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Kristen Hand of Sherwood House Vineyards. (Credit: Barbaraellen Koch)

Kristen Hand is a former waitress and longtime nanny who knows a thing or two about staying on her toes.

Perhaps that’s why the 28-year-old has adapted so quickly to being tasting room manager at Sherwood House Vineyards in Jamesport, a position she’s held for the past 18 months.

A Deer Park native who now lives in Coram, Hand was at a professional crossroads when she discovered the Main Road winery while hanging out with friends in spring 2013.

“I didn’t even know it was here initially,” she said.

The day of her visit, she struck up a conversation with Sherwood House bartender Paul Helbig and told him that she’d graduated from Hunter College in New York City with the intention of becoming a physician’s assistant but no longer felt it was the right fit for her.

“And Paul handed me [Sherwood House] co-owner Brian Skip’s card,” she said. “I emailed him that night.”

Soon enough, Hand had secured the job as tasting room manager — and had no choice but to dive right in.

“They put me behind the bar right away and it was really overwhelming. I was wearing white!” she said with a laugh. “I didn’t think I was going to be working with wine that day.”

Recently, we sat down with Hand to talk about learning from Sherwood House winemaker Gilles Martin, knowing most of her customers by name and the difficulty of making everyone feel like they’re the most important person in the room.

Q: How do you keep customers happy when there’s a bar full of people waiting to be served?

A: Our patrons are a small, tight-knit group of people. We have a lot of locals and I know a very strong percentage of my customers by their first name. I know their mothers’ names; I know their children’s names. I also kind of treat Sherwood like my own house, so I feel like I’m entertaining people in my home and try to provide that same vibe. If you have a little bit of wine in your glass, you have no problems. 

Q: What do you like most about your job?

A: I love our staff. We’re kind of like an odd, dysfunctional family living on the Island of Misfit Toys. We’ve all become very good friends with each other. But I also really enjoy learning about the wine and spending time with Gilles, our winemaker. He’s been pretty influential for me. I think without him even realizing it, he’s become kind of a natural mentor to me. He’s a natural teacher and I’m a natural student, so we gel nicely. 

Q: What’s the most challenging aspect of managing a tasting room?

A: Since I treat Sherwood like my home, sometimes it’s hard to always be “on.” It’s like having company at my house every day. But that’s when I really lean on my staff, especially on weekends. That’s when I really appreciate them more than any other time. 

Q: What’s your favorite wine at Sherwood House, and why?

A: Currently it’s our 2010 Blanc de Blancs. We only put out a sparkling every few years and this one is just really special. I like the dryness of it. It kind of has these doughy characteristics and I love bubbles.

Q: If you could tell prospective winery visitors one thing, what would it be?

A: Pack your favorite snack and do a little tasting, figure out what you like and just sit back and enjoy.

This story originally appeared in the 2015 spring edition of The Long Island Wine Press.