Really any drive through Virginia is a historical one, but these eight routes are especially loaded with attractions and scenic opportunities. No matter the direction you're headed, you can find a great amount of Virginia history along the way.
Journey Through Hallowed Ground
A trek down US Route 15 will put you on the Journey Through Hallowed Ground, one of the most historically significant drives in America. The National Heritage Area actually includes land from Monticello all the way to Gettysburg, PA. Your Virginia itinerary could include stops to admire Shenandoah National Park or learn something new at the Exchange Hotel Civil War Museum.
Road to Revolution Heritage Trail
The Road to Revolution Heritage Trail can take you on a historical trip through Central, Northern, and Coastal Virginia. Trail highlights include the presidential home heavy-hitters—Monticello, Mount Vernon, Montpelier, and more—as well as key sites like St. John's Church in Richmond and the James Monroe Memorial Museum and Library in Fredericksburg. Get the map to start exploring.
US Civil Rights Trail

Head south from Richmond to explore the US Civil Rights Trail. Centered around the Robert Russa Moton Museum in Farmville, the trail covers 300 miles and 41 sites that touch on the civil rights in education struggles of Black Americans, Native Americans, and women from the 18th to 20th centuries.
Jamestown Discovery Trail
East from Richmond is the Jamestown Discovery Trail, which follows US Route 5. Sites along the way include presidential homes, plantations, and Native American sites. The trail ends at Jamestown Settlement and Historic Jamestowne.
If you find yourself in Southwest Virginia, you could easily traverse multiple trails at once.
Coal Heritage Trail
Along the 300 miles included on the Coal Heritage Trail, you can explore a range of attractions that demonstrate the influence of coal on the region. See mining equipment, railroad buildings, and more historic items at places like the Harry W. Meador Coal Museum in Big Stone Gap and the Pocahontas Exhibition Mine and Museum in Pocahontas. Use this trail map to start planning.
Crooked Road Heritage Music Trail

Find your next top artist on the Crooked Road Heritage Music Trail, which spans more than 300 miles and connects 60 venues of varying sizes. Learn about the musical history of the region all while tapping your toes to some quality Appalachian old time and bluegrass music. Start exploring the mountains of music.
Daniel Boone Wilderness Trail
The Wilderness Road traces the primary route taken by western settlers as they moved down the Shenandoah Valley and into the Southwest Virginia area. A total of 23 localities on this trail down US Route 11 and into the Blue Ridge Highlands gives you plenty of options for a weekend trip.
Virginia Civil War Trails
Civil War Trails span all across Virginia, branching off this way and that. Look out for interpretive signs that could lead you down back roads to battlefields, museums, and more historic sites.