The Best Road Trip Routes in Virginia

Sunset over the Blue Ridge Mountains, Virginia
Sunset over the Blue Ridge Mountains, Virginia | © Aaron Garza/Flickr
Aparna Krishnamoorthy

A road trip is a fun, easy and affordable way to get out and see a lot of the things around you. It can be as long or short as you want it – from weekend getaways to full-week trips. Virginia is a beautiful state with many different things to see, here are some of the top road trip ideas to help scratch that travel itch.

Virginia Beach, Chesapeake and The Eastern Shore

Ocean lovers will agree there are few things better than a beach. Start the road trip in Virginia Beach, one of the longest stretches of beach anywhere, with over 35 miles of coastline to enjoy. Once you’ve had your fill of the boardwalks and waterfront, drive east via the Chesapeake Bay Bridge-Tunnel to the Eastern Shore of Virginia. Here you can enjoy the pristine beach with undisturbed wildlife. Continue on north with a stop at the quaint town of Charles City, and then further to Onancock from where you can take a ferry for a day tour of Tangier Island. Tangier Island is a small oyster and fishing island that will take you back in time, along with the sounds of gulls and other bird life. Finally, go further north and stop near the Virginia-Maryland line, at Chincoteague and Assateague islands where you can see wild ponies!

Chesapeake Bay, Eastern Shore, Virginia

Skyline Drive

This is a fantastic way to enjoy the great outdoors. Skyline Drive, which you start at Front Royal (70 miles from DC), is a 105-mile stretch of road that goes through Shenandoah National Park. Make as many stops along the way to last for days, with hiking and camping all along the route. There are over 75 scenic overlooks, multiple hikes of varying levels, and waterfalls, making this one of the nicest mountain drives in the area. Fall is a great time to see the lovely foliage and colors, but summer and spring are equally wonderful with lush greenery and wildlife. Visit the National Park Service website to learn more about camping permits needed.

Skyline Drive


There are over 200 wineries across the state so for a winery road trip, it’s best to pick a region, have a designated driver, and start tasting your way through. The Loudoun Wine Trail is an easy getaway from Washington, DC and is home to a number of scenic wineries, little towns with fantastic dining, and plenty of bed and breakfasts for comfortable overnight stays. The Monticello Wine Trail in Central Virginia has over 30 wineries across North, South, East, West trails and is home to some fantastic stops, and conveniently located near Charlottesville.

Courtesy of Barboursville Vineyards

Shenandoah Valley

Start the trip in Staunton and make your first stop the Natural Bridge, a must see site in Virginia. From here continue on to the towns of Lexington, Hot Springs and finish in Roanoke. Along the way there are history and culture stops with the Frontier Culture Museum, Woodrow Wilson Presidential Library and Museum, the American Shakespeare Center, Virginia Military Institute and Museum and Humpback Bridge, as well as battlefields and historical markers at every stop. You’ll also find interesting roadside eats along the way, plus good dining options in the towns. For a luxurious overnight, stay at the Homestead Resort. The Shenandoah Valley is really a beautiful part of Virginia and well worth the trip.

Natural Bridge, Virginia

Road Trip to Presidential Homes

Virginia has been the home of eight US Presidents, and most of their homes can be visited. Start just south of DC at Mount Vernon, the historic home of George Washington with ground tours, museums, and a working farm. From here go south to Richmond and stop at Berkeley Plantation, the birthplace of William Henry Harrison, and also Sherwood Forest, estate of John Tyler, to see where the ninth and 10th Presidents respectively grew up. A few minutes outside Richmond, you can visit Thomas Jefferson’s childhood home, Tuckahoe Plantation. Continue west to visit Jefferson’s crown jewel, Monticello, and further on to James Madison’s Montpelier. The landscape in this part of the state is gorgeous with mountain vistas around, wineries, and more. End the trip at Staunton, the birth place of Woodrow Wilson with a tour of the Presidential Library and insight into his early life.

Courtesy of

Culture Trips launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes places and communities so special.

Our immersive trips, led by Local Insiders, are once-in-a-lifetime experiences and an invitation to travel the world with like-minded explorers. Our Travel Experts are on hand to help you make perfect memories. All our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

All our travel guides are curated by the Culture Trip team working in tandem with local experts. From unique experiences to essential tips on how to make the most of your future travels, we’ve got you covered.

Culture Trip Spring Sale

Save up to $1,656 on our unique small-group trips! Limited spots.

Edit article