From spring blooms and summer greens to the brilliant oranges and reds of fall foliage, a drive through the state’s colorful countryside offers opportunity for unforgettable Virginia vacation memories no matter the season. What makes Virginia even more special, though, is how the entire state overflows with historical significance.
A drive through the state allows you to, in a way, relive important moments in American history as you venture through the scenery that was its backdrop.
Here is a multi-stop itinerary across Virginia that will bring you to sites and cities that expose you to centuries of American history.
Start: Virginia Beach
Known for its white sand beach and three-mile resort-lined boardwalk, Virginia Beach has even more to see once you get off the beaten track. Take the historic village of Pungo, for example.
Centered in the Virginia Beach farming belt, Pungo is where you can indulge your taste buds at the annual Strawberry Festival on Memorial Day Weekend or sip blueberry honey wine.
Fuel your body for your road trip at The Bee and Biscuit in historic Pungo Village. Pair French press-style coffee with freshly made orange zest biscuits drizzled with honey and locally sourced bacon and eggs. For an even heartier meal, opt for the Dirty Hippy Breakfast Burrito made with black beans and avocado with a side of lime cilantro dressing.
Destination 1: Richmond, Virginia
From Virginia Beach: 116 miles, 2 hour drive time
Along the Way
The route follows the General Mahone Highway, a Civil War route used by the Confederate Army, through the green countryside. Stands of loblolly pines tower above native sugar maples that blaze shades of orange and crimson in autumn. Stop at Wakefield Peanut Company in Wakefield, Virginia, to stretch your legs and savor gourmet Virginia peanuts and other treats.
In Chester, stop at Ashton Creek Vineyard for local wine, cider, cheese and jam. Linger in the tasting room and enjoy savory treats like conch fritters, duck dumplings or garlic asiago potato frites.
Welcome to Richmond
As the state’s capital, Richmond brims with historic sites. Thomas Jefferson partly designed the capitol building, drawing his inspiration from the Maison Carrée temple in France. Join a free guided tour of the building Monday through Saturday during business hours or on Sunday afternoons. Or sit in on a session of the oldest legislative body in the Western Hemisphere.
Check out the collection of sites that comprise the American Civil War Museum on your road trip. Richmond’s downtown riverfront hosts Historic Tredegar, a towering brick iron works that produced more than 1,000 cannons for the Confederacy.
Marvel at the giant waterwheel that provided power for the factory, old Confederate currency and other relics from the era. While you’re there, visit the Richmond National Battlefield and stroll tree-lined trails winding through Civil War battlefields.
After, head to the White House and Museum of the Confederacy, a Federal-style mansion that was home to President of the Confederate States of America, Jefferson Davis. The museum sits in the historic Court End neighborhood which is rich in 19th-century Neoclassical and Federal architecture.
Destination 2: Monticello in Charlottesville, Virginia
From Richmond: 72 miles, 1 hour and 15 minute drive time
Along the Way
Dense hardwood forest flanks the highway as you travel toward Charlottesville, coming alive with russet shades in autumn months. If you care to meander, take Highway 250 which follows parallel to I-64. The side highway takes you off the beaten track through Gum Spring, a pre-Civil War freed-slave settlement that was home to one of the earliest post-war freedman’s schools.
Pick fresh blackberries and tomatoes in summer at the Newcastle Bee and Berry Farm in Louisa, Virginia. The farm has year-round crops you can gather yourself, including winter kale, fall pumpkins and springtime strawberries and asparagus.
Welcome to Charlottesville
Visit Thomas Jefferson’s famous self-designed plantation, Monticello in Charlottesville. Jefferson grew 330 types of vegetables, 170 varieties of fruit and 160 species of trees and flowers on the grounds.
While you’re there, you can buy more than 90 varieties of heirloom herb and vegetable seeds. Estate-inspired gifts, such as reproductions of Jefferson’s Monticello Obelisk Clock and 19th century-style home accents, are also for sale on-site.
