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It sounds almost like the beginning of a fairy tale: nestled in a crowded street by the sea is a quaint little shop filled with hidden treasures. 

Down the Rabbit Hole Wine Boutique is very real, and its story, while not exactly a fairy tale, is a personal journey for owner Jessica Green. The Mattituck native is the third proprietor of the tiny Sayville wine store, which under her ownership was named one of Wine Mag’s Top 50 Wine Retailers of 2021.

“The whole idea of going down the rabbit hole is finding something different,” said Green.

The store — which is a little larger than a posh walk-in closet — now sells exclusively natural, organic and sustainable wines.

“I want to support smaller vineyards from all over the world and everyone is a little bit more health conscious, not only with what we’re doing to the environment, but people don’t realize what gets put in wine,” she said.

Green got her start in the industry working at the former Diliberto Winery in Jamesport (now Terra Vite) in 2007. She was the first employee at the winery and was working to pay for her first year of college at LIU-Brooklyn, where she was studying to be a physician’s assistant before switching to nursing.

The work was hard, with Green assisting owner Sal Diliberto on everything from harvesting to bottling, but she ended up staying there for 12 years. 

“I had no idea how good she would be,” Diliberto said. “She came in and learned fast. As soon as she turned 21 and started tasting wines, I saw some real potential.”

Diliberto encouraged Green to formally study wine. She took courses with the Sommelier Society of America, the American Sommelier Association and the Culinary Institute of America (CIA). She admits that shifting from being a nurse to studying wine full-time was daunting, especially because her family is made up largely of health care workers.

“I thought I was going to get disowned,” Green joked. 

Down the Rabbit Hole Wine Boutique in Sayville. (Credit: Courtesy photo)

Of course her family has been very supportive.

“Being naive, I thought she was just going to be tasting wine!” said Green’s mother, Judy Hubbard. “How are you going to live? I didn’t realize the education behind it. But I’m so proud of her.”

While Green has left the North Fork for Sayville, her roots here run deep. Her grandparents, the late Thelma and Herman Hubbard, were lifelong North Forkers, with Herman familiar to multiple generations of Mattituck residents as a custodian at Mattituck High School for 37 years.

Down the Rabbit Hole has been a labor of love for Green. During the pandemic, her tiny business actually thrived, as she hand-delivered wine to her clientele.

“That’s what made the shop notable,” she said. “I was able to meet my customers face-to-face.”

Green started a successful wine club and also found a sizable, loyal customer base in city residents who stop in Sayville to board the Fire Island Ferry.

The wines on offer include bottles from all over the world and rotate seasonally. On the shelves, you’ll find wine from Australia, Chile, Long Island and even South Africa. All of the wines are sustainable and most are natural. In addition to the store, Green owns and operates Wine Vie LLC, hosting wine tasting classes and restaurant consulting, which has been a big success.

“Natural wines have an elegance, a beautiful balance,” Green said. “They have all the complexities in what you’re used to drinking. That’s what I push here. Decent, delicious wines.”