Autumn in the Hamptons carries its own kind of magic. As the summer crowds fade and the crisp air rolls in off the Atlantic, the East End reveals a more intimate, low-key side of its legendary luxury lifestyle. The beaches are quieter, the farm stands overflow with pumpkins and apples, and the event calendar takes on a distinctly festive, family-friendly feel (with plenty of grown-up options, too). For those who know, fall is when the Hamptons feel most like home.
From harvest parties to haunted villages, contemporary art to indie cinema, fall 2025 boasts experiences that reflect the region's luxurious yet local charm. Below, we spotlight the can't-miss events that define the season—and a few marquee moments beyond the Hamptons that still belong on your calendar.
725 Art Show
September 27–October 13, 2025
Whaling & Historical Museum, Sag Harbor
The beloved 725 Art Show returns to a storied Sag Harbor venue: the Whaling and Historical Museum. The show features an impressive roster of East End artists across a variety of media—painting, sculpture, photography, and mixed media. The atmosphere is both high-art and highly local, perfect for collectors and casual observers alike. With proceeds supporting the museum, it's a wonderful way to experience the area's cultural heritage while connecting with its creative present.
Whaling & Historical Museum, Sag Harbor
The beloved 725 Art Show returns to a storied Sag Harbor venue: the Whaling and Historical Museum. The show features an impressive roster of East End artists across a variety of media—painting, sculpture, photography, and mixed media. The atmosphere is both high-art and highly local, perfect for collectors and casual observers alike. With proceeds supporting the museum, it's a wonderful way to experience the area's cultural heritage while connecting with its creative present.
Springsfest
October 12–13, 2025
Springs, East Hampton
In the heart of Springs, one of East Hampton's most artistic hamlets, Springsfest captures the soul of the season. Think: live music, craft vendors, local eats, hayrides, and kid-friendly activities—all hosted outdoors under the golden canopy of autumn leaves. Now in its second year, Springsfest is quickly becoming a go-to fall tradition for families, creatives, and anyone who loves small-town warmth with big Hamptons flavor.
Springs, East Hampton
In the heart of Springs, one of East Hampton's most artistic hamlets, Springsfest captures the soul of the season. Think: live music, craft vendors, local eats, hayrides, and kid-friendly activities—all hosted outdoors under the golden canopy of autumn leaves. Now in its second year, Springsfest is quickly becoming a go-to fall tradition for families, creatives, and anyone who loves small-town warmth with big Hamptons flavor.
Hank's Pumpkintown
Open Daily Through Halloween
Water Mill, Southampton
No fall in the Hamptons is complete without a trip to Hank's. With pumpkin patches, apple picking, corn mazes, wagon rides, cider donuts, and a family-friendly farm stand experience, Hank's Pumpkintown in Water Mill embodies the spirit of the season. While geared toward families with children, the nostalgic charm and photogenic setting draw in visitors of all ages. Go early to beat the crowds—and leave with a car full of fall bounty.
Water Mill, Southampton
No fall in the Hamptons is complete without a trip to Hank's. With pumpkin patches, apple picking, corn mazes, wagon rides, cider donuts, and a family-friendly farm stand experience, Hank's Pumpkintown in Water Mill embodies the spirit of the season. While geared toward families with children, the nostalgic charm and photogenic setting draw in visitors of all ages. Go early to beat the crowds—and leave with a car full of fall bounty.
2025 Hamptons International Film Festival
October 3–13, 2025
Various locations
Celebrating its 33rd year, the Hamptons International Film Festival (HIFF) remains one of the most prestigious cultural events on the East Coast. With screenings held in East Hampton, Southampton, Sag Harbor, and Montauk, this star-studded festival highlights emerging talent, international auteurs, and Oscar-bound features. It's as much a scene as it is a cinema showcase, with panels, parties, and special screenings making it a must-attend for creatives, cinephiles, and socialites alike.
Various locations
Celebrating its 33rd year, the Hamptons International Film Festival (HIFF) remains one of the most prestigious cultural events on the East Coast. With screenings held in East Hampton, Southampton, Sag Harbor, and Montauk, this star-studded festival highlights emerging talent, international auteurs, and Oscar-bound features. It's as much a scene as it is a cinema showcase, with panels, parties, and special screenings making it a must-attend for creatives, cinephiles, and socialites alike.
Wölffer Estate Annual Harvest Party
October 11, 2025
Sagaponack
Set among the vines of one of the East End's premier vineyards, the Wölffer Estate Harvest Party in Sagaponack is an elevated yet delightfully relaxed afternoon of wine tasting, live music, artisanal food, and lawn games. Expect a casually elegant crowd, plenty of Wölffer rosé and cider, and the kind of golden-hour glow that defines a perfect Hamptons autumn day.
Sagaponack
Set among the vines of one of the East End's premier vineyards, the Wölffer Estate Harvest Party in Sagaponack is an elevated yet delightfully relaxed afternoon of wine tasting, live music, artisanal food, and lawn games. Expect a casually elegant crowd, plenty of Wölffer rosé and cider, and the kind of golden-hour glow that defines a perfect Hamptons autumn day.
Montauk's 44th Annual Fall Festival
October 11, 2025
Montauk Town Green
Head east to the end of the island for Montauk's most beloved fall tradition. Hosted by the Montauk Chamber of Commerce, this three-day celebration includes a chowder contest, craft vendors, kids' games, and live music on the Town Green. With the ocean as your backdrop and the village decked in autumn colors, it's an iconic way to enjoy the season—and a good excuse to book a long weekend at Gurney's or Marram.
