12 Great Road Trips to Take in Virginia

For the most storied historic road trips, the Old Dominion of Virginia is a great state to relive much of the United States’ pre-independence past. But even if you’re more in the mood to enjoy some timeless natural scenery, Virginia also delivers on this front. From the tranquil beaches along the Chesapeake Bay to the mighty Blue Ridge Mountains, this Mid-Atlantic state abounds in unique land and seascapes visitors need to see to believe.

If you’re also hoping to gain cultural enrichment, you can find plenty of that on Virginia’s open roads. With everything from the country music heritage along the Crooked Road to the acclaimed wineries and craft breweries of Loudoun County, you can see, do, hear, and taste a lot as you make your way through Virginia. On this note, let’s check out these 12 incredible road trips to take in Virginia.

Arlington to Roanoke

If you intend to start your road trip in the Washington DC/Northern Virginia metro region, you might be surprised by how easy it is to make your great escape to the mountains. Running about 240 miles in total from Arlington, take the I-66 highway west to Front Royal, your “first stop to the Shenandoah Valley” that’s close to the north end of Shenandoah National Park, where you’ll find the Dickey Ridge Visitor Center and scenic stops like the Shenandoah Valley Overlook.

Continuing south from Front Royal, you can pass through Charlottesville or make a stop at Ivy Creek Natural Area to stretch out and enjoy seven miles of walking trails in a beautifully restored wildlife habitat where Ivy Creek meets the Rivanna River. If you want another rest stop where you can find some fresh local produce to try (or you need a place to park or camp), Sun Spoke Farms has everything from fresh fruit to ducks and goats greeting you on site. Finally, you’ll arrive in Roanoke, and you can head on over to The Hatch downtown for some of the region’s best homestyle Southern cuisine.

Richmond to Charlottesville

If you consider yourself a cultured oenophile, you might enjoy (with a designated sober driver) this epic 75-mile drive to one of Virginia’s premier wine country regions. Starting in the state capital of Richmond, head northwest on I-64. If you want to need a pit stop along the way, try Bracketts Farm near Gordonsville to learn about this special place that combines historic preservation with environmentally sustainable agriculture and community service.

Once you reach Charlottesville, check out Wineworks Extended for a taste of the prestigious Michael Shaps wines within easy reach, then head to Carter Mountain Orchard for the area’s highest tasting room (at 1,120 feet above sea level). To experience the new frontier in environmental preservation, book a tasting at Oakencroft and learn how they craft tasty and eco-conscious reds, whites, and rosés.

Virginia Beach to Jamestown

For an epic 70-mile journey from the Old Dominion’s biggest beach city to the place where British colonization of North America largely began, take this road trip north from Virginia Beach. Take I-64 or Highway 13 to I-64, then cross the Hampton Roads Bridge Tunnels to Hampton. While in Hampton, head to Fort Monroe National Monument to learn more about everything from the arrival of the first enslaved Africans to English North America at Point Comfort in 1619 to the establishment of the Civil War-era “Contraband Hospital” at this site where Harriet Tubman served as a nurse.

Continue north on I-64 to Williamsburg, then make your way to the Colonial Williamsburg to experience the world’s largest living history museum, a fully immersive recreation of 18th-century life in the Virginia colony where costumed interpreters guide you through iconic landmarks like the Governor’s Palace and the Peyton Randolph House, and where skilled artisans continue to craft incredible keepsake art. Meanwhile, at Historic Jamestown, see where the English colonists staked their claim in 1607 and where indigenous tribes led by Chief Powhatan fiercely fought to try to keep their land and communities intact.

Virginia Beach to Colonial Beach

For a more extensive coastal excursion, try this roughly 150-mile road trip from the Hampton Roads all the way up to the Northern Neck. As with the Williamsburg/Jamestown road trip, take I-64 north from the Norfolk/Virginia Beach area, but then take the Highway 17 exit at Newport News to see more of Virginia’s Chesapeake Bay coastline. Stop at Yorktown to enjoy an easy, breezy stop at Yorktown Beach, a lovely two-acre stretch of shoreline that’s good for swimming, fishing, and strolling. Later, travelers can head to the Watermen’s Museum to dive deep into the area’s rich maritime history. Or, if you're in the mood for more compelling history, go to the Yorktown Battlefield to see where America essentially won independence in 1781.

Keep heading north and cut off on Highway 3 to White Stone, a charming little town by the Rappahannock River, where one can see working art studios at the Allure Art Center and taste some hearty Chesapeake coastal cuisine at Willaby’s. Keep winding your way north to appreciate the unique scenery of the Northern Neck, and finish with a victory lap at Colonial Beach, where you can relax and kick back along the town’s two miles of sandy beaches and Potomac River waterfront. While you’re in the area, check out the George Washington Birthplace National Monument to see where the nation’s first president’s life journey began.

