Hospitality | Tourism 2025: WOOLARD, KERRY

Woolard manages operations for the 1,300-acre winery and estate purchased by the Trump family in 2011 after Patricia Kluge declared bankruptcy. Eric Trump Wine Manufacturing now owns the property, which includes a hotel and event facilities, and Eric Trump is its president.

Billed as the state’s largest winery, the business opened a cidery business in 2024, offering five hard ciders and planting 6,000 apple trees that will eventually provide the apples used in the drinks. Along with other Trump family businesses, the property has seen media scrutiny for hiring foreign seasonal workers while President Donald Trump leads an immigration crackdown.

A William & Mary alumna, Woolard joined Trump Winery as its general manager in 2012, after having served as general manager at King Family Vineyards and First Colony Winery.

Woolard, who spoke at the 2016 Republican National Convention, serves on the board of the Free Enterprise Forum.

WHAT MAKES ME HAPPIEST: Having a nice glass of wine at the end of the day, having worked on my farm in Nelson County or in the garden surrounded by our goats and ducks with my partner, Craig, and our rescue dog, Frankie.

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