If you have a little extra time, a car and an urge to catch some of the sites that might elude some of your fellow travelers, Charlottesville and Albemarle County has plenty to offer just a little ways from the historic city proper.

Most visitors to Charlottesville will undoubtedly check out Monticello , Thomas Jefferson’s magnificent self-designed estate, and perhaps will all stop off down the street at Ash Lawn-Highland , the historic home of James Monroe. But many visitors to the region will miss out on the equally spectacular Montpelier , the grand Piedmont tobacco plantation where the man who served as President between them spent his later years. About 40 minutes outside of Charlottesville, the home of James Madison, 4th President and primary author of the Constitution, is a 2,750-acre estate with 130 buildings set in a breathtaking corner of the Virginia Hills.  

If you do decide to venture further afield, you’ll find yourself right in the middle of Virginia’s wine country, home to a number of vineyards producing great grapes and bottles. One of the most popular, Oakencroft Vineyard , is also the oldest in the region and the closest to the heart of town. Also an interesting find, Jefferson Vineyards began in 1986 producing wines on the site of the historic site of the President’s personal winery, just a mile south of Monticello.