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At Milk Pail in Water Mill, 12th-generation farmers balance modern and manageable

By Arielle Dollinger | November 8, 2023 | published on

As apples redden and pumpkins ripen, you-pickers flock to Milk Pail, owned by 12th-generation farmers. As residents of a three-bedroom, three-bathroom house on the Water Mill property, which borders Mecox Bay, the family takes a two-pronged approach to security: a fence keeps the deer away, and security personnel patrol the perimeter on golf carts.

“I really like where I live,” said one of the family members, Jennifer Dupree. “And it’s much easier to run a farm when you’re living at it.”

Three households live on the farm: Jennifer, 48, her husband, Craig Dupree, 49, and two children, Jennifer’s parents, and Jennifer’s sister and brother-in-law. The parking lot for the you-pick section is halfway across the farm, separate from the area the houses occupy.

Most of the estimated 500 to 1,000 people who visit the 60-acre property on an autumn Saturday buy the one-size-only bag to pick apples, and treat the owners with respect.

“Most people get it,” said Jennifer Dupree. “The biggest thing where they don’t understand private versus public is, they come and they just want to walk around … which usually entails taste-testing the apples.”

Once, Dupree looked out an upstairs window in her mother’s house to see apples flying over the treetops.

“So I holler out the window, I’m like, ‘There’s no throwing apples here,'” she said. “And they’re like, ‘Who’s that?!’ ”

Life on her family’s farm has “its ups and its downs,” she said. While the revenue generated by you-pick apples and pumpkins does not make or break the business, the autumn season is the busiest. The farm is open for you-pick on weekends only.

“The one major difference with our you-pick and most of the others,” she said, is “we’re not into the agri-entertainment. It makes a ton of money, but it’s like a crazy headache.”

Instead, Milk Pail continues to sell produce, baked goods and gift items at the Milk Pail Fresh Market on Montauk Highway and the Milk Pail Farm Stand on Mecox Road.

“The only issue that we’ve come up against on the South Fork,” Dupree said, is “the property value is extremely high, and the property taxes, therefore, are extremely high.”

But her passion for farming has kept her from considering selling the land, and the taxes have not priced the family out of farming yet, she said.

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