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. Though the well-known Oakencroft Vineyards recently closed due to the retirement of its owner, there are several other wineries near Charlottesville, including Jefferson Vineyards (established in 1986), Barboursville Vineyards, Horton Vineyards, Sugarleaf Vineyards, and First Colony Winery, among many others.
Another great idea is to visit Carter Mountain Orchard, where you can pick your own seasonal fruit (Peaches, cherries, apples, etc) depending on the time of year. Check out their calendar to see what special events they have going on. They open up at 9 am and it is a great way to spend the morning.
If your stay includes a Saturday morning, you must pay a visit to the Charlottesville City Market - by far one of the best 'farmers markets' around. While it get's a bit crowded, there is an inspiring display of local goods including, fresh produce (of course), local artisans (jewelry, paintings, pottery, hand-sewn items), fresh brewed locally roasted coffee, baked goods - you can even get breakfast with fresh crepes made on-the-spot, hot empanadas, hot bagels, etc. Usually there is some sort of live music.
After your visit to the local market, you can stroll over to the historic downtown mall area - a pedestrian mall surrounded by unique shops, rare & used book stores, restaurants & cafes, and much more. Enjoy some time milling around, have lunch outside - and take in the general ambience of the historic downtown area.
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While strolling down Main Street , take note of two bronze sculptures: George Rogers Clark Memorial and Lewis and Clark. Clark is a native son of Charlottesville and led the spectacular winter attack on the British at Fort Vincennes. He is largely responsible for the exploration and opening of the Indiana Territory . Capt. Meriwether Lewis received his commission to head the Corp of Discovery from President Jefferson in the summer of 1803 and departed from Charlottesville to head for Pittsburg to obtain the boats to be used by the Lewis and Clark exploration trip of the Missouri River .