Ask an Agent: Prime Spots for Apple and Pumpkin Picking, Corn Mazes, and More Fall Fun in the Hamptons and North Fork
by Grace Cassidy
October 2025
Fall is in full swing across the northeastern U.S., with crisp temperatures, crunchy leaves, and all your favorite autumnal activities. To help you find the best spots to pick your own apples and pumpkins, explore corn mazes, and enjoy some fall fun in the Hamptons and North Fork of Long Island, we asked Douglas Elliman agents who live and work in those communities to recommend their favorite destinations.
The Hamptons
Hank’s Pumpkintown, Water Mill, NY
Hank’s is a favorite among locals and visitors alike for its apple and pumpkin picking, family-friendly fall activities, and their incredible market with treats, pies, doughnuts, roasted corn, and apple cider. They’ve also got a corn maze and gem mining, which the kids will love.
“Hanks is a great destination spot,” says Westhampton-based agent Kimberly Cammarata. “They have great candy apples. I volunteered there one year, and the people that work there are phenomenal. They really care about their clientele. And they always keep it fresh—there’s always something new every year.”
Fairview Farm at Mecox, Bridgehampton, NY
Head down to Fairview Farm at Mecox for fresh produce, herbs, cut flowers, and U-Pick pumpkin, gourds, and squash. Stop by the farmstand for culinary quality fresh local goods, and make sure to grab some pies for dessert. Kids love the 8-acre corn maze, which is designed in a different theme every year.
Milk Pail, Water Mill, NY
The Milk Pail is an iconic Hamptons spot for delicious fresh-picked apples, pumpkins, gourds, and squash. After picking apples from their orchard, stop by the market for fresh produce, baked goods, honey, eggs, and much more. This is also a great spot to get a floral arrangement by Amy’s Flowers, either designed yourself or with help from their experts.
The North Fork
The Waterdrinker, Manorville, NY
The Waterdrinker is the place to go for pumpkin picking, sunflowers, weekend hay rides, barnyard animals, and more. The fall season welcomes a haunted corn maze, food trucks, and their Fall Festival and Mum Mania.
“They have a brewery on-site, games, all the animals, things for kids to climb on—it’s amazing,” Cammarata says. “This is where I recommend.”
They also have a Riverhead location on Sound Avenue, open Wednesday through Sunday.
Harbes Family Farm, Mattituck, NY
Harbes is a local favorite for all-things fall. In operation for over 35 years, the farm has multiple sites for family fun, including their main location in Mattituck (which includes their barnyard adventure, farmstand, and vineyard), as well as an orchard in Riverhead and a farm in Jamesport. Stop by for apple and pumpkin picking, hay rides, festivals, events, and much more.
Woodside Orchards, Aquebogue, NY
Woodside Orchards, which has locations in both Aquebogue and Jamesport, has been family owned and operated since 1982, starting as an apple orchard with fresh fruit and baked goods to buy. Today, they offer U-Pick apples at both locations, and a tasting room in Aquebogue, where they serve hard and non-alcoholic ciders.
“Woodside Orchards is really fun,” says Cutchogue-based agent Melissa Principi, who also serves as the Vice President of the Mattituck Chamber of Commerce. “The grounds are well manicured, and the trees are beautiful.”
Krupski Farms, Peconic, NY
Krupski Farms offers a generous farmstand with lots of fresh produce and U-Pick pumpkins during the fall season.
“Krupski Farms is a gem,” Principi says. “It’s small, but their haunted barn and tractor rides are so fun. It’s perfect for the whole family and has a low-key charm.”
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