Nestled to the northeast of Charlottesville, Orange County is best known for two things: President James Madison and grapes. In the town of Orange, the James Madison Museum has exhibits dedicated to the nation's fourth president. Madison's estate, Montpelier, is just to the southwest and has undergone a restoration project. The 3,000-acre/1,215-hectare estate has about 100 buildings, as well as its own steeplechase course and an array of walking trails through the James Madison Landmark Forest. The African-American Cemetery holds the remains of many of the laborers who worked on the estate.

Not far away from Orange are Barboursville and Gordonsville, where you can visit some of the state's most noted wineries. Barboursville Vineyards was once the estate of Virginia Governor James Barbour. His good friend Thomas Jefferson designed the estate's original mansion, which burned down in the 1880s. In summers you can catch the performance series "Shakespeare at the Ruins." Horton Cellars in Gordonsville makes a number of wines as well, including some noted Rhone-style wines.

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