Hop On and Off this Virginia Road Trip Loop
Virginia is a state steeped in history, natural beauty, and charming towns, making it a perfect destination for a looped road trip. While this guide starts and ends in our picturesque town of Staunton, you can choose to start and end at any point on this journey. This road trip takes you through vibrant cities, historic landmarks, and breathtaking landscapes. Buckle up for an unforgettable adventure around the Old Dominion!
Staunton: The Starting Point
Nestled in the heart of the Shenandoah Valley, Staunton welcomes travelers with its quaint streets and rich cultural heritage. Be sure to explore the downtown area, where the past seamlessly blends with the present. The American Shakespeare Center and the Frontier Culture Museum provides a fascinating glimpse into history, setting the tone for your adventure. If you’re stopping here for the night, make sure you swing by The Blackburn for a peaceful night of relaxation on our beautiful property. Before you venture to Staunton, make sure you read our guide on the best things to do in Staunton.
Heading East: Charlottesville
Leaving Staunton, we head east to Charlottesville, a city known for its deep historical roots and vibrant arts scene. The drive through the rolling hills of Virginia is a treat in itself. In Charlottesville, you can tour Monticello, Thomas Jefferson’s iconic home, and wander through the charming pedestrian mall, sampling local delicacies and browsing unique shops.
Southbound: Richmond
The journey continues south to Richmond: Virginia’s capital. Here, history comes alive in the streets, from the Civil War monuments to the cobblestone streets of Shockoe Slip. Some local favorites include walking around the Virginia Museum of Fine Arts, or taking a leisurely stroll along the scenic Canal Walk. Richmond’s dynamic food scene will provide plenty of delicious dining options, from classic Southern fare to some innovative fusion cuisine. If you’re looking to stay here for a night, we would recommend staying at The Quirk!
Southeast: Williamsburg and the Historic Triangle
From Richmond, we’ll travel southeast to Williamsburg, immersing ourselves in the Colonial era. The Historic Triangle—comprising Williamsburg, Jamestown, and Yorktown—offers a deep dive into America’s early history. You can walk through the living-history museum of Colonial Williamsburg, visit the archaeological site of Jamestown, and explore the battlefield of Yorktown, where the American Revolution was won. For the thrill-seekers among you, you could also spend a day at the lively Busch Gardens theme park. If you love roller coasters, you’ll love Busch Gardens! Check out rides like Apollo’s Chariot, The Pantheon, or our favorite, The Griffon!
East: Norfolk and Virginia Beach
Heading further east, we reach the coastal cities of Norfolk and Virginia Beach. Norfolk, with its bustling waterfront and rich naval history, offers attractions like the Battleship Wisconsin and the vibrant NEON Arts District. A short drive away, Virginia Beach calls with its expansive sandy shores and lively boardwalk. Make sure you try the fresh seafood at local eateries, soak up the sun on the iconic beaches, and of course try a town-favorite Orange Crush!
Southwest: Roanoke and the Blue Ridge Parkway
Turning southwest, we headed towards Roanoke, a city surrounded by natural beauty. The drive along the Blue Ridge Parkway will be a highlight, with its stunning mountain vistas and numerous hiking trails. In Roanoke, you can discover the Taubman Museum of Art and enjoy the vibrant city market. The nearby Mill Mountain Star offers panoramic views of the Roanoke Valley, perfect for a scenic photo op. For a place to rest your head for the night, check out The Lofts at Downtown Salem, which offers renovated lofts available for the night, week, or month.
Northwest: Winchester and the Shenandoah Valley
This loop now brings us northwest to Winchester, a city with a rich Civil War history and a charming old town. Check out the Museum of the Shenandoah Valley and walk through the historic district, where 18th-century architecture abounds. The drive through the Shenandoah Valley, with its rolling landscapes and picturesque farms, will be a serene end to your journey.
Back to Staunton: Concluding the Loop
Returning to Staunton, we wrap up our adventure with a final stroll through downtown, then returning to The Blackburn. After spending so much time in a car, you’ll need a massage to get your muscles loose again. Visit The Spa at The Blackburn for your next spa treatment!
This loop around Virginia will be a journey through time and nature, from bustling cities to tranquil valleys, from historic landmarks to modern attractions. Each stop offers its own unique charm and story, making this road trip a truly enriching experience. If you’re looking to explore Virginia in all its glory, jump on this loop for the perfect itinerary!