Dorothy Vaccaro

Dorothy Vaccaro is the General Manager of Boxwood Estate Winery in Middleburg, Virginia.  She has been working there since 2017. Dorothy describes herself as a big supporter of local small businesses, especially retail, eating, and drinking establishments. She “loves finding hidden gems: whether it’s a good dive bar, an independent bookstore, or the Secret Sidewalk in Rochester, NY.”  

Dorothy is also an avid animal lover, adding, “I am a particularly proud Cat Lady.”

More about Dorothy:  (**Please listen to  my conversation with Dorothy on the podcast player found at bottom of this page**)

Q: Please tell us about your current, past, or future career. What do you love most about what you do?

In 2017 I quit my job in government contracting to pursue a career in the wine industry. I started out part-time in the tasting room at Casanel Vineyards and Winery while still at my old job, and I was hooked immediately. My friends there helped me find a fit in this new industry, utilizing my business skills by connecting me with Sean Martin at Boxwood, who happened to be seeking a new manager at the time. I interviewed at three wineries in one day.  Boxwood was my last interview. Before I even walked into the building, I knew this was where I would end up. I love engaging with our customers and creating content that connects them to our brand.

Q: What are a couple of your favorite restaurants in our community?

A COUPLE?! You’re talking to a food and wine lover. To keep things short, I’ll say that here in Middleburg, King Street Oyster Bar and Red Bar Sushi are my go-tos. But, if I really want to treat myself, there’s nothing like having an Old Fashioned at The Red Fox Inn & Tavern’s cozy upstairs bar before one of their amazing filet mignons paired with a bottle of Boxwood Reserve.

Q: How long have you lived or worked in our community?

I moved to Virginia in November of 2009. I had only planned to be here for a year or so and … well … here we are! I think it’s safe to say I enjoy NoVa.

Q: If you could travel anywhere in the world right now, where would it be and why?

Bora Bora to stay in an overwater bungalow – isolation never sounded so good.

Q: What is one of your favorite movies? TV shows?

Harry Potter series / Criminal Minds.

Q: What advice would you give to people?

Get to know yourself better.

Q: What is something on your bucket list?

A month in Tuscany, living like a local.

Q: What is your go to band when you can’t decide what to listen to?

Taylor Swift – she is an absolutely brilliant songwriter.

Q: What is your favorite thing or something unique about our community?

I like that Middleburg is this odd little bubble of escape. People from so many different areas travel here to enjoy the countryside and just breathe. I get to meet so many of them working at Boxwood, and I hope that I contribute to their relaxations and rejuvenation before heading back to their daily grind.

Q: Where do you see yourself in 5 to 10 years?

Hmmm … I would like to have my WSET 3 certification by then, and continue working with oenophiles as we go down the rabbit hole exploring the world of wine together. I haven’t really found that anything else bonds people together like food and wine, so I know that will still be part of my life in some way.

Q: What is the most beautiful place you have ever been?

Sedona, AZ – hands down! It’s absolutely magical. I think it should be a requirement for everyone to do a bit of soul-searching in the desert.

Q: Favorite month? favorite holiday? and best single day on the calendar?

Even though I haven’t been in school for QUITE a while, September and Back to School season has always been my favorite time of year. For me, it’s a time to reevaluate accomplishments and goals, identify the loose ends I want to wrap up before the end of the year, and of course take advantage of the back-to-school sales on all the fun stationery items I “need” to get there! The weather starts to get cooler, the holidays are on the horizon, and those gorgeous grapes are ready to be picked. It’s just the best.

Q: What would you rate a 10 out of 10?

Boxwood Reserve!

Q: Who inspires you to be better?

My dad.

Q: What are one or two of your favorite scents?

Vetiver … Coconut is a close second.

Q: Finally, what 3 words or phrases come to mind when you think of the word HOME?

Cozy, Calming, Cats 🐾

Dorothy Vaccaro as a featured guest on the Real Estate, Wine, & More Podcast: