These 10 Epic Road Trips in Virginia Will Change Your Summer

Summer is the season for the open road. Windows down, music up, and no particular place to be.

Virginia is the perfect state for road trips, with mountains on one side, coast on the other, and everything in between. The ten trips on this list will change your summer.

Some follow the Blue Ridge Parkway, with views that make you pull over every few miles. Others wind through small towns where the main street looks like a postcard.

A few head to the coast, where you can feel the salt air before you see the water. I have driven every one of these routes, and each one left me wanting more.

Pack a bag, fill the tank, and pick a direction. Virginia is waiting.

1. Blue Ridge Parkway

There’s a reason people call this stretch of asphalt “America’s Favorite Drive,” and the moment you hit the first overlook, you’ll completely understand why.

The Blue Ridge Parkway cuts through roughly 105 miles of Virginia’s most jaw-dropping Appalachian scenery, and every single mile feels like a painting that hasn’t been finished yet.

The air smells different up here. Cleaner, cooler, like pine and possibility mixed together.

Humpback Rocks is my personal favorite stop along this route. The hike to the top is short but steep, and the payoff is a panoramic view that makes your phone camera feel completely inadequate.

Apple Orchard Falls is another must-stop, a cascading waterfall tucked into the forest that feels almost too beautiful to be real.

Summer mornings on the Parkway are genuinely magical. Mist rolls through the valleys below while the ridgeline glows gold in the early light.

Pull over at any of the designated overlooks and just sit for a moment. You won’t regret it.

The speed limit keeps things slow and intentional, which is honestly the whole point. This isn’t a drive you rush.

Pack a picnic, download an offline playlist, and plan to stop way more than you think you will. Wildflowers line the road in June and July, and the foliage turns absolutely electric by late summer.

Milepost 0 begins near Waynesboro, Virginia. Blue Ridge Parkway, Waynesboro, VA 22980.

2. Skyline Drive

Skyline Drive is the kind of road that makes you feel like the whole world shrunk down just for you. Running the entire spine of Shenandoah National Park for 105 miles, this National Scenic Byway offers more than 70 overlooks where you can stare out at rolling ridges that seem to go on forever.

I’ve driven it in every season, and summer hits different. The forest is so thick and green it practically glows.

Wildlife sightings here are basically guaranteed. White-tailed deer graze along the roadsides like they own the place, and if you’re lucky, you might spot a black bear lumbering through the tree line.

Bring binoculars. Seriously, don’t leave home without them on this one.

The drive starts at Front Royal in the north and ends near Waynesboro in the south. You can hop on or off at several entrance points, which makes it easy to customize your trip.

Most people spend a full day here, but a weekend lets you actually hike the side trails and breathe it all in properly.

Lodges and campgrounds inside the park mean you don’t have to rush back to civilization if you don’t want to. Falling asleep to mountain sounds after a day on Skyline Drive is an experience that city noise simply can’t compete with.

Skyline Drive is one of Virginia’s crown jewels, full stop. Shenandoah National Park, 3655 US-211 East, Luray, VA 22835.

3. Colonial Parkway

Driving the Colonial Parkway feels like slipping through a time portal, except the road is smooth and your air conditioning works perfectly. This 23-mile scenic route connects three of the most historically significant sites in the entire country: Jamestown, Colonial Williamsburg, and Yorktown.

That’s roughly 174 years of American colonial history, all stitched together by one beautifully maintained stretch of road.

The parkway itself is a work of art. Designed to blend naturally into the surrounding landscape, it has no commercial signage, no billboards, and no distractions.

Just trees, the occasional glimpse of the York River, and a quiet sense that something important happened here. It absolutely did.

Jamestown is where it all started, the first permanent English settlement in America. Colonial Williamsburg drops you into a living, breathing recreation of 18th-century colonial life.

Yorktown is where the Revolutionary War effectively ended, with a battlefield that still carries a certain weight in the air.

Summer is peak season here, so arriving early in the morning keeps the crowds manageable and the light gorgeous for photos. The speed limit is set low on purpose, encouraging you to slow down and actually look around.

This isn’t a drive you multitask through.

Kids and adults both find something to love here, which is rare and wonderful. Pack a lunch and plan a full day.

Colonial Parkway, Williamsburg, VA 23185.

4. The Crooked Road

Forget everything you think you know about a road trip playlist, because The Crooked Road will provide its own soundtrack. This 330-mile driving trail winds through the heart of Southwest Virginia’s Appalachian region, and it’s entirely dedicated to the mountain music that was born and raised in these hills.

Bluegrass, old-time, country, folk. All of it lives here, and it sounds best live.

Bristol, sitting right on the Virginia-Tennessee border, is considered the birthplace of country music, and the Birthplace of Country Music Museum does a spectacular job of telling that story. Galax is another essential stop, home to one of the oldest and largest old-time and bluegrass music festivals in the world.

The Rex Theater in Galax hosts live music most Friday nights, and the energy inside that room is something you simply can’t stream.

The towns along this route are small, proud, and genuinely welcoming. You’ll find luthiers still crafting fiddles and dulcimers by hand, front porch jams that start at sundown, and a pace of life that feels like a deep exhale after a long week.

The scenery isn’t exactly rough to look at either. Rolling mountains, old farmsteads, and winding two-lane roads make every mile a postcard.

