Charlottesville, Virginia is primarily known as a presidential incubator, but there is much beyond the city’s famous sons, Thomas Jefferson and James Monroe. Consistently ranked as one of the best cities to live, Charlottesville offers a variety of vacation-worthy experiences. The best news? It’s right up the road from Raleigh so you won’t have to worry about checking a bag or sharing your airline seat with the friendly sleeper next to you. While fall is prime time in Virginia for foliage and weather, the city is enjoyable all year round.
Wine & Beer Trails: From Pippin Hill to Early Mountain, the areas just west and just east of Charlottesville are fantastic for wine and beer lovers alike. Want to pack a picnic and take a scenic drive? Start at Afton Mountain Vineyards and eat on their patio while enjoying stunning views of the Afton Mountains, head on over to the brand new Septenary Winery and enjoy the cozy farm setting while you taste their superb Summer Kitchen Rosé, make a pit stop at King Family Vineyard in Crozet to enjoy a walk among the polo ponies, and make it back to downtown Charlottesville in time for dinner at The Local in Belmont. If wine doesn’t suit your particular tastes, follow the Brewridge Trail to visit local craft breweries and cideries in the area. The Brewridge Trail often crosses right over the wine trail, so groups with varying interests can still spend much of the day together nestled in the mountains! If you feel like a splurge, check out Blue Ridge Wine Excursions to set up a private winery or brewery tour.
Jefferson’s Monticello: Not only is the mansion at Monticello an architectural feat, but the property is chock full of history pertinent to the Charlottesville area. Visit Jefferson’s Monticello and take a tour to better understand how this area bore not one, but two presidents. Take in the surroundings from the garden and learn an important lesson in how Jefferson kept his slaves and what life was like at Monticello from their perspective. There are several tour options at Monticello, including a Behind the Scenes Tour and The Hemings Family tour. Slavery is a part of the Charlottesville story, and Monticello provides a sensitive and factual look on the matter. “The Hemings family remains one of the best documented enslaved families in the United States. Decades of documentary research, archaeological analysis and oral histories of Hemings descendants provide related narratives of struggle, survival, and family bonds across generations. 
Their story echoes the history of race and slavery in America.” You can learn about the complete history of the Hemings Family through the 1 hour and 45-minute interactive small-group tour. For General and other tour options, visit the Monticello Ticket page.
The Downtown Mall: The Downtown Mall in Charlottesville is perhaps one of the most charming pedestrian malls in the country. Old-fashioned street lamps illuminate the walk while UVA flags hung on every corner cheer on the basketball and football teams, depending on the season. The mall is home to a charming array of local boutiques, restaurants, and used book stores, ending at the Pavillion, an outdoor concert venue where locals and famous musicians alike take to the stage to entertain their audiences. While you’re down there be sure to check out Spring Street Boutique, Gearhearts Chocolates, and the local theatre, Live Arts.
Bang – 213 2nd Street. Situated just off the downtown pedestrian mall and across the street from a convenient parking lot, Bang offers tapas and artisan cocktails that can’t be beat. Since the restaurant is in an old house, the atmosphere is cozy whether you’re sitting in the refurbished living room, or out in their back yard patio. Martinis on the front porch is a local favorite.
Junction – 421 Monticello Road. Junction offers south western cuisine with a kick. One thing you’ll notice quickly in Charlottesville is a love for reusing old structures. Right in the middle of the Belmont neighborhood, Junction is home to a relaxed vibe and fabulous cuisine in the heart of one of the oldest parts of town. The owners of Junction also own the Local- which is just across the street!
Zocalo – 201 E. Main Street. Zocalo is smack dab in the middle of the hustle and bustle of the downtown pedestrian mall. Lowlit for a romantic and friendly atmosphere, Zocalo serves up Latin American cuisine.
Best Restaurants: BrunchFarm Bell Kitchen – 1209 West Main Street. As a community that loves its wide open spaces, old farms, and rolling landscapes, it’s no wonder there’s an abundance of farm to table restaurants in the area. For one of the best farm fresh breakfasts you’ll ever have, head over to the Farm Bell Kitchen.
The Shebeen – 247 Ridge McIntire Road. In full disclosure, Charlottesville is home to one of our travel advisors, and this is her favorite restaurant for brunch in the entire city. Shebeen puts a South African spin on classic dishes like shrimp and grits, and the results are amazing. If you can only stop into one restaurant for brunch, let it be this one.
Brazos Tacos – 925 2nd Street South. Brazos opened a few years ago as a pop-up experiment in the IX Art Park just off the downtown pedestrian mall, and the owners liked it so much they stayed. Serving up street tacos all day long, the Brazos Breakfast Taco is perfection.
Check out Charlottesville on your own, or call Maupin Travel to set up a driving trip today! There are plenty of overnight accommodations, ranging from vineyard-front B&B’s to 5-star hotels right on the downtown mall. The three and a half hour drive up route one is scenic and easy to navigate, making Charlottesville a perfect weekend or three-day destination from the Triangle. Where will you go right in your own back yard?