Montauk Town Green
Head east to the end of the island for Montauk's most beloved fall tradition. Hosted by the Montauk Chamber of Commerce, this three-day celebration includes a chowder contest, craft vendors, kids' games, and live music on the Town Green. With the ocean as your backdrop and the village decked in autumn colors, it's an iconic way to enjoy the season—and a good excuse to book a long weekend at Gurney's or Marram.
Haunted Village
October 25, 2025
Southampton History Museum
For a spooky twist on local history, the Southampton History Museum transforms its grounds into a haunted village, complete with costumed characters, ghost stories, and eerie installations. This all-ages experience offers just the right dose of fright, nestled in one of the region's most historic settings.
Southampton History Museum
For a spooky twist on local history, the Southampton History Museum transforms its grounds into a haunted village, complete with costumed characters, ghost stories, and eerie installations. This all-ages experience offers just the right dose of fright, nestled in one of the region's most historic settings.
Spooky Silent Disco
October 25, 2025
Guild Hall, East Hampton
Costumes, cocktails, and curated playlists come together at Guild Hall's Halloween Silent Disco Dance Party. Held in the outdoor garden under twinkling lights, this modern twist on a masquerade ball invites guests to choose their channel, find their beat, and dance the night away—headphones on, spirits high. It's one of the more whimsical and stylish events on the late-October calendar.
Guild Hall, East Hampton
Costumes, cocktails, and curated playlists come together at Guild Hall's Halloween Silent Disco Dance Party. Held in the outdoor garden under twinkling lights, this modern twist on a masquerade ball invites guests to choose their channel, find their beat, and dance the night away—headphones on, spirits high. It's one of the more whimsical and stylish events on the late-October calendar.
Long Island Restaurant Week
November 3–9, 2025
Multiple Locations
Food lovers rejoice. Long Island Restaurant Week brings prix-fixe menus to some of the East End's most coveted dining destinations. Whether you're indulging in a seasonal tasting menu at Arthur and Sons NY Italian in Bridgehampton or indulging at The Palm East Hampton at the historic Huntting Inn, it's a chance to explore new spots—or revisit favorites—without the summertime demand. Reservations are a must.
Multiple Locations
Food lovers rejoice. Long Island Restaurant Week brings prix-fixe menus to some of the East End's most coveted dining destinations. Whether you're indulging in a seasonal tasting menu at Arthur and Sons NY Italian in Bridgehampton or indulging at The Palm East Hampton at the historic Huntting Inn, it's a chance to explore new spots—or revisit favorites—without the summertime demand. Reservations are a must.
Beyond the Hamptons: Two Fall Events Worth the Drive
The beauty of life in the Hamptons is that you're never too far from the liveliness of Long Island's western burgs. For those seeking see-and-be-seen events beyond the Hamptons' elevated offerings, there are two events in particular you won't want to miss this fall, including the world's most famous international golf competition.
The Ryder Cup
September 23–28, 2025
Bethpage Black, Farmingdale
On its own, the Ryder Cup is a seminal event for both die-hard golfers and those with only a passing interest. Put this tension-filled biennial event at the always raucous Bethpage Black golf course, and you have Long Island's biggest signature event in some time. Expect international crowds, elevated hospitality experiences, and world-class golf—all less than 90 minutes west of the Hamptons. For those with access to private transfers, this is a must-attend fall outing.
Bethpage Black, Farmingdale
On its own, the Ryder Cup is a seminal event for both die-hard golfers and those with only a passing interest. Put this tension-filled biennial event at the always raucous Bethpage Black golf course, and you have Long Island's biggest signature event in some time. Expect international crowds, elevated hospitality experiences, and world-class golf—all less than 90 minutes west of the Hamptons. For those with access to private transfers, this is a must-attend fall outing.
Oyster Fest
October 19–20, 2025
Downtown Oyster Bay
Just to the north of Farmingdale, a few weeks after the Ryder Cup matches come to a close, the largest waterfront festival on the East Coast commences with the Oyster Fest in Downtown Oyster Bay. Drawing thousands for two days of seafood, entertainment, and maritime flair, the festival features a number of popular activities, including live music and entertainment, an arts and crafts pavilion, oyster shucking and eating contests, chef demos, and plenty of outstanding seafood.
Downtown Oyster Bay
Just to the north of Farmingdale, a few weeks after the Ryder Cup matches come to a close, the largest waterfront festival on the East Coast commences with the Oyster Fest in Downtown Oyster Bay. Drawing thousands for two days of seafood, entertainment, and maritime flair, the festival features a number of popular activities, including live music and entertainment, an arts and crafts pavilion, oyster shucking and eating contests, chef demos, and plenty of outstanding seafood.
Discover More of The Hamptons High End Coastal Lifestyle
Fall in the Hamptons is an invitation to indulge and explore the region's "off-peak" seasonal wonders. Whether you're browsing contemporary art in Sag Harbor, sipping wine in Sagaponack, or dancing beneath the stars in East Hampton, the season offers a quieter, more curated version of luxury. And for those lucky enough to call the Hamptons home, these fall events serve to enhance an already unparalleled lifestyle further.
If you're interested in learning more about this extraordinary, sought-after coastal destination, including information on luxury Hamptons real estate—or if you’re considering a sale—contact The Agency Hamptons today and allow our extensive expertise and commitment to our clients to help guide your Hamptons real estate journey.
