The Best Road Trips in Virginia

From gorgeous mountain ranges to incredible engineering marvels, these are the best road trips in Virginia!
Written by Matt Terzi
Reviewed by Carrie Adkins
There are two common threads woven into the fabric of the best road trips in
. The first is history, which the "Old Dominion" state is steeped in. And the second is nature, which that classic "Virginia is for lovers" slogan embodies—this is one of the most beautiful states in the country, with stunning views tucked behind every corner.
From the breathtaking splendor of the Cumberland Gap and the Shenandoah Skyline Drive to one of America’s most incredible engineering marvels spanning the Chesapeake Bay, Virginia is a state worthy of putting your odometer through its paces.
Of course, you don’t want to have a flat tire, dead car battery, or pesky check engine light ruining any of your adventures in Virginia. That’s why the
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Ready for a road tour of one of America’s most scenic states? Let’s take a look at some of the best road trips in Virginia!
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Virginia’s hiking and natural beauty circuit

Virginia is an incredibly beautiful state to explore in your car. But to really enjoy the majesty of the Old Dominion, you might want to stretch your legs with hiking adventures, taking in amazing landscapes from one trail to the next.

Why you should go on a hike through Virginia

Virginia is home to excellent hiking trails that are accessible to adventurers at every experience level. And even if you aren’t big on hiking, this route makes for a fantastic scenic drive through some of Virginia’s most awe-inspiring regions.

Where to go to hike in Virginia

Natural Tunnel State Park
  • Cumberland Gap
    : Start at the westernmost tip of Virginia, where you’ll explore the Cumberland Gap. This mesmerizing national forest straddles three states—
    , and
    . Be sure to visit
    Gap Cave
    Pinnacle Overlook
    , and hike to
    Skylight Cave
  • Natural Tunnel State Park
    : From the Cumberland Gap, take The Wilderness Road (highway 58), all the way down to the Natural Tunnel State Park. From there, head north to The Devil’s Bathtub, a gorgeous drive ending in an excellent hike.
  • The Devil's Bathtub
    : Next, you’ll want to take High Knob Road to the High Knob Lookout Tower and recreation area.
  • Hike Little Stony Falls
    : To see some lovely waterfalls, you’ll want to head east to the Little Stony Falls.
  • If you want more of a hiking challenge, or if you just want to extend your road trip, add a few of these areas in Virginia to your drive as well:
  • Clinch River State Park
  • Cleveland Barrens
  • The Boulder Ledge
  • Buffalo Mountain
  • The Dragon’s Tooth Trail
  • Apple Orchard Falls
  • Bluff Mountain
  • The Three Ridges
  • The Buttermilk Trail in Richmond

An American history tour through Virginia

Since America’s earliest settlers founded Jamestown, the state of Virginia has played an integral role in shaping American history at every pass. Virginia’s historical sites attract huge swaths of tourists each year, and a Virginia historical road trip is quite beautiful, too.

Why you should go on an American history tour of Virigina

There are countless historical sites throughout Virginia, including numerous Revolutionary War and Civil War battlefields and estates belonging to the Founding Fathers.
Amateur historians (and Hamilton: An American Musical fans), start your engines!