Mount Vernon to Great Falls

When you need a scenic road trip but can’t commit too much time to a long drive, you might want to opt for this easy 30-mile-long Washington D.C. area road trip that spans from Mount Vernon to Great Falls in Northern Virginia. Begin at George Washington’s Mount Vernon, the beloved family home of the nation’s first president and his spouse Martha, about 15 miles south of the United States Capitol. While at Mount Vernon, you can also tour the working gristmill and distillery (that offers summer whiskey tastings on Saturdays) and feast on contemporary interpretations of colonial-era cuisine at Mount Vernon Inn Restaurant.

Heading north, go to Old Town Alexandria to experience one of the DMV’s most beloved historic districts, where you can step back in time at landmarks like the Gadsby’s Tavern Museum and Carlyle House Historic Park. Continuing north to Arlington, road trippers can hit additional landmarks like Arlington National Cemetery, offering a look into the past. As you hop back onto the George Washington Memorial Parkway, you’ll want to go the distance and take the Georgetown Pike exit to reach Great Falls Park, a beautiful national park best known for its waterfall-rich stretch of the Potomac River.

Norfolk to Chincoteague

Starting from the storied maritime hub of Norfolk, this roughly 110-mile coastal journey will surely please beach and sea lovers. At Norfolk, visitors can begin their adventures at Nauticus, a unique museum and educational complex that includes everything from the historic Wisconsin battleship to a community sailing center. If you need a little beach time before you leave town, head to Ocean View Beach for a long and soothing stretch of sand.

Cross the famed Chesapeake Bay Bridge-Tunnel to reach the Eastern Shore, and stay on Highway 13 to discover more scenic beaches and special coastal finds. Stop at Kiptopeke State Park for swimming, kayaking, and fishing. For a different experience, one can try Savage Neck Dunes Natural Area Preserve, a 298-acre park with prime Chesapeake Bay beaches and maritime forest. If you need a food break, get delicious fresh catches at Metompkin Seafood in Mappsville. Finally, take Chincoteague Road to reach both the town and the National Wildlife Refuge, where you’ll find the world-renowned Chincoteague ponies, migratory bird habitats, and the pristine Atlantic shores of Assateague Island.

Roanoke to Bristol

Mountain lovers rejoice: This​​ epic 150+ mile expedition provides glorious Appalachian scenery, but it’s also rich in local culture and totally rad trad tunes. From Roanoke, make your way to I-81, then head south until you reach the Riner Road exit. Keep heading south on the highway to Floyd, a charming village with the legendary Floyd Country Store that’s home to the Friday Night Jamboree and other weekend country music performances. Wind your way southwest until you hit the town of Galax near the North Carolina state line, and look out for the Blue Ridge Music Center, a combination museum, cultural center, event venue, and nature preserve where bluegrass music flows as freely as the nearby mountain streams.

From Galax, hop onto Highway 58 and make your way west until you reach the town of Abingdon, then stop to explore hidden treasures like the historic Barter Theater, the official state theater of Virginia that’s entertained audiences since 1933. For a delectable diversion, head south a little more to reach Nicewonder Farm & Vineyards, a glorious working farm and boutique hotel with incredible farm-to-table fare at the Hickory restaurant. Finally, near the Tennessee state line, you’ll find Bristol, a lively city with a deep history of fostering homegrown country music talent: The Birthplace of Country Music takes you inside the 1927 Bristol Sessions that started it all, while the Paramount Center for the Arts lets you check out new and upcoming talent.

Richmond to Danville

At first glance, you might wonder what exactly is between the coast and the mountains. Yet on this 170-mile journey from the state capital south(west), you’ll uncover tranquil lakes, verdant forests, fascinating history, and so much more. Before you leave the Richmond area, stop at the Metro Richmond Zoo to see some 2,000 animals from some 190 species on 70 acres of an active wildlife conservation program. As you approach Farmville, stop at the Sandy River Reservoir for a pleasant fishing hole, or hit High Bridge Trail State Park for over 31 miles of protected lands for hiking, biking, and horseback riding.

Before departing Farmville, visit the Robert Russa Moton Museum to learn about how a local student strike in 1951 kickstarted the modern civil rights movement. Afterward, head south to Clarksville; it’s a very short hop to Occoneechee State Park, with over 20 miles of hiking and biking trails. From Clarksville, take Highway 58 west to Danville, where you will find everything from rare vintage military tanks at the AAF Tank Museum to gorgeous local art at the Danville Museum of Fine Arts and History.