Jefferson was a key figure in Virginia’s early wine industry, growing exceptional varietals. Visit Blenheim Vineyards to experience Cabernet Franc, Petit Verdot, Cabernet Sauvignon and other varietals. Sip vintages in the timber-framed tasting room where you can look through the glass floors into the tank and barrel floor.
Destination 3: Winchester, Virginia
From Charlottesville: 149 miles, 3.5 hour drive time
Along the Way
Roll through Shenandoah National Park along one of the country’s most scenic leaf-peeping road trips. More than 100 miles of uninterrupted foliage peaks in October when maples, sassafras, hickories, oaks and other colorful foliage erupt in vibrant shades of red, yellow and orange.
Skyline Drive slices 105 miles through the Blue Ridge Mountains as it passes through the park. Pull off at one of 75 overlooks to take a scenic selfie or just gaze at the stunning view of seemingly endless layers of forested hills. Stop at Luray Caverns to stroll along well-lit pathways through the country’s largest, most scenic caverns. Tours run every 20 minutes.
Welcome to Winchester
From Civil War battlefields to luxurious plantation homes, Winchester rolls out days of sightseeing to delight the history buff. Visit the 18th-century Abram’s Delight, a state-of-the-art luxury home for its time.
Discover period furnishings and antiques that swaddled the owners in the finest comfort of the day. But not everyone lived in this fashion in Winchester. Check out a restored log cabin onsite and see the simple lifestyle that was the norm for the area during this era.
If you have a few days, you’ll find a host of historic sites to visit in the area. Explore the expansive Museum of the Shenandoah Valley to discover four regional art galleries, 6 acres of formal gardens, and one of the largest private decorative art collections contained in an 18th-century home.
Destination 4: Harper’s Ferry, West Virginia
From Winchester: 30 miles, 39 minute drive time
Along the Way
Get out and stretch your legs at Potomac Gorge’s Billy Goat Trail. The three sections of trail yield exceptional views overlooking the Potomac River. Choose the trail segment that best suits your hiking ability.
To challenge yourself, opt for the strenuous Section A starting just below Great Falls. For the easiest hike, Section C offers relatively smooth trail ideal for viewing spring wildflowers or fall foliage. Download the self-guided audio tour from the Nature Conservancy to get the most enjoyment as you encounter rare plant life and scenic views along the legendary river. Without it, how would you ever recognize a Sigafoos tree?
Welcome to Harper’s Ferry
Visit Harper’s Ferry National Historic Park at the confluence of the Shenandoah and Potomac Rivers. More than just a scenic place that Thomas Jefferson described as “worth a voyage across the Atlantic for,” it was the site of a national armory and transportation hub that changed hands 14 times during the Civil War.
It’s not hard to imagine life in the 1850s when you stroll the trails through dense forest that looks much the same today as it did then. Follow the trails to Civil War skirmish lines or scenic overlooks. Dive even deeper into the 19th century by taking a historic trade workshop where you can learn what it takes took to become a blacksmith or candy maker.
Destination 5: Washington, D.C.
From Harper’s Ferry: 67 miles, 1 hour and 15 minutes drive time
Along the Way
Before heading into the nation’s capital, there’s one more stop you won’t want to miss. Best Farm is the historic site of the Monocacy National Battlefield in Maryland. Eighteenth-century stone buildings sit on 274 acres of green farmland, unscathed by the Civil War battle that took place on its grounds.
Welcome to Washington, D.C.
Visit a host of free historic attractions in Washington, D.C. From the massive Washington National Cathedral to the National Zoo, you’ll find dozens of things to do that won’t dent your vacation budget. While you’re there, don’t miss the Tidal Basin.
The 2-mile pond erupts with cherry tree blossoms in springtime. Walk around the pond on a trail or rent a paddle boat to see the blossoms from the unique perspective of the water.
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