When to Road Trip Virginia:
Spring, summer, and fall are all beautiful times to visit Virginia. Even in the mountains, we don’t get a lot of snow, so winters aren’t the most scenic. Peak fall foliage is in October & November, with higher elevations seeing the first color changes.
There is so much to do in this part of Virginia! We love historic sites just as much as we love hiking and off-roading, so we have written two road trips itineraries for Virginia. Check out our History Lovers Virginia Road Trip Itinerary here. For both 4 day Virginia road trip 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
Luray Caverns
Visit the largest caverns in the eastern US. Wander the paved and lit pathways through the canverns. Hear the Great Stalacpipe Organ fill the cavern with music and make the stalactites sing. And don’t miss the mirrored optical illusion of Dream Lake.
Your ticket includes entry to Toy Town Junction, Car and Carriage Caravan Museum, and Shenandoah Heritage Village. 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.
Three hikes you might enjoy on the way are the 2.4 mile out & back Rose River Falls, the 5 mile South River Falls loop, or the 4.6 mile out & back Blue Ridge Tunnel.
Drive to Charlottesville
Leave Skyline Drive and drive 30 minutes to Charlottesville. We recommend enjoying dinner at one of the many restaurants in the Downtown Mall.
Day 2 – Charlottesville
2 hours of driving, not counting the off-roading trail
Hiking on the Blue Ridge Parkway
Start the morning with a hike at Humpback Rocks. Drive a few extra minutes and stop at Ravens Roost Overlook, one of my favorites.
Off-Roading at Big Levels
Start Big Levels 4×4 Trail at Coal Rd and Mt Torrey Rd in Lyndhurst. Take your lunch and plan 4-5 hours to complete the trail north to south. When you’re done, return via the Blue Ridge Parkway, stopping at overlooks along the way.
Blue Ridge Parkway Scenic Drive
Return to the Blue Ridge Parkway and continue south to Natural Bridge.

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.
The state park includes 7 miles of hiking trails. Cedar Creek Trail continues beyond the bridge to Monacan Indian Village and Lace Falls.
Skyline Trail Trailhead
Just a few minutes’ drive from the Natural Bridge parking lot, you’ll find the .6 mile trail to Jefferson Point. Put your receipt from the state park on the dash and cross the street from the parking lot to find the trail. You’ll also notice a kids nature exploration area adjacent to the parking lot.
Some other things you might enjoy: Virginia Safari Park, Caverns at Natural Bridge, Dinosaur Kingdom II, and The Pink Cadillac Diner.
Drive to Roanoke
Take the highway or the Blue Ridge Parkway to Roanoke.

Day 4 – Roanoke
1 hour of driving
Roanoke River Greenway
Walk, run, or bike along the Roanoke River Greenway, which stretches all along the river from one side of town to the other, with multiple trailheads and crossing multiple bridges and parks. Roanoke has a bike share program with 10 locations or you can rent bikes from Downshift or Roanoke Mountain Adventures. Find a detailed map of the greenway here: https://www.playroanoke.com/roanoke-river-greenway/
Hiking on the Blue Ridge Parkway
We originally set out to do the .7 mile Roanoke River Trail, but that portion of the Blue Ridge Parkway was under construction. Instead, we ended up at the Mayflower Creek parking area (GPS coordinates: 37.243795, -79.856468). The trail to the right led down towards the Roanoke River and connected with the Deer Run Trail, which we followed to the River Walk Trail and down to the water.
Mill Mountain
End the day with a drive 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.
Some other things you might enjoy in Roanoke: Mill Mountain Zoo, Scratch Biscuit Company, Treetop Quest, Blue Cow Ice Cream, the free Star Line Trolley, Virginia Museum of Transportation
Extend the Trip
Here are a few options for extending your trip into a 5 day Virginia road trip itinerary or even longer:
Start in Front Royal at the north end of Shenandoah National Park.
Add a day in Charlottesville for historic sightseeing, winery visiting, or apple picking.
End the road trip in Richmond and enjoy Belle Isle Park, the Maymont Gardens, or Agecroft Hall.
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