Where you should go for an American History Tour of Virginia

Manassas National Battlefield Park
  • This ten-hour historical road trip takes you to the biggest American history spots in Virginia. You may want to split it up into a few days to give yourself some time to explore.
  • Manassas National Battlefield Park
    : Start this historical adventure at the Manassas National Battlefield Park, where the infamous Battle of Bull Run took place.
  • Mount Vernon
    : Then drive to Mount Vernon, the colonial estate of George and Martha Washington. Mount Vernon is just on the outskirts of Washington DC, so consider stopping in for a visit to the nation’s capital, too.
  • Next stop: the
    Fredericksburg Battlefield
    , another important Civil War site. From there, head to
    James Madison’s Montpelier Plantation
    , which is just a short drive from
    Thomas Jefferson’s Monticello Estate
  • Appomattox Courthouse National Historical Park
    : You’ll want to head to Appomattox next. The Appomattox Courthouse National Historical Park is the site where the Confederacy surrendered to the Union, ending the American Civil War.
  • American Civil War Museum
    : Next, go to Richmond and visit the American Civil War Museum before driving to the Petersburg National Battlefield.
  • You won’t want to miss Colonial Williamsburg, a world-famous town where reenactors showcase colonial life in a living, breathing museum. You might be able to visit Yorktown on the same day, including the
    American Revolution Museum
  • The final stop on this historic Virginia tour is Norfolk, home to a massive US Navy base. You can take a tour of the naval harbor and see modern-day warships as they prepare to head out overseas. And you can wrap up your trip with some R&R at
    Virginia Beach
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The legendary Shenandoah Skyline Drive

With a reputation as one of the most beautiful roads in North America, the Skyline Drive in Shenandoah National Park easily deserves a spot on your American road trip bucket list.
Whether you drive this 105-mile road in one shot or make camp somewhere along the way, the famed Skyline Drive is arguably the #1 destination in Virginia for serious road trippers.

Why you should go to Shenandoah Skyline Drive

The Shenandoah National Park is one of the prettiest areas in all of Virginia, and the Skyline Drive takes you on a jaw-dropping tour along its most scenic path. Most of this road lines up with the Appalachian Trail, so hardcore hikers could attempt this lengthy path on foot.
With nearly 70 scenic overlooks, a plethora of great hiking trails, and loads of picnic spots, Shenandoah National Park’s Skyline Drive is an easy contender for one of the most beautiful scenic routes in the US.

What you should do on the Skyline Drive

Shenandoah National Park’s Skyline Drive
  • Entrance into
    Shenandoah National Park
    costs $20 per vehicle and expires after seven full days, giving you plenty of time to explore everything Shenandoah has to offer. Make sure to pack everything you need and fill up your gas tank before you head in.
    Elkwallow Wayside
    : The Elkwallow Wayside has a small shop, but otherwise, you’ll not find many reasons to crack open your wallet here.
  • The
    Skyline Drive
    will take you about four hours to drive from one end to the other. The park’s speed limit is 35 MPH in most places, and you don’t want to exceed that, as there are countless wild animals that call Shenandoah National Park their home.
  • Matthew's Arm Campground
    : Matthew’s Arm Campground is a great place to spend a few nights. Just note that you can’t enter the park with campers taller than 12’ 8" due to a low tunnel along the road.

Virginia Beach and the Chesapeake Bay Bridge-Tunnel

We all know about the famous Highway 1 bridge connecting mainland
with Key West, but did you know there’s an even more impressive engineering marvel in Virginia?
The Chesapeake Bay Bridge-Tunnel
is a true spectacle that offers a gorgeous oceanic view from above (and below) the Chesapeake Bay.
On the southern end of this impressive construction feat is one of Virginia’s most popular tourist destinations, Virginia Beach. It’s a fantastic place to enjoy some fun in the sun, and it’s usually less hectic than Ocean City,
or Myrtle Beach,
South Carolina

Why you should go to the Chesapeake Bay Bridge-Tunnel

It’s difficult to put into words just how incredible the Chesapeake Bay Bridge-Tunnel is. You climb up over the Chesapeake Bay with nothing but ocean all around you. That view alone is worth a visit in and of itself.
But then, in two different intervals, the bridge dips down beneath the sea into tunnels that allow ships to pass overhead. Don’t worry though: it’s perfectly safe. The tunnels enter and exit through man-made islands with plenty of safety between you and the Bay.
Virginia Beach itself is an incredible town with a beautiful, clean beach. Fighter jets buzz overhead constantly as they go to and from military bases in the area. And you’re just a short drive from Norfolk, where you can look at and even tour epic warships.

