Fall in Love with the Hamptons: Uncovering Autumn’s Best-Kept Secrets Out East
As summer fades and the vibrant fall colors take center stage, the Hamptons transform into a postcard-worthy escape. Crisp beach walks, cozy sweaters, and the smell of hot cider fill the air, making autumn the perfect time to explore these charming villages. Whether you're a local or a visitor, the Hamptons offers an array of festivals and activities that capture the essence of fall. Let's dive into the Staymarquis' guide of the best Fall events and activities the Hamptons has on offer!
Amber Waves Oktoberfest Fundraiser
Kick off the season with the Amber Waves Oktoberfest Fundraiser, a can't-miss event for families and fall lovers alike. The fundraiser promises a day filled with live music, farm feasts, and friendly races for both kids and adults. Bring your coziest blanket, indulge in farm-fresh food, and know that your ticket supports a great cause.
- Date: October 20th (Rain date: October 21st)
- Location: Amber Waves Farm, Amagansett
- Details: Pre-sale ticket link above. $200 at the door, no refunds due to it being a fundraiser
Montauk Fall Festival
For over 40 years, the Montauk Fall Festival has been a staple of the autumn season. The two-day event features pumpkin carving, a Clam Chowder Contest, local vendors, and family-friendly activities like crab racing and inflatable obstacle courses.
- Date: October 7-8
- Location: Montauk Village Green
- Highlights: Raffle prizes, live music, and a farmer's market with local treats
Savor the Hamptons' Wine Country
Fall is the perfect time to sip your way through the Hamptons' renowned vineyards. With over 60 wineries in the region, you'll find a mix of rich fall flavors paired with scenic views.
Wölffer Estate
This Sagaponack favorite hosts an annual Harvest Party featuring grape-stomping, local wines, and kid-friendly fun. Don't miss their Sunset Saturdays, where you can enjoy live music, wine by the glass, and the beauty of an autumn sunset.
Channing Daughters Winery
For a more intimate experience, head to Bridgehampton for an autumn tasting. With small batches of handcrafted wines, Channing Daughters offers bold flavors and fewer crowds.
Duck Walk Vineyards
Water Mill's Duck Walk Vineyards invites you to sip their famous Blueberry Port while enjoying live music and a serene outdoor setting.
Pumpkin Patches, Apple Orchards, & Corn Mazes
No fall season is complete without a visit to the pumpkin patch or a crisp afternoon spent apple picking. The Hamptons boast some of the best fall farms on Long Island.
Hank's Pumpkintown
Explore pumpkin patches, corn mazes, and enjoy hayrides at this family-friendly hotspot in Water Mill.
The Milk Pail
Pick your own apples and pumpkins, browse fresh produce, and savor homemade goods at The Milk Pail's Fresh Market.
Woodside Orchards
This family-owned orchard in Aquebogue offers fresh apple picking, cider tastings, and delicious apple cider doughnuts.
Halloween Happenings
The Hamptons come alive with Halloween spirit, offering something for everyone—from spooky to sweet:
Southampton History Museum
Become a paranormal investigator and explore the haunted grounds of Rogers Mansion. If you dare, walk through the Haunted Village and see if you can survive until the end!
Little Lucy's Halloween Pet Parade
Southampton's beloved pet parade features costumed pups, live music, and treats for your furry friends, all while supporting the Kent Animal Shelter.
Gurney's Halloween Hideaway
Head to Montauk for family-friendly Halloween fun, including candle-making workshops, tarot card readings, and trick-or-treating around the resort.
Outdoor Adventures
Fall is the perfect season to get outside and explore the natural beauty of the Hamptons.
Hike Shadmoor State Park
With cooler weather, now's the time to lace up your sneakers and hit the trails.
Practically Private Beaches
“Second Summer” (i.e. Fall) offers the perfect opportunity for peaceful beach days, with mild weather and fewer crowds. Pack a blanket and savor a quiet, off-season moment by the shore.
Cozy Fall Dining Experiences
Fall is a time to slow down and enjoy seasonal flavors in the Hamptons' best restaurants.
Léon 1909
Located on Shelter Island, Léon serves up rustic, Provençal-style dishes with seasonal ingredients. The scallop crudo and handmade pastas are a must-try.
Elaia Estiatorio
Experience a taste of Greece at this Bridgehampton gem, where you can enjoy locally sourced, Mediterranean-inspired dishes in a cozy autumn setting.
Montauk Brewing Co.
Sip on Montauk Brewing Company's seasonal pumpkin ale, crafted with traditional brewing methods and high-quality ingredients.
Seasonal Festivals & Performances
From film festivals to art exhibits, fall is also the season to embrace culture in the Hamptons.
Hamptons International Film Festival
Running from October 7-16, this renowned film festival showcases award-winning films in an intimate setting.
Parrish Art Museum
Visit the Parrish Art Museum for an inspiring day of art and culture, with exhibits like Joaquín Sorolla and Esteban Vicente: In the Light of the Garden on display through mid-October.
Fall in the Hamptons is a magical season filled with rich traditions, seasonal flavors, and unforgettable moments. Whether you're exploring vineyards, picking apples, or taking in a sunset by the shore, the Hamptons has something for everyone to enjoy this autumn. Ready to make the Hamptons your home away from home? Contact us today to find your perfect luxury vacation rental!