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Travel Guide: Charlottesville, VA

We visited Charlottesville, VA over the winter, and enjoyed our time learning about Thomas Jefferson's Legacy, doing all the wine tastings, and exploring downtown!


When visiting Monticello, there's a ton to learn (and un-learn) about Thomas Jefferson and his legacy as President and architect, and his complicated history with slavery. The Virginia Wine Trail is as good as it gets down there, dozens of wineries with lavish scenery, live music, and of course great booze. And don't miss Charlottesville's charming downtown which has one of the longest pedestrian malls in the U.S. It's filled with restaurants, antique stores, bookshops and more, culminating in an outdoor concert venue at the end. We walked around the mall during lunch, however I'll warn you to maybe plan around what day/time you visit, for some shops/restaurants may be closed on certain weekdays, and only open for a few hours each day. The Dairy Market is new and buzzing though, with plenty of seating and good eats to enjoy.

 

Thomas Jefferson's Legacy: Monticello, University of Virginia, and other unsavory bits of history


If you know anything about Charlottesville, its probably that its home to UVA and Thomas Jefferson's Monticello. Thomas Jefferson, the 3rd President of the United States, called Charlottesville his home and built his house over a forty-year period on top of the mountain he'd later call Monticello. We booked tickets ahead of time to visit Monticello on our first full day, and it truly is a beautiful estate, albeit complicated.

Photos from when I visited Monticello in the summer

Here's a little history lesson if you're not familiar. Jefferson is known for what he dubs his three greatest achievements: the primary draftsman of the Declaration of Independence, the primary draftsman of the Virginia Statute for Religious Freedom, and the Father of the University of Virginia. While Jefferson is one of the most important founding fathers, it is still a painful and complicated story, for he's also known for is enslaving over 600 people, freeing only ten of them in his lifetime.


The guides at Monticello are committed to educating you about Thomas Jefferson, the ideas of freedom, and the realities of slavery that made the United States. The exhibits about Sally Hemmings are particularly enlightening, and I encourage you to carve out a few hours of your trip to learn more!

Thomas Jefferson also founded the University of Virginia, which we walked around one morning, checking out the campus. The Lawn is a must see. When UVA was founded in 1819, the campus was centered around a library. By today’s standards, this seems to be common practice, but back then, universities were traditionally structured around a church, and this was considered radical.

 

Wineries, Breweries, and Cideries, oh my!


Besides (and better than) Thomas Jefferson, Charlottesville is known for the wineries! On the second full day, we headed west of the city for a responsible day of drinking. Our first stop was King Family Vineyards. Getting there early had its perks - we had the entire place to ourselves, save for Frank the cat. It was beautiful there with majestic swans and overlooked a large polo field. We then stopped for a tasting at Veritas Winery, which had the best wines of the trip. We tasted their sauvignon blanc, viognier, and claret, all of which we ended up buying a bottle of.


After wine tasting, we headed further south to check out a brewery and cidery in the area. We had a late lunch and good beer at Devil's Backbone, and then ended our afternoon with a cider flight, which I loved, at Bold Rock Nellysford Cidery.

In vino veritas - In wine, there's truth.

I also visited Charlottesville on a girls' trip the year before, where we spent a day wine tasting in Barboursville just north of the city. While on that trip, we visited Keswick Vineyards, Castle Hill Cider, and Barboursville Vineyards. These are great options if you are driving from DC, since they're on the northern side. Keswick was intimate with live music the day we were there, Castle Hill was a fancy white mansion with an upscale patio, while Barboursville was easily the most popular venue, with some historic Thomas Jefferson ruins on site.

 

Charlottesville Eats

We grabbed coffee and pastries at Marie Bette and Farm Belle Kitchen in the mornings to fuel up for our busy days. We had a quick lunch between UVA & Monticello at Revolutionary Soup along Charlottesville's pedestrian mall. We also grabbed lunch at Devil's Backbone while we were out winery and brewery exploring. If you have an afternoon to spare, head to Three Notch'd Brewing Company for happy hour. Lots of great beer (I loved all of their Goses), and located in a cool art park to top it off.


For an easy dinner, we stopped by The Whiskey Jar, which came highly recommended and had great burgers and cocktails. We got lucky that there was a crew of fantastic jazz musicians playing that night as well. We ate a fancier dinner from Orzo Kitchen and Wine Bar, complete with Mediterranean appetizers and wine.


By far, my favorite parts of the foodie scene in Charlottesville were our makeshift winery snacks! We snagged a box of decedent chocolates from Kilwins downtown and bread ends and House Dressing from Take It Away at the Dairy Market. The House Dressing is a unique spread for use on sandwiches or salads, but paired with their daily $0.75 bread ends made for an excellent winery snack.

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