own craft brews.
Their pumpkin ale tastes like just
alongside
to
land
after
a
day
outside: settle in, order a pint and something off the grill, and let the afternoon stretch a little
of
our
favorite
fall
weekends are the ones where we
makes a day trip east feel
Cider
offers a crisp, apple-forward
complete.
option made right on the farm.
for a beach walk and a pumpkin
Back in Sag Harbor, Kidd Squid Brewing Co. brings a quirky, small-batch approach.
Hank’s
Hard
It’s a grown-up way to extend an afternoon of pumpkin picking — the taste of the orchard in your glass.
follow the leaves out to Montauk ale, or over to Westhampton Beach for a pint and a full meal at Brew & Grille on Main to close out the day.
VINEYARDS
for slow AFTERNOONS
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
For a fuller escape, consider a day trip to the North
Then there’s Channing Daughters, a smaller, locally
can sip and gaze out across the Sound as the day
run place that feels like stumbling on a secret. It’s more low-key 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.
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 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.
THANKSGIVING
on the East End
By late November, the Hamptons has settled fully
Days are shorter, but somehow that makes every
stand nearly bare against pale skies, and the ocean
the bay become a daily ritual, and cozy evenings at
into its quiet season. The air turns crisp, the trees
takes on that steel-blue hue that signals winter’s approach.
sunny afternoon feel more precious. Long walks by home take center stage.
Without the summer rush, everything moves at a
It’s also the season of gathering—around long tables,
linger a little longer at the farm stands, shopkeepers
warm in hand. Thanksgiving in the Hamptons isn’t just
gentler pace—there’s room to breathe again. Locals 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.
by crackling fires, or simply with a mug of something 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
Thanksgiving morning is best spent outside. Bundle up
here is how easy it is to create a feast without doing
for a turkey trot through town or a peaceful walk by
incredible turkey — juicy, flavorful, and totally
more earned, and it’s one of those little local
it all yourself. Smokin’ Wolf BBQ makes an
the bay — it’s a ritual that makes the meal feel even
stress-free — so you can spend your day hosting, not
traditions that never loses its charm.
fashioned desserts people talk about all year. Their
Whether you’re cooking every dish from scratch or
basting. Fairview Farm’s pies are the kind of old-
crust tastes just like my grandmother’s: flaky, buttery, and perfectly nostalgic.
Round Swamp Farm stays open late into the season, stocked with prepared sides, specialty
goods, and fresh local ingredients. The farm stands still
overflowing
Hamptons has a way of feeling timeless. It’s the mix of farmstand abundance, salty air, and small-town
IT’S A MOMENT BETWEEN SEASONS THAT FEELS BOTH CALM AND FULL OF ANTICIPATION
are
leaning on local favorites, Thanksgiving in the
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.
warmth that makes the holiday here truly special.
There's a version of East Hampton summer
that lives mostly in imagination: the pool at dusk, the ping pong game that runs too late, the outdoor shower after a beach day. At 29 Blue Jay Way, it's just Tuesday.
SOME HOUSES GIVE YOU A PLACE TO STAY. THIS ONE GIVES YOU A REASON TO STAY OUTSIDE. Set back and private just minutes from the
Village, this newly refreshed retreat was clearly designed by people who understood
the assignment: light-filled rooms that don't try
to compete with what's happening outside, and a backyard that's become the whole point.
A heated saltwater pool, an oversized spa,
and enough patio to never sit in the same spot twice. Downstairs, a finished lower level with a
media room and wine cellar means the party has somewhere to go when the sun does set.
Four bedrooms and three renovated baths give everyone their own space, but the real
value here is the address: minutes from the
Racquet Club, the Village, Sag Harbor, and
Wainscott, with nowhere you need to be except back by the pool. Inquire for details.
IMAGES HAVE BEEN DIGITALLY MODIFIED USING AI; ORIGINAL PHOTOGRAPHS ARE AVAILABLE UPON REQUEST
joseph.vanasco@elliman.com jenna.vanasco@elliman.com
ESSENTIAL TIPS AUTUMN for
MUST-HAVES FOR YOUR HAMPTONS ADVENTURE
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.
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.
01
02
03
SWEATERS & SALT AIR
BOOTS MADE FOR CRUNCHING
BLANKET FOR GOLDEN HOUR
Bring layers you can throw on for
From pumpkin patches to village
Keep one in the car for sunset on
breezy vineyard terrace.
every step more fun.
house is always the beach.
a windswept beach walk or a
04
sidewalks,
sturdy
boots
make
the sand — the best seat in the
05
MARKET TOTE
MUG FOR WARM SIPS
06
Farm stands brim with squash,
Hot cider, coffee, or tea feels
The coastal light in fall is pure
you packed a roomy bag.
wander Main Street.
capturing off your phone.
mums, and pies — you’ll be glad
07
better in your hands while you
CAMERA OR POLAROID magic — soft, golden, and worth
08
09
Plan a stop at a vineyard or
Villages are quieter midweek —
Fall in The Hamptons is about
cozy once the crowds are gone.
cafés with no rush. Note changes
SIP & STROLL brewery — tastings feel extra
WEEKDAY WANDERINGS
pop into shops, galleries, and in weekly hours.
SLOW DOWN SEASIDE
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. And for homeowners who split their time here, we help manage the property in between, so it's cared for and ready whenever you are.
Whether you're just starting to explore, you've been coming here for years, or you need a trusted partner to care for your home while you're away, 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. From our family to yours,
Jenna & Joe
JENNA-JOE.COM