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Down The Rabbit Hole: New York's Smallest Wine Shop Sits On Main Street In Sayville

SAYVILLE, N.Y. (CBSNewYork) –  Sayville, Long Island is home to the smallest wine shop in New York state—a narrow 100 square feet of retail space built into an alleyway on Main Street, tucked between a spice shop and a chocolatier.

"It's a very intimate setting, which I love," sommelier and owner Jessica Green said.

Newcomers are surprised to find such a tiny operation.

"They're like, 'Wait. Is this it? Is there more?' I'm like, 'Nope. You're in the rabbit hole. This is it,'" she said.

She took over Down the Rabbit Hole Wine Boutique from its original proprietor in 2019, inheriting the shop's Alice in Wonderland-themed decor.

"I wouldn't dare to change it," she said. "When you think Alice in Wonderland, you think 'fun.' You think 'different.' You think, 'What am I trying?' or 'What am I going to turn around and find?'"

She takes pride in offering the rare and unexpected.

"We have herbal, earthy wines. We have more fruit-forward wines. We have wines with a little bit of spice," she said.

She relies on years of experience working at vineyards and in restaurants, rotating her seasonal collection of mostly organic, sustainable, and biodynamic bottles.

"I almost feel like they're my babies walking out. I'm like, 'Okay. You're going to a good home,'" she said.

She happily welcomes and encourages first-time wine drinkers, explaining when their purchases should be slightly chilled or allowed time to open up.

"It's almost like giving instructions to a babysitter," she said.

Eager to share her knowledge, she's also grateful for the opportunity to learn from her Sayville customers, many of whom she has come to call her friends.

"It's definitely building a tiny little community in this little store and talking about wine," she said. "It brings people together. Wine's always done that."

Down the Rabbit Hole Wine Boutique
4 Main Street
Sayville, NY 11782
(631) 589-9463

What's something few people know about but everybody should? Whatever it is, Elle McLogan is tracking it down on The Dig. Join her hunt for treasures hidden across our area. Follow Elle on Twitter and Instagram.

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