The Best Road Trips in Virginia

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There are two common threads woven into the fabric of the best road trips in Virginia. 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 car insurance comparison shopping and brokerage app, Jerry, offers comprehensive roadside assistance at an irresistible price.
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

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.

What you should do

Start at the westernmost tip of Virginia, where you’ll explore the Cumberland Gap. This mesmerizing national forest straddles three states—Virginia, Kentucky, and Tennessee.
Be sure to visit Gap Cave and Pinnacle Overlook, and hike to Skylight Cave.
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.
Next, you’ll want to take High Knob Road to the High Knob Lookout Tower and recreation area.
To see some lovely waterfalls, you’ll want to head east to the Little Stony Falls.
This western tour of Virginia is just three hours of driving.
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
Of course, America’s most famous hiking route, the Appalachian Trail, passes through Virginia as well.
Railroad tracks running through Natural Tunnel State Park, Virginia
Natural Tunnel State Park

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

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!

What you should do

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.
Start this historical adventure at the Manassas National Battlefield Park, where the infamous Battle of Bull Run took place. 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.
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.
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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An old Civil War era house still stands in Manassas National Battlefield Park
Manassas National Battlefield Park

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

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

Entrance into the 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.
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 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.
A clear sky on a cold day on a scenic stop along Shenandoah National Park’s Skyline Drive
Shenandoah National Park’s Skyline Drive

Virginia Beach and the Chesapeake Bay Bridge-Tunnel

We all know about the famous Highway 1 bridge connecting mainland Florida 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, Maryland or Myrtle Beach, South Carolina.

Why you should go

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

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?
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.
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. Your kids will adore the Atlantic Fun Park and Ocean Breeze Waterpark, too.
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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Sunrise sighting on the shores of Virginia Beach
Sunrise at Virginia Beach

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 California and 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

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

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.
A cloudy day at a winery in the village of Bluemont,Virginia
Virginia wine country

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 Jerry, 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, too. Jerry can show you up to 50 quotes from reputable insurance companies and help you quickly and easily compare their policies.
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!
Jerry blew my mind, honestly. From start to finish, using the app took me 10 minutes and I ended up with $100 of savings a month. Best of all, customer service answered all my questions about rental car reimbursement and roadside assistance.” ––Savanna R.
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