Who says the Hamptons are only a summer destination?
As the final weeks of October unfold, the East End offers plenty of reasons to get out and enjoy the season. From intimate dinners and vineyard celebrations to live music, festive parades, and community fundraisers, the Hamptons’ autumn calendar is anything but quiet.
With the summer crowds long gone and the villages settling into a more relaxed rhythm, this time of year offers a chance to experience another side of the Hamptons. Whether you’re a year-round resident or planning a fall weekend Out East, here are some events worth adding to your calendar before October comes to a close.
R.AIRE Murder Mystery Dinner
October 23 | 6 PM | The Hampton Maid, Hampton Bays
An evening of fine dining comes with an unexpected twist at R.AIRE, the acclaimed restaurant at The Hampton Maid. On October 23, guests are invited to step back into the 1930s for an immersive murder mystery experience, complete with intriguing characters, hidden clues, and a crime waiting to be solved.
The evening begins with a welcome cocktail, followed by a three-course dinner during which the mystery unfolds around the table. Guests are encouraged to dress in their finest 1930s-inspired attire and put their detective skills to the test before the culprit is revealed.
For those looking to trade an ordinary dinner reservation for something a little more memorable, this theatrical dining experience offers a particularly entertaining way to spend a fall evening.
Little Lucy’s Annual Halloween Pet Parade
October 24 | 1 PM | Agawam Park, Southampton
One of Southampton’s most charming Halloween traditions returns on October 24, inviting local pets and their owners to show off their most creative costumes.
Little Lucy’s Annual Halloween Pet Parade brings together animal lovers for an afternoon of festive fun, with costumed companions parading through Southampton Village. The celebration also supports local animal welfare organizations, giving participants an opportunity to contribute to a worthy cause while enjoying the festivities.
Whether you’re dressing up your own four-legged friend or simply stopping by to admire the costumes, it’s a lighthearted community gathering that has become a seasonal favorite.
Wölffer Cider Fest
October 24 | 2–5 PM | Wölffer Wine Stand, Sagaponack
Few places capture the beauty of an East End autumn quite like Wölffer Estate. On October 24, the vineyard’s Wine Stand hosts Cider Fest, an afternoon dedicated to seasonal flavors, music, and outdoor fun.
Guests can enjoy Wölffer’s locally produced ciders alongside live entertainment, games, and food from the LUNCH Lobster Roll truck. With activities for younger visitors as well, the gathering offers an inviting way for families and friends to spend a crisp October afternoon.
Against the backdrop of Sagaponack’s picturesque vineyards, it’s a fitting celebration of the harvest season and one of the many pleasures of spending fall Out East.
New York State Whiskey Celebration
October 24 | 3–7 PM | Sagaponack Farm Distillery
The East End’s agricultural heritage takes center stage at Sagaponack Farm Distillery’s New York State Whiskey Celebration, an afternoon highlighting locally crafted spirits, food, and live entertainment.
The event brings together Sagaponack Farm Distillery and guest producers, including Twisted Cow Distillery and Kidd Squid Brewing Co., with barbecue from Townline BBQ and live music by Chris Kline.
Set at the Sagaponack distillery, the gathering offers visitors an opportunity to discover regional producers and experience the growing craft beverage scene on the East End. It’s an especially appealing outing for those interested in local agriculture, artisanal production, and the businesses helping shape the area’s food and drink culture.
First Annual Sag Harbor Supper Stroll
October 24 | 4–7 PM | Sag Harbor Village
Sag Harbor’s celebrated dining scene takes on a community-minded twist with the inaugural Supper Stroll, a progressive dining experience benefiting the Sag Harbor Food Pantry.
Participants are invited to explore the village on foot, stopping at eight participating restaurants to sample signature dishes along the way. The evening brings together some of Sag Harbor’s favorite culinary destinations, offering a chance to discover local flavors while supporting an organization that provides essential assistance to neighbors in need.
With stops including village restaurants and an opportunity to enjoy drinks and dessert along the route, the event combines good food, a walkable downtown, and a meaningful cause.
For anyone who enjoys exploring Sag Harbor’s independent restaurants, it’s a particularly rewarding way to spend an October evening.
