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Hamptons.com
September 26, 2025

Top Hamptons Hot Spots for Apple Picking, Pumpkin Picking, and Family Fun!

Veronica Chumbiby Veronica Chumbi
in Community, Trending
Home Community

Fall officially back! But early birds get the worm—or, in this case, pick out the best pumpkins. Sweater weather is approaching, and the scent of pumpkin spice lattes is lingering in the air.

 

Hamptons.com has curated a list of the best places for fun fall activities! Whether you enjoy getting lost in the corn maze, want to pick the perfect apples, or want to enjoy a hayride, we’ve got you covered.

 

Hank’s Pumpkin Town

240 Montauk Hwy, Water Mill, NY
Monday through Sunday – 9:30am – 5:30pm

This is a gem in the Hamptons! Enjoy apple picking, pumpkin picking, a Maze Park full of fun activities for kids, shop at the market for fresh apple cider and their famous apple cider donuts!

Their Famous Corn Maze is pictured above, can find your way through? 


 Fairview Farm at Mecox

19 Horsemill Ln, Bridgehampton, NY 11932
Friday through Sunday – 10:00am – 6:00pm

Have you ever shot a corncob out of a cannon? Well, you can, here! If you hit the target, you’ll win a gourd! Answer the questions to get through their stunning maze, enjoy delicious ribbon fries cooked right in front of you, and pick out a pumpkin for carving that perfect Halloween ghoul.


Corwith Farmstand

851 Head of Pond Rd, Water Mill, NY 11976
Mondays through Sunday – 9:00am – 5:00pm

Pet and feed the cutest baby goats! They are very friendly and waiting for you to stop by and say hello. Meet their animal friends, two lazy pigs and an energetic sheep. Kids will love exploring the playground and being surrounded by farm animals. On your way out purchase delicious apple pies, corn and pumpkins.


Milk Pail U-Pick Farm

50 Horsemill Ln, Water Mill, NY 11976
Friday through Sunday – 10:00am – 5:30pm

They have a variety of apples for you to pick! Empire, Gala, Golden Delicious, Honeycrisp, Macoun to name a few. They also have Pumpkin picking and Sunflower picking! There’s a beautiful field of sunflowers you can cut and enjoy – you’ll want to take out your camera for this one!


Seven Ponds Orchard

65 Seven Ponds Road, Watermill, NY 11968
Mondays through Sunday – 9:00am – 6:00pm

Enjoy hayrides, a corn maze, a huge playground and a market full of fresh seasonal fruit, baked goods and seasonal vegetables.

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LOCAL EVENTS

Events

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Aperitivo (Sunset Cocktails)

October 9 @ 05:00 PM - October 9 @ 08:00 PM
The Baker House 1650
09
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09
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Emilio Moro Wine Dinner at R.AIRE

October 9 @ 06:30 PM - October 9 @ 08:30 PM
259 East Montauk Hwy, Hampton Bays, NY, 11946
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R.AIRE Wine Dinner with Emilio Moro

October 9 @ 06:30 PM - October 9 @ 09:30 PM
259 E Montauk Hwy, Hampton Bays, NY 11946
09
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“The First Science from the Vera Rubin Observatory” (A Free, Virtual Lecture)

October 9 @ 07:00 PM - October 9 @ 08:00 PM
Hamptons Observatory with Suffolk County Community College (online)
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The Sag Harbor American Music Festival Complete Line-Up Revealed

Top Hamptons Events This Weekend: September 26th, 2025

  • The 33rd Hamptons International Film Festival kicked off last Friday with the U.S. premiere of A24’s Eternity starring Elizabeth Olsen, Miles Teller, and Callum Turner.⁠
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Elizabeth Olsen attended the premiere on Friday, and on Saturday sat down with IndieWire’s Editorial Director Kate Erbland at the Sag Harbor Cinema as a part of the festival’s “A Conversation With” series. Later that day, the second “A Conversation With” took place as Ethan Hawke and moderator Alison Stewart talked about Blue Moon, as well as Hawke’s filmography. ⁠
⁠
Sydney Sweeney received the festival’s Achievement in Acting Award following the U.S. premiere of her film Christy in East Hampton. ⁠
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Notable Guests included: Alessandro Nivola, Alec Baldwin, Amanda Peet, Tonatiuh, Miriam Shor, Lois Smith, Tim Blake Nelson, Mareille Enos, Bob Balaban, E. Jean Carroll, Roberta Kaplan, Ellen Barkin, Bernie Telsie, Bill Condon.⁠
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📸: Jess Dalene⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#hiff #hamptonsinternationalfilmfestival #film #elizabetholsen #sydneysweeney #hamptons #hamptonsfilm⁠
  • When: Fri, Oct 3rd – Sun, Oct 5th, 2025
8am – 5pm

Where: Levain Bakery, 354 Montauk Hwy, Wainscott, NY

Levain Bakery is introducing a new cookie for a limited time: Peanut Butter Dark Chocolate Chip – a decadent mix of creamy and chunky peanut butter with rich dark chocolate chunks. Originally created to celebrate the opening of Levain’s Beverly Hills Bakery, this indulgent new flavor will now be available for just three days only, October 3–5, at all retail bakery locations.

