Wessex Hundred, a Fitting Chapter in the Storied Career of Simon Smith

Simon Smith’s career has taken him from one storybook setting to the next.

The Vice President of Food and Beverage at The Williamsburg Winery grew up in lush Kent, England, known for its rolling hills, lush garden and iconic castles. Simon accompanied his father, a designer of homes and hotel interiors, often on travels to Spain, Portugal, Amsterdam and France.

“We dined well and that sparked a passion for me in the hospitality business at a young age,” he says. “I actually designed on paper my own hotel. I was about 10, and what I can remember from the elaborate kitchen.”

He took his first job, dishwasher in an English pub, seriously. “It was the old school way of being a dishwasher, no machines,” he says. 

He earned a quick promotion to “salad guy” and then prep cook, enabling him to secure a job as breakfast cook at a nearby hotel. Realizing he needed an education to advance, Simon completed a hospitality management degree at West Kent University.

Fresh out of college, he was hired by Gravetye Manor, a Michelin Star restaurant and hotel nestled in the forest of West Sussex. In his four years there, he finished a management training program, learning every aspect of the business. His final position, sommelier point steward , allowed him to mingle with an affluent crowd — celebrities including Paul McCartney and Eddie Murphy who would drop 1,000 pounds a night on dinner and lodging.

“That was really icing on the cake,” he says. “That took me into the wine world.”

By the time he was 21, Simon was the first Brit to be hired in the cellars of renowned winemaker Louis Jadot in Burgundy, France. He lived in a hostel, teaching himself French with cassette tapes while he drove.

“What an incredible experience. I put everything into it you can imagine,” he says. “I learned how to be a Burgundian French person.”

Napa Valley called him after that. It was 1997 and his words to his mum upon leaving England, “I’ll be back in 18 months.”

Simon hasn’t left the United States since. Other stops prior to The Williamsburg Winery included the Boar’s Head Resort in Charlottesville and Blackberry Farm, luxury accommodations in the Smoky Mountains. Three years at Wyndham Hotels & Resorts followed by three years at Bluegreen Vacation Ownership introduced him to the corporate world.

The Williamsburg Winery crystallizes each of those experiences. “It reminds me of Burgundy, it reminds me of Gravetye and of Blackberry — all the places I’ve been and literally everything I’ve done,” he says. “Here it is nestled in Williamsburg, where there’s so much opportunity. It was fitting for me and the Duffeler family was exactly the type of family I wanted to work for. It was a good fit.”

Simon oversees Wedmore Place, The Williamsburg Winery hotel, events and the Gabriel Archer Tavern. The avid cyclist also runs The Williamsburg Winery Cycling Club, which member exceeds 500. He logs as many as 4,000 miles annually, time to lose himself in an outdoor, electronics-free world, a mindset he and his wife, Lori, instill in their four children.

“It’s so diverse and I love that about this industry,” he says. “You can have a plan for the day, and it may get thrown up in the air by the end of the day. It’s so much fun. Since I was 14 years old and going back to that dishwasher job, it’s the excitement of people, of working with them and trying to make things better every day, that I enjoy. I’ve got a great team. It’s the people who make it. The farm is beautiful, but the people make it.”