When to Road Trip Virginia:
Virginia is packed full of history and you can enjoy it in any season, but if you want beautiful trees in the background of your historic home photos, you’ll probably want to visit between March and October.
The mountains of Virginia have a lot to offer! We love historic sites just as much as we love hiking and off-roading, so we have written two road trips for Virginia. Check out our Hiking & Offroading Virginia Road Trip here. For both 4 day Virginia itineraries, we’ll start our road trip in Luray, visiting Shenandoah National Park, Charlottesville, Natural Bridge, and Roanoke.
Day 1 – Luray
3.5 hours of driving
Not only is Luray Cavern the home of the largest caverns in the eastern US, but your ticket also includes entry to Shenandoah Heritage Village. Wander the historic 19th century farm buildings before stopping in at Toy Town Junction or the Car and Carriage Caravan Museum.
Some additional things here you might enjoy: Garden Maze, Rope Adventure Park, and the wooden Virginia LOVE sign.
Skyline Drive and Shenandoah National Park
Enter Shenandoah National Park at Thornton Gap and enjoy a scenic 2.5 hour drive to Rockfish Gap in Waynesboro.
Drive to Charlottesville
Leave the national park and drive 30 minutes to Charlottesville. Walk the Downtown Mall and have dinner at one of the many restaurants on this brick pedestrian street.
Stay overnight at one of the beautiful historic inns like Oakhurst Inn or Dinsmore Inn at the University.
Day 2 – Charlottesville
2 hours of driving
University of Virginia Campus
Grab coffee and spend an hour walking through this historic campus. You won’t want to miss the Rotunda, Edgar Allen Poe Room, University Chapel, or the Memorial to Enslaved Laborers.
Drive just a few minutes out of town to Thomas Jefferson’s home Monticello and James Monroe’s Highland. Spend the afternoon learning about these two presidents, their historic properties, and the enslaved people who worked there.
Some additional things you might enjoy in this area: Carter Mountain Orchard or one of the area’s many wineries.
Drive to Natural Bridge
Continue south to Natural Bridge, taking the Blue Ridge Parkway Scenic Drive if time allows. Stay overnight at the Inn at Forest Oaks or the Natural Bridge Historic Hotel.
Day 3 – Natural Bridge
1 hour of driving
Natural Bridge State Park
One of the most incredible rock formations in the entire state, the 215-foot-tall bridge shaped limestone gorge is a must-see. After descending 167 stairs from the Visitor Center, the bridge is just a short walk away. This is a popular spot in the summer months, so we recommend going early. And don’t miss the beautiful nature mural LOVE sign near the steps.
Lunch at The Pink Cadillac Diner
Indulge in some 50s nostalgia and maybe a milkshake while you have lunch at the Pink Cadillac Diner.
Some other things you might enjoy in this area: Virginia Safari Park, Caverns at Natural Bridge, and Dinosaur Kingdom II.
Drive to Roanoke
Take the highway or the Blue Ridge Parkway to Roanoke. If you arrive early enough, head up Mill Mountain to see the Roanoke Star. This iconic spot is also a beautiful overlook of the city. Take a walk around the wildflower garden and pop into the discovery center to view their interactive exhibits.
Stay overnight at Hotel Roanoke or The Liberty Trust, a historic bank transformed into a stunning hotel.
Day 4 – Roanoke
1 hour of driving
Historic Spots in Town
Grab some breakfast at Scratch Biscuit Company and do a little antiquing at Black Dog Salvage. Don’t miss the beautiful Stone House next door. Nearby the Mountain View Recreation Center is now housed in a beautiful historic home.
You’ll want to be sure to visit the Hotel Roanoke (or perhaps have stayed there overnight). Nearby you’ll also find Taubman Museum of Art or if you enjoy beautiful old churches, St. Andrew’s Catholic Church.
Some other things you might enjoy in Roanoke: Mill Mountain Zoo, Treetop Quest, Blue Cow Ice Cream, the free Star Line Trolley, Virginia Museum of Transportation, or a longer drive on the Blue Ridge Parkway.
Extend the Trip
History lovers will find plenty of options to extend their Virginia road trip to 5 days or even longer:
Spend an additional day in Charlottesville, so you can take your time at each site.
Add a stop in Lynchburg to see Poplar Forest, the private retreat of Thomas Jefferson and UNESCO World Heritage Site.
Add a stop in Richmond to see Belle Isle Park, the Maymont Gardens, or Agecroft Hall.
End the road trip in Williamsburg, Yorktown, and Jamestown to see historic colonial and early settlement sites.
Find more Virginia Itineraries:
4 Day History Lovers Virginia Road Trip
4 Day Hiking & Off-Roading Virginia Itinerary
Charlottesville 3 Day Itinerary
Lynchburg 3 Day Itinerary
Roanoke with Kids
Big Levels Off-Roading
3 Virginia Campgrounds