To make the weekend even sweeter, guests who purchase a cookie will receive a Levain Bakery mini tote (while supplies last), a fan-favorite collectible sure to go quickly.

#levain #levainbakery #cookie #minitote #tote #hamptons
  • From world premieres at the Hamptons International Film Festival to SouthamptonFest! ⁠
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Check out the Top Hamptons Events This Weekend!⁠
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🎬 33rd Hamptons International Film Festival⁠
📅 Oct 3 – 13, 2025 | 9AM – 10PM⁠
📍 Various Locations⁠
A global lineup of films, shorts & documentaries.⁠
⁠
🍪 Levain Bakery⁠
📅 Oct 3 – 5, 2025 | 8AM – 5PM⁠
📍 354 Montauk Hwy, Wainscott⁠
Try the Peanut Butter Dark Chocolate Chip cookie + snag a mini tote (while supplies last).⁠
⁠
🎉 13th Annual SouthamptonFest⁠
📅 Oct 3 – 5, 2025 | 10AM – 7PM⁠
📍 Southampton Village⁠
Arts, culture, food & family fun all weekend long!⁠
⁠
🎶 SpringsFest⁠
📅 Oct 4, 2025⁠
📍 1 Parsons Pl, East Hampton⁠
Live music, raffles, crafts, blacksmith demos & more.⁠
⁠
💃 Salsa Social @ The Clubhouse Hamptons⁠
📅 Oct 4, 2025 | 9PM – 11:30PM⁠
📍 East Hampton⁠
Dance the night away w/ DJ Chile & more!⁠
⁠
🐚 34th Annual Largest Clam Contest⁠
📅 Oct 5, 2025 | 12PM – 3PM⁠
📍 Amagansett Life Saving Station⁠
Taste clam chowder, clam pies & cheer on the winners!⁠
⁠
🎷 East Meets West Jazz Jam Session⁠
📅 Oct 5, 2025 | 2PM – 5PM⁠
📍 Southampton Cultural Center⁠
Free community jazz jam – all are welcome.⁠
⁠
🌕 Full Hunter’s Super Moon Hike⁠
📅 Oct 6, 2025 | 6:30PM – 7:30PM⁠
📍 SOFO Museum Parking Lot⁠
Guided evening hike under the moonlight.⁠
⁠
✨ Which event are you most excited for?⁠
⁠
Check out more events at Hamptons.com (Link in Bio)⁠
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#hamptons #hamptonsinternationalfilfestival #hiff #jazz #fullmoon #hike #film #levainbakery #community
  • So many fun fall activities in the Hamptons 🎃

@fairviewfarmatmecox 
@corwithsfarmstand 
@milkpailfarmorchard 

Check out our fall guide at Hamptons.com (Link in Bio)

#hamptons #fall #applepicking🍎 #pumpkin #maze #pettingfarm
  • As summer winds down and the cool breezes of fall approach, jewelry enthusiasts and fashion lovers alike are looking for the latest seasonal trends. Yael Fraynd, founder and president of Yaya Publicity, offers an insider’s perspective on what to expect this fall — especially for those embracing the chic lifestyle of the Hamptons.⁠
⁠
Looking ahead to fall, Fraynd described the evolving styles with enthusiasm. For fall, expect to see bold statement pieces, rich gemstone colors like orange and a playful mix of metals. ⁠
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She also noted the influence of pop culture on jewelry trends, including celebrities like Taylor Swift, who is recently engaged, saying, “It could also be just, you know, with Taylor Swift, who has such a big effect on what people like.”⁠
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On the seamless transition from summer to fall styles, she observed, “In the summer, you see a bit of Western-inspired pieces, and I think that they really do kind of transition into fall really nicely. ⁠
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@yayapublicity⁠
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Read the full article at Hamptons.com (Link in Bio) ⁠
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#fall #falltrend #falljewelry #hamptons⁠
  • Apollo in the Hamptons returned with a celebratory evening at the EHP Resort & Marina (Si Si Restaurant) in East Hampton. The annual fundraiser supported Apollo’s year-round artistic and educational programs and its first full-scale renovation and restoration. ⁠
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📸: Danté Crichlow for The Apollo⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#apollo #apollotheater #hamptons #easthampton #benefit #fundraiser
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