Charlottesville has deep roots in the wine industry. It started as one of Thomas Jefferson's many visions, and has since earned its place as the “Wine Capitol of Virginia.” Today‚ the federally designated Monticello Viticultural Area has the highest concentration of wineries in Virginia: about 20 of them within a 25-mile radius of Charlottesville. The city's oldest winery‚ Oakencroft Vineyard & Winery, helped lay the path that's grown into the expansive Monticello Wine Trail. The trail includes 23 wineries and five different trails for wine lovers to follow. On the trail travelers will find Jefferson Vineyards, known for its award-winning pinot noir and great views of Jefferson's Monticello property.