Even though it was our first time in central Virginia, something felt familiar about the wooded hills we were driving through.
“Why does this landscape remind me of a painting in an American history book?”
Oh. Right. Because it’s exactly the kind of landscape that would have been a backdrop to the colonial-period events we learn about in school. The same kind of tree-lined ridges probably rolled right through the Jamestown Settlement, the Lost Colony of Roanoke, and other landmarks memorialized in art, legend, and the bold print in history texts.
Our destination was Charlottesville, a charming small town near the Blue Ridge mountains in the heart of Virginia’s wine country and just a couple hours south of Washington DC.
Here are some sights to check out while you’re there, as well as places to refuel.
1. Outside of Town: Presidents and Pinot
Three U.S. presidents made their homes in the region, and all three properties are open to the public with daily house tours.
- Monticello – the impressive, innovative, and, in some ways, quirky house Thomas Jefferson designed for himself. We were able to visit and will be telling you more about it in a separate post.
- Ash Lawn-Highland – James Monroe’s home, also in Charlottesville near Monticello.
- Montpelier – James Madison’s home, which is about 25 minutes away in the town of Orange.
Eat + Drink
While there is a cafe at Monticello, we opted instead for lunch at the nearby Michie Tavern, a historic site itself with a museum, shops, servers in 18th century garb, and a killer buffet. (Seriously. You’ll be hearing more about that, as well.)
Intertwined with these sites is wine country. Thomas Jefferson was instrumental in bringing wine grape cultivation to the U.S., so the historic roots of the area’s vineyards run deep. You’ll probably pass several en route to visit the presidential residences.
- My cousin’s wedding was at Trump Winery – yes, it’s owned by that Trump family. But considered on its own, it’s a gorgeous venue with good food and good wine. If you feel the product trumps politics, you can stop in for an afternoon tasting.
- We enjoyed a bottle of wine from Prince Michel Vineyard & Winery, which is located in Leon, north of James Madison’s Montpelier. They have a barrel cave with a wine shop above it and offer events like Sunday brunch and paint nights.
- The Jefferson Vineyards are located on the grounds where Thomas Jefferson had wanted to establish a commercial vineyard.
2. Pedestrian Perfect Downtown
The historic downtown street has been replaced by a brick walkway with trees, benches, restaurant seating, and sometimes vendor booths and buskers. On either side are lots of places to shop, eat and drink, an ice skating rink, a movie theater, and an outdoor concert venue.
The wide walkways allow plenty of room for community events, like First Night Virginia, a performing-arts-centered celebration on New Year’s Eve.
You can see a short film on Vimeo about the history of downtown Charlottesville and the pedestrian mall.
Eat + Drink
We spent most of our time in the downtown area.
- The Omni Charlottesville Hotel, where we stayed, basically opens right up to the downtown mall. It has a restaurant and a sporadically-open coffee shop in the lobby.
- Mudhouse, on the other hand, seemed like it was open (and busy) every time we passed by (actual hours are 7a-10p most days). They have really good coffee. In fact, they were on USA Today’s Top 10 coffee shop list and a Roast Magazine micro roaster finalist.
- Timberlakes – drug store/soda fountain/sandwich shop opened in 1890. I tried the staff’s highly-recommended pimento cheese sandwich, which turned out to be basically a cold cheese log and spread on toast. All that to say, I’d recommend going there for the drinks. The front of the store also has any drug store essentials you might need.
- South Street Brewery – while they do have seriously good burgers, their offerings go beyond typical pub fare to include a really nice variety of salads and delicious desserts. The beer drinkers at the table seemed happy with that too.
3. University of Virginia
The UVA is just over a mile from downtown, so a little of that college town vibe still seeps over.
There’s a free trolley that runs between the Downtown Mall and UVA with stops at the Amtrak and Greyhound Bus Stations.
Thomas Jefferson himself founded the university and (probably) designed its famed rotunda, a UNESCO world heritage site – along with the rest of the Academical Village and Monticello. The rotunda is currently undergoing renovations and is due to reopen this summer.
Eat + Drink
Next to the campus is a series of craftsman-style former student resident buildings that have been converted into the Oakhurst Inn and cafe, where we got breakfast on the way out of town. We called about 10 minutes ahead, and they had my insanely good breakfast sandwich and coffee ready for us to pick up when we got there.
Monticello Artisan Trail
The Monticello Artisan Trail winds through this entire area. Formerly known as the Monticello Wine Trail, it includes wineries, breweries, farms, artisan studios, and galleries.
I’d love to go back and spend more time in the area.
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Revolutionary War painting by Henry Alexander Ogden (c. 1897). Public domain.
Thank you to Visit Charlottesville for assisting us with this trip. We were guests of Monticello and Michie Tavern when visiting each site. We received media rates for our stay at the Omni Hotel Charlottesville and a complimentary bottle of Prince Michel wine.
My aunt, uncle, and cousin 
