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Hamptons.com
September 26, 2025

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

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Veronica Chumbiby Veronica Chumbi
in Community, Trending
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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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The quaint, charming, and walkable town of Westhampton Beach offers a shopping scene that blends coastal style with curated sophistication. Along Main Street and its surrounding pockets, you’ll find a mix of locally owned boutiques, specialty shops, and go-to stops that reflect the relaxed yet elevated feel of the Hamptons.

Best Boutiques & Shops in Westhampton Beach

The quaint, charming, and walkable town of Westhampton Beach offers a shopping scene that blends coastal style with curated sophistication. Along Main Street and its surrounding pockets, you’ll find a mix of locally owned boutiques, specialty shops, and go-to stops that reflect the relaxed yet elevated feel of the Hamptons.

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Chez Adriana Castro is Totally at Home in the Hamptons

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Top Hamptons Events This Weekend: September 26th, 2025

  • Looking to shop local in Montauk? Visit the Montauk Farmers Market on the Montauk Village Green every Thursday from 9am - 2pm and explore fresh produce, flowers, baked treats, and more from 40+ local vendors.

#Montauk #Hamptons
  • For the third summer in a row, Dolce & Gabbana returns to Gurney’s Montauk Resort with its signature seasonal storefront. Inspired by Italian design and set against Montauk’s picturesque coastline, it’s a standout destination for fashion lovers this summer.
#Hamptons 
@dolcegabbana
  • Sant Ambroeus has become one of the East End’s most beloved dining destinations. The place has style, serves gelato and espresso all day, offers inviting outdoor seating, and delivers a world-class dining experience.

Their fresh pasta is made with eggs, and doesn’t weigh you down like other pasta does. The signature branzino dish has become a calling card for the Southampton location.

No visit is complete without a stop at the gelato counter, where handcrafted gelato and sorbetto are churned in-house, offering a cool, classic finish to a summer meal.

You’ll see me there again sipping an espresso and pretending to be Italian. Diet starts tomorrow.
  • Ralph’s Coffee is popping up at Mulford Farm for the summer season. Stop by from 8am - 5pm for specialty drinks, pastries, outdoor seating, and lawn games until September 7th.
@ralphscoffee 
#Popup #ralphscoffee #coffee
  • Today, @childrensmuseumoftheeastend hosted its 16th Annual Family Fair in Bridgehampton, raising funds for its on-site food pantry, providing summer camp scholarships to local children, and supporting other initiatives that serve East End families year-round.

A special thank you to CMEE and lead event sponsor Saunders & Associates for welcoming us to capture the day’s magic.
  • We stopped by Pre-Loved in Montauk to see where founder @sunnymelet sources her vintage pieces. You can visit Pre-Loved any day of the week from 10am - 6pm.
@prelovedmtk
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