Virginia Beach to Fredericksburg

When you’re seeking even more coastal fun and games, this roughly 200-mile-long journey from the Atlantic shoreline of Virginia Beach to the Potomac banks of Fredericksburg may be just what you need. Start at one of the last pristine expanses of the Atlantic Ocean coast at False Cape State Park, then go to First Landing State Park on the north end of Virginia Beach for over 20 miles of trails, large patches of cypress wetlands and maritime forest, and 1.5 miles of Chesapeake Bay beaches. From there, make your way to the Hampton Roads Bridge Tunnels and continue north to Newport News Park for a much-deserved break at one of the largest municipal parks east of the Mississippi, where you can enjoy everything from biking and hiking to canoeing, archery, disc golf, and fishing.

From Newport News, head north to Belle Isle State Park in Lancaster for seven scenic miles of shoreline along the Rappahannock River and a cool collection of farmland, upland forest, and tidal wetlands that animals like blue herons, bald eagles, white-tailed deer, and turkeys call home. Finally, make your way to Crow’s Nest Natural Area Preserve near Fredericksburg. This beautiful 3,000-acre expanse full of pristine riparian habitats and eight miles of hiking trails that let you explore a vast array of local terrain.

Richmond to Lynchburg via Vesuvius

Perhaps you remember that 1995 TLC song warning you not to chase Waterfalls. But for this roughly 225-mile road trip, it’s totally safe and encouraged to chase some incredible waterfall vistas! Starting in Richmond, head west towards Charlottesville. Stop at the James Monroe Highland estate if you need a quick break and a walk on the trails. Continue west until you reach Saint Mary’s Trail near Vesuvius, a moderate hiking trail that leads to a spectacular waterfall with swimming holes along the way. From Saint Mary’s Falls, it’s a fairly short drive through George Washington National Forest to reach Crabtree Falls: the highest vertical-drop cascading waterfall east of the Mississippi River, or a series of five cascades and multiple smaller falls that add to a total of 1,200 feet of drop.

As you go along Blue Ridge Parkway, look out for more incredible waterfalls, such as Statons Creek Falls and Panther Falls near Buena Vista. Continue south on Blue Ridge Parkway until you reach Apple Orchard Falls, a spectacular 200-foot cascade at Jefferson National Forest (near Buchanan). As you turn around to head back to Highway 501, enjoy equally impressive views of Apple Orchard and Terrapin Mountains, then head down to Lynchburg to reach Hollins Mill Park, a wonderful stretch of open space that includes the historic Hollins Mill Dam and waterfall.

Richmond to Assateague via Virginia Beach

Maybe you’re in more of an illuminating mood. For a truly enlightening 280-mile road trip from Richmond, head east and make your way to the New Point Comfort Natural Preserve in Mathews County. Not only does this preserve have an accessible boardwalk with lovely views of Mobjack Bay and the various migratory birds that fly through this area, but it’s also where you’ll find the Point Comfort Lighthouse, the second oldest light in the bay.

From Point Comfort, turn around, then head south to Virginia Beach. Stop at the Cape Henry Lighthouse, the United States government’s first federally funded public works project in 1792, and a beautiful expanse of coast where the Chesapeake Bay meets the Atlantic Ocean. Next, cross the Chesapeake Bay Bridge-Tunnel to reach Cape Charles, and take a quick detour to Cushman’s Landing to catch a glimpse of the Cape Charles Lighthouse. Finally, keep heading north and follow the signs to reach Assateague National Seashore, where you will discover the majestic 142-foot-tall Assateague Lighthouse that’s operated on the island since 1867.

Arlington to Lovettsville

Last but certainly not least, here’s one more road trip where you will need a designated driver, one (stretching for about 60 miles) leading from Arlington to Northern Virginia’s own wine country in Loudoun County. Once you reach Sterling, stop at Crooked Run Fermentation for their creative variety of house-made natural wines, craft beers, ciders, seltzers, and even New York-style pizza from J&J. Then, in Leesburg, hit Loudoun Brewing Co. for family-owned and hand-crafted beers.

Once you’re ready to see some real Loudoun wineries and breweries for yourself, hit Stone Tower Winery, Zephaniah Farm, and/or Casanel Vineyards just outside Leesburg for tours and tastings. Finish this amazing road trip with a visit to Hiddencroft Vineyards, an authentic Virginia farm winery in Lovettsville where almost all the wines (such as Petit Verdot, Chambourcin, and Traminette) are made with their own estate-grown grapes and where the tasting room is housed in an 1860s farmhouse.

Virginia Is for Road Trip Lovers

As they say, “Virginia is for lovers.” Suppose you like taking long and leisurely road trips. In that case, you may quickly fall in love with Virginia’s vast options for ambitious road trips, including adventures into the Shenandoah Valley, cool coastal drives around the Chesapeake Bay, and even a journey south of Richmond to discover hidden gems in Central Virginia. But even if you only have time for a shorter road trip, you still have great options, including a lovely drive through Alexandria’s and Arlington’s greatest landmarks and an easy ride from Hampton Roads to Chincoteague. No matter what best suits your taste, there are plenty of great road trips to take all around Virginia.