Thomas Jefferson lived in Albemarle County and is thought to be one of the first Americans to experiment with winemaking, however, the industry here wouldn't begin to flourish until the 1990s. Today, there are more than 40 wineries within a 25-mile radius of Charlottesville as part of the Monticello Wine Trail. Wines from the Monticello American Viticultural Area are considered some of the best in the Eastern United States. Plan your perfect vineyard hopping experience by exploring the wineries on the passport below.