Charlottesville, VA is a quaint college town (actually a city) surrounded by rural Virginia. Considered the Gateway to the Shenandoah National Park, Charlottesville has a beautiful mountain backdrop and much of the city is centered around the flagship University of Virginia. Having historic roots in early colonial days, the area boasts home to the estates of Founding Fathers (and early American Presidents) James Monroe, Thomas Jefferson, and James Madison. 2.5 hours south of Washington D.C, Charlottesville is a fun country getaway and as the slogan Virginia is for Lovers gives way, the people are warm and welcoming.
Timing: Charlottesville is best visited in the Fall and Spring for the weather. Both in the spring and the fall are Foxfield Races, or steeple races which has become a University of Virginia tradition. You can coordinate with the time of the race if you wish to attend, if you do not wish to attend, I would recommend avoiding this weekend since everything will be far more crowded.
Arrive into Virginia and get settled into your accommodation. Charlottesville is easily accessible by train, but for many of the sites you do need a car to get around. I had a couple of friends who were either going to school at UVA or working at the hospital and were great hosts when I visited! Get some dinner and explore the Downtown Mall. Centered around Main street, the Downtown Mall is an 8 block pedestrian mall with a number of restaurants, bars and shops.
Before leaving grab some grub and coffee to go from Paradox Pastry (313 2nd St SE #103). Then start your morning off by visiting Thomas Jefferson’s plantation, Monticello (931 Thomas Jefferson Parkway, Charlottesville, VA). Ironically, the same man who wrote the Declaration of Independence (“All men are created equal”) was also a slave owner. The museum is not skittish of Jefferson’s controversial past. Historic Michie Tavern (683 Thomas Jefferson Pkwy) is a five minute drive from Monticello, for those who may be interested in a glass of wine. Fun fact: the current Nickel depicts Monticello on the back of it.
Both James Monroe’s Highland (2050 James Monroe Pkwy) and James Madison’s Montpelier house museums are local, too. If you have a preference as to which early president’s home you are most interested in! Maybe I should give my home a name and I will become a president!
After getting your fix of history, get your wine tasting on. My favorite vineyard is Pippin Hill Farm and Vineyard (1616, 5022 Plank Rd, North Garden, VA 22959). It is great to sit outside and enjoy wine tasting with a few snacks. If you want to continue, I would recommend Blenheim Vineyards (31 Blenheim Farm, Charlottesville, VA 22902). For those who wish to pack a sandwich for picnic at the vineyards, Ivy Provisions (2206 Ivy Rd) is an upscale deli offering many options.
Come back to town and refresh before going out to dinner at the Ivy Inn Restaurant (2244 Old Ivy Rd), The restaurant serves elevated American food in a charming 19th century home, and I recommend sitting on the patio. The Belmont Neighborhood of Charlottesville also offers many culinary delights. Local (824 Hinton Ave) is another favorite restaurant where you can get great mac and cheese and malbec! You can get a slop bucket from Belmont BBQ (816 Hinton Ave) or Mas (904 Monticello Rd) for some great tapas.
For those who want to get outdoors, grab a coffee from Mudhouse Coffee or Shenandoah Joe Ivy before heading to Humpback Rocks Hike (Milepost 5.8 Blue Ridge Parkway, Lyndhurst, VA 22952). This hike on the Blue Ridge Mountains offers splendid views and can be really magnificent in the Fall.
After returning to Charlottesville, get some well-deserved New York style bagels at Bodo Bagels (505 Preston Ave). Reserve a guided historical tour of the University of Virginia (sign up here). The University was founded in 1819 by Thomas Jefferson, and the original Board of Visitors included Jefferson, James Monroe (who was the sitting President at the time) and James Madison. Do not miss the iconic and Jefferson designed Rotunda. Head back to your accommodation and off back home.
Cheers to a relaxing weekend getaway in Charlottesville, VA!