Yoga in the Pavilion at Canoe Place
October 25 | 9:30–10:30 AM | Canoe Place, Hampton Bays
For a slower start to the weekend, Canoe Place offers a peaceful Sunday morning experience with its complimentary yoga sessions led by instructors from Doza Yoga.
Held in the property’s Pavilion, the all-levels class invites participants to enjoy a mindful hour of movement, stretching, and relaxation in one of Hampton Bays’ most distinctive historic settings.
Whether you’re an experienced yogi or simply looking to begin your Sunday with a little movement, the session offers a welcome opportunity to recharge. Participants are encouraged to bring their own mats and water.
Sag Harbor Ragamuffin Parade
October 25 | 1–2:30 PM | Sag Harbor Village
Halloween spirit takes over Sag Harbor Village on October 25 as the annual Ragamuffin Parade brings costumed children, families, and pets together for one of the community’s most beloved fall traditions.
The festive procession travels through the village, with participants showing off everything from classic Halloween costumes to imaginative homemade creations. The celebration continues near the Sag Harbor Whaling Museum and Custom House, where families can enjoy an afternoon carnival.
More than just a Halloween celebration, the parade reflects the close-knit character of Sag Harbor and the longstanding local traditions that bring residents together year after year.
Autumn Acoustics in the Garden at Canoe Place
October 21 & 28 | 5–8 PM | Canoe Place, Hampton Bays
There’s something especially appealing about spending an autumn evening outdoors, and Canoe Place makes the most of the season with its Autumn Acoustics in the Garden series.
Held on Wednesday evenings through October 28, the gatherings feature intimate live acoustic performances in the property’s garden, where glowing firepits create a cozy atmosphere as the sun sets.
Guests can settle in with seasonal bites and cocktails while enjoying music beneath the stars. Whether meeting friends after work or planning a relaxed midweek outing, the series offers an inviting way to experience the quieter side of the Hamptons.
Wölffer After Dark: Halloween Party
October 30 | 7–10 PM | Wölffer Estate, Sagaponack
As Halloween approaches, Wölffer Estate trades its relaxed vineyard afternoons for a more spirited evening celebration.
Wölffer After Dark invites guests to enjoy a Halloween party featuring specialty cocktails, wine, beer, light bites, and music from a DJ. Costumes are encouraged, with prizes awarded for the evening’s best looks.
The event offers a festive opportunity to experience the vineyard after sunset, bringing together Wölffer’s signature hospitality and a lively Halloween atmosphere.
For those planning a night out with friends, it’s a stylish way to celebrate the holiday in the heart of Sagaponack.
Halloween Eve at Green Room Hamptons
October 30 | 11 PM | Green Room Hamptons, Hampton Bays
For those looking to keep the Halloween festivities going into the night, Green Room Hamptons is hosting a late-night celebration on October 30.
The Halloween Eve party invites guests to dress up and enjoy an evening of dancing, music, and festive drinks in the heart of Hampton Bays.
With a lively atmosphere and plenty of opportunities to show off a creative costume, the event offers a fun alternative to the area’s more traditional seasonal gatherings.
More Halloween Festivities Around the East End
October 30–31 | Various Locations
The final weekend of October brings even more opportunities to celebrate, particularly in Sag Harbor, where local cultural institutions are joining forces for a weekend of Halloween-themed programming.
Spooky-Palooza, a collaboration between The Church, Sag Harbor Cinema, and Bay Street Theater, features costume celebrations, film screenings, and theatrical entertainment. The festivities include a Halloween dance party, family-friendly programming, and screenings of seasonal favorites.
Meanwhile, Sag Harbor’s annual Pumpkin Trail brings trick-or-treating to Main Street on October 31, with participating local businesses welcoming costumed children for an afternoon of Halloween fun.
Together, these events highlight the creativity, community spirit, and local traditions that continue to make the East End an engaging destination well beyond summer.
A Season Worth Staying For
The Hamptons may be synonymous with long beach days and bustling summer weekends, but autumn reveals a different kind of charm. As the pace slows, there’s more time to appreciate the local restaurants, cultural institutions, independent businesses, and community traditions that give the East End its distinctive character.
Leave a Reply