Road Trip from Washington, DC, through Virginia’s Cities and Towns

A historic state that combines aspects of both the Southeastern and Northeastern USA, Virginia blends the South’s famously gracious hospitality with the bustling attractions of Washington, DC, and beyond.

Fly into Washington Dulles International Airport (IAD) and, after you’ve checked off DC’s iconic monuments and memorials, pick up a rental car for a journey through the history and natural beauty of Virginia.

Arlington, Virginia: National History and Local Flavor Near DC

ArlingtonVirginia, is the ultimate for attractions, convenience and value in the Capital Region. Explore its walkable neighborhoods and numerous famous landmarks, while taking advantage of lower hotel rates, all just minutes from DC’s attractions. Notable sites include the Marine Corps War Memorial (the “Iwo Jima” statue), National 9/11 Pentagon Memorial, Air Force Memorial and the impressive Arlington National Cemetery, where you can witness the Changing of the Guard at the Tomb of the Unknown Soldier. Bike on the Mount Vernon Bike Trail, a 27-kilometer path along the Potomac that ends at George Washington’s Mount Vernon. Watch for jaw-dropping fly-overs from Reagan National Airport. Go shopping in Shirlington and Pentagon City, savor dinner al fresco in Rosslyn and close down the bars in nightlife-loving Clarendon. Enjoy the value rates at one of 45 hotels before heading to Loudoun County, your next destination.

Loudoun County: Wine Country and Ale Trail Touring

Arlington to Loudoun: 80 km, 1 hour by car

DC’s Wine Country, Loudoun County, is just ahead, but first, stop by Great Falls Park, where the rushing water of the Potomac River cascades over dramatic rock formations. Once in Loudoun County, park the rental car for the day and hop on a guided tour of the area’s lush wineries and cool craft breweries with one of the many local tour and transportation companies. Voted Virginia’s favorite winery four years in a row, family-owned Breaux Vineyards pours award-winning wines alongside awe-inspiring views of the Blue Ridge Mountains. Beer lovers can follow the LoCo Ale Trail to discover more than 20 craft breweries such as Dirt Farm Brewing, a “plow to pint” farm brewery that grows its hops on-site. In addition to artisan drinks, Loudoun County offers Civil War historic sites, horseback riding, farm-to-table dining and charming towns such as Middleburg in the heart of hunt country to thriving downtowns such as Leesburg, the county seat. Continuing on your road trip, Staunton is up next.

Staunton: A Taste of Shakespeare in a Mountain Valley

Loudoun to Staunton: 201 km, 2 hours by car

Halfway to Staunton, make a stop at Luray Caverns, the largest series of caverns on the East Coast. Don’t miss a musical performance on the Great Stalacpipe Organ, the world’s largest musical instrument. While it may be small, the town of Staunton’s downtown revitalization, outstanding cultural scene and oh-so-adorable Main Street has been lauded by Architectural Digest, Travel + Leisure, Smithsonian and USA Today. Catch a performance at the American Shakespeare Center’s Blackfriars Playhouse, the only re-creation of Shakespeare’s indoor theater in the world. It’s one of Staunton’s biggest claims to fame and a true can’t-miss when you visit. Download the Traipse app for a self-guided, scavenger-hunt-meets-history-lesson tour of the city’s six historic districts and beautiful architecture (with the added bonus of unlocking discounts to locally owned businesses). Find cozy downtown accommodations before heading to Charlottesville.

Charlottesville: Monticello and So Much More

Staunton to Charlottesville: 64 km, 0.75 hours by car

The Blue Ridge Parkway intersects with the route to Charlottesville. If your itinerary allows, it’s worth the detour into Shenandoah National Park to experience one of the most scenic drives in the USA. In Charlottesville and surrounding Albemarle County, rich history and a nationally acclaimed culinary scene are on the agenda. The destination is home to Thomas Jefferson’s Monticello, a UNESCO World Heritage Site. Plan for a tour of the historic home and gardens of one of the Founding Fathers and the third President of the United States. Head to the historic Downtown Mall, where you can soak up the weather at an outdoor café, listen to live music (Dave Matthews Band started here), peruse art galleries and shop for souvenirs. Use the free trolley to get around downtown and visit the stately grounds of the historic University of Virginia, also a UNESCO World Heritage Site. Richmond, your final stop, is next.

Richmond: New Trends in the Old South

Charlottesville to Richmond: 116 km, 1.25 hours by car

Take scenic Route 250, dotted with small towns and peaceful scenery, into Richmond, Virginia’s state capital and a progressive cultural center offering rich history against a vibrant backdrop. Whether you’re into outdoor adventure, art, history, world-class dining, shopping or nightlife, Richmond has it all. Museums and historic sites including the American Civil War Museum, Virginia State Capitol and circa-1741 St. John’s Episcopal Church tell the story of Richmond’s prominent role in U.S. history. Get your heart pumping with a whitewater rafting trip on the James River – the Class III and IV rapids run right through downtown – or keep it low-key with a bike ride and picnic on the rocks along the river at Belle Isle. Meander through Richmond’s diverse neighborhoods such as Carytown, great for boutique shopping and nightlife along the aptly nicknamed “Mile of Style,” or the Fan District (named for its fan-like shape) with charming row houses and corner restaurants. Head to the Arts District for all things creative: art galleries, record shops, theaters, funky fashion boutiques, rooftop cocktail bars and trendy eateries – think hyper-local hummus and craft charcuterie. Spend the night in Richmond to allow yourself time to take it all in before driving around two hours back to Washington Dulles airport for your flight home.