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10 Fun Things to Do in Charlottesville and Central Virginia

Central Virginia offers a mosaic of cuisine, culture, arts and outdoors for residents and visitors of all ages to enjoy.

By Rebecca Treon on November 1, 2023

King Family Vineyards, a part of the Monticello Wine Trail in Central Virginia
Monticello Wine Trail

Central Virginia is full of one-of-a-kind experiences – the region is rich in landmarks with historical significance, stunning scenery with limitless opportunities to get out and adventure, a vibrant live music scene, sporting events (especially of the equestrian kind), and a thriving food and beverage scene centered around the area’s agritourism offerings. 

If you’re a newcomer eager to feel like a local or a visitor looking to plan a three-day weekend, here are 10 fun things to do in Charlottesville and Central Virginia.

1. Get Crafty 

Central Virginia has a burgeoning craft beverage scene that’s worth exploring. You can experience wine, beer and spirits through the Monticello Wine Trail, the Brew Ridge Trail, the Fermentation Farm Trail, the Nelson 151 Trail, or the Corks and Caps campaign, which guides visitors through its award-winning breweries and wineries. 

2. Indulge in Retail Therapy

Charlottesville’s Downtown Mall is one of the longest pedestrian malls in the U.S., featuring more than 150 shops, bars and restaurants. Shoppers can stroll the tree-lined streets and explore vintage shops, stop at a sidewalk cafe and people watch, or catch live music at the Jefferson Theater (built in 1912) and the Ting Pavilion. Or, step outside the city to shop at one of our charming towns in the outlying counties. 

Thomas Jefferson’s Monticello in Charlottesville, VA
Thomas Jefferson Foundation at Monticello

3. Immerse Yourself in History

Central Virginia is at the epicenter of American history. You can visit Montpelier, the home of President James Madison, in Orange County. Monticello, a UNESCO World Heritage site and the home of President Thomas Jefferson is just outside of Charlottesville, and adjacent to Highland, the estate of President James Monroe. 

4. Visit a National Park

Shenandoah National Park meets the Blue Ridge Parkway at Skyline Drive, a 105-mile scenic drive that is popular among foliage followers in the fall and provides access to hiking, biking and horseback riding trails, plus campgrounds, visitor centers and resorts. 

5. See the Steeplechase

In Central Virginia, you can have a front-row seat to horse events at Montpelier Hunt Races in Orange County, Foxfield Races in Albemarle County or HITS in Culpeper County. Also, both Liberty Hall Plantation and the University of Virginia’s Polo Center host interscholastic and intercollegiate polo events throughout the year. 

6. Experience Local Art and Culture

Discover the work of local artisans in Nelson County at HeART of Nelson Artisan Collective and at Crozet Artisan Depot in Albemarle County. You also can attend the Palmyra Arts Fest in the historic Village of Palmyra in Fluvanna County. 

The Boardwalk on Lake Anna in Central Virginia
Melody Robbins

7. Explore the Great Outdoors

Apart from Shenandoah National Park, there are plenty of ways to experience some outdoor adventure in Central Virginia. In Orange County, get an adrenaline rush at Skydive Orange or paddle the day away with the Rivanna River Co., which offers trips along the Rivanna River, a scenic waterway that flows through the counties of Albemarle and Fluvanna. Need more water? Enjoy Lake Culpeper and Lake Anna. The latter is part of a state park and offers campsites and cabins that are available by reservation. 

8. Hit a High Note

Central Virginia has so many ways to listen to live music, including numerous festivals, like the Tom Tom Festival in Charlottesville and the Graves Mountain Music Festival in Madison County. Local bands play at the Rivanna Roots Concert Series, located along the Rivanna River, and well-known artists can also be seen year-round at John Paul Jones Arena in Charlottesville. Oh, and did we mention, Charlottesville is the hometown of Dave Matthews? 

9. Have Fun on the Farm

Central Virginia is well-known for its agritourism. You can do goat yoga at Fischer Farm, or hike over 6 miles of trails at The Market at Grelen, a pick-your-own farm. To get into the cowboy spirit, watch professional bull riders at Oakland Heights Farm or enjoy a Cattle Drive Weekend at Andora Farm. 

10. Taste the Town

In Orange County, Gordonsville holds the unique title of the Fried Chicken Capital of the World and hosts the Famous Fried Chicken Festival each year. Still hungry? Check out the Taste of the Mountains Main Street Festival in Madison County or Oktoberfest at Blue Mountain Brewery in Nelson County. There’s also Harvest Festival held at Albemarle Ciderworks. 

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