What you should do

Sunrise at Virginia Beach
  • It goes without saying that the Chesapeake Bay Bridge-Tunnel is easily worth a visit on its own. The only real complaint you might have is that there’s nowhere to stop along the bridge to gaze out over the water. But hey, you can always drive it two or three (or nineteen) times, right?
  • Virginia Beach
    : It’s easy to spend a whole week in the Virginia Beach and Norfolk area and still have things left on your itinerary. Cruising around the boardwalk can keep just about anyone occupied for a whole day. Just make sure you bring a bag for all the souvenirs.
  • Museums to hit: Want to get out of the sun for a while? Bring the kids to see the cool airplanes at the
    Military Aviation Museum
    , or explore the
    Virginia Aquarium and Marine Science Center
  • Activities for kids: Your kids will adore the
    Atlantic Fun Park
    Ocean Breeze Waterpark
    , too.
  • Waterman's Surfside Grill
    : If you enjoy seafood, don’t even question this next bit: go to Waterman’s Surfside Grill and drop $40 on their Ultimate Just Seafood dinner. You’re welcome! Waterman’s is a fantastic restaurant with amazing food for meat-eaters and vegetarians alike.
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Fun for foodies: The ultimate Virginia wine tour

Virginia’s wineries and vineyards are impressive enough to rival some of the greats (or grapes) found in
New York
This list wouldn’t be complete without walking you through the ultimate Virginia wine tour.
Most of Virginia’s best wineries are located in the northern reaches of the state, close to the District of Columbia and the northeastern tip of
West Virginia
That being said, there are great wineries throughout the Old Dominion state, so you may want to stop by them while completing some of the best road trips in Virginia listed here.

Why you should go on a Virginia wine tour

Virginia is home to some of America’s finest vineyards, with wine tastings and wine tours scattered all through the state. If you’re a lover of fine wines, you won’t want to miss this Virginia vineyard road trip.

What you should do on a Virginia wine tour

Virginia wine country
  • Let’s start with arguably the eight best wineries in Virginia’s northern wine country. This route takes about five hours to complete if you drive nonstop. You could always add more wineries to the list too—there are several in this region worth exploring!
Here’s a list to visit in order, from first to last:
  • Blue Valley Vineyard and Winery
  • Breaux Vineyards
  • Sunset Hills Vineyard
  • Stone Tower Winery
  • The Winery at Bull Run
  • Paradise Springs Winery
  • Potomac Point Winery and Vineyard
  • Barboursville Vineyards
There are several other wineries you might want to visit that are a bit further out in Virginia, but they certainly belong on any list of the best wineries in Virginia. These wineries include:
  • The Williamsburg Winery
  • James River Cellars Winery
  • Blenheim Vineyards
  • Chateau Morrisette Winery
  • Veritas Vineyards
  • Virginia Mountain Vineyards
Again, this is by no means a definitive list of the only wineries you should visit in Virginia. There are too many great wineries for us to list.
But these wineries represent some of the very best options in Virginia, and they’re close enough to the rest of the top contenders that you might end up stopping along the way.
This part should go without saying, but please don’t drink and drive.

The perfect roadside assistance for road trips in Virginia

While you’re out enjoying the sightseeing, absorbing the history, and sampling the food, keep in mind that your car is getting exposed to a lot of stress. This stress can quickly shift from the car to you in a roadside emergency.
With roadside assistance from
, you don’t have to worry about breakdowns or other issues. Jerry’s roadside assistance will help with tire services, fuel delivery, lockouts, towing, and more, offering peace of mind so you can enjoy a stress-free road trip.

Finding cheap car insurance

You’ll want to browse the Jerry app for
car insurance
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And Jerry’s a licensed broker too, so it’ll take care of your paperwork, eliminate the need for phone calls, and even cancel your old policy on your behalf.
Jerry users save an average of $879 per year on car insurance. Signing up takes less than a minute and can save you lots of money. Money that would be better spent exploring the best road trips in Virginia!
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