Plan at least three days to do this route justice, and leave room for spontaneous stops.

The Crooked Road begins in Rocky Mount, Virginia. The Crooked Road, Rocky Mount, VA 24151.

5. Colonial Williamsburg to Presidential Homes Tour

Virginia has produced more U.S. presidents than any other state, and driving between their historic homes is one of the most unexpectedly fascinating road trips I’ve ever done.

The routes around Charlottesville and Northern Virginia connect you to the lives of founding fathers in a way that feels intimate and real, not dusty or textbook-dry.

Monticello, Thomas Jefferson’s stunning hilltop estate just outside Charlottesville, is worth an entire afternoon on its own. The architecture is breathtaking, the gardens are immaculately preserved, and the guided tours are genuinely illuminating.

George Washington’s Mount Vernon, perched above the Potomac River in Fairfax County, carries a completely different energy, more formal and commanding, which feels entirely appropriate.

James Madison’s Montpelier in Orange County is quieter and somehow more moving. The grounds have been carefully restored, and the story of the people who lived and worked there, both free and enslaved, is told with honesty and depth.

Each estate adds a new layer to the same complicated, fascinating American story.

The driving between these homes is genuinely lovely. Rolling Virginia countryside, tree-shaded back roads, and small towns with good coffee and better conversation make the journey as enjoyable as the destinations themselves.

This is the kind of road trip that makes you feel smarter by the end of it. Mount Vernon, 3200 Mount Vernon Memorial Hwy, Mount Vernon, VA 22121.

Monticello, 931 Thomas Jefferson Pkwy, Charlottesville, VA 22902.

6. Virginia’s Eastern Shore Drive

Most people drive straight past Virginia’s Eastern Shore on their way somewhere else, and honestly, that’s their loss. It’s accessible via the engineering marvel that is the Chesapeake Bay Bridge-Tunnel.

This sliver of land between the Chesapeake Bay and the Atlantic Ocean is one of the most underappreciated coastal stretches on the entire East Coast.

U.S. Route 13 is your guide, and it delivers.

Cape Charles is the kind of small town that stops you in your tracks. The Victorian architecture along its tree-lined streets is immaculately preserved, the waterfront is calm and gorgeous, and the whole place moves at a pace that feels like a weekend even on a Tuesday.

Kiptopeke State Park nearby offers coastal hiking trails with sweeping bay views that are genuinely hard to leave.

Chincoteague Island, at the northern end of the shore, is famous for its wild ponies, and yes, they really are roaming free on Assateague Island just across the bridge.

The Assateague Island National Seashore lighthouse stands tall against the sky, and the beaches here are wide, wild, and wonderfully uncrowded compared to the mainland options.

Crabbing, kayaking, and watching rockets launch from Wallops Island are all legitimate activities on this route. Pack light, bring sunscreen, and leave your schedule flexible.

The Eastern Shore rewards spontaneity like nowhere else in Virginia.

Start your drive at the Chesapeake Bay Bridge-Tunnel, 32386 Lankford Hwy, Cape Charles, VA 23310.

7. Route 11 Through the Shenandoah Valley

Long before the interstate came along and swallowed up the traffic, Route 11 was the main artery of the Shenandoah Valley, and it’s still the best way to actually see it.

Known as the Valley Pike, this old road threads through Winchester, Strasburg, Woodstock, New Market, Harrisonburg, Staunton, and Lexington, each town with its own personality and its own reasons to stop.

Winchester in the north is a charming city with a walkable downtown and deep Civil War history. Luray, just a short detour east, is home to Luray Caverns, where underground chambers full of massive stalactites and stalagmites will make your jaw drop completely.

The caverns stay cool year-round, which is a very welcome bonus on a hot summer drive.

Lexington, near the southern end of the valley, might be the most beautiful small city in Virginia. Washington and Lee University and Virginia Military Institute sit side by side on a hill, their historic buildings framed by the mountains in every direction.

The downtown is full of independent shops, great coffee spots, and a genuinely welcoming vibe.

The farmland between towns is spectacular. Cattle graze in fields backed by mountain ridgelines, old barns lean picturesquely into the wind, and the sky seems bigger here than anywhere else.

This route rewards slow driving and curious detours. Route 11, Shenandoah Valley, VA.

Start near Winchester, VA 22601.

8. Virginia Wine Trail and Monticello Wine Region

Virginia has been quietly building one of the most exciting wine regions on the East Coast, and the Monticello Wine Trail near Charlottesville is the crown jewel of the whole operation. Driving through this area in summer is a genuinely sensory experience.

Rows of grapevines stretch across rolling hills with the Blue Ridge Mountains stacked up in the background like a postcard that never gets old.

The Monticello American Viticultural Area covers a significant stretch of Albemarle County. The landscape between each stop is so lovely that the drive itself earns its place on the itinerary.

Charlottesville serves as a perfect base for this trip. The downtown pedestrian mall is one of the best in Virginia, lined with independent restaurants, bookshops, and live music venues.

After a day of winery-hopping through the countryside, an evening on the mall feels like the ideal landing spot.

Late summer is peak season for this route. The vines are full and green, the light is warm and long, and the whole region seems to hum with a relaxed, celebratory energy.

Go on a weekday if you want a more personal experience at each stop.

Start your wine trail exploration at the Charlottesville Visitor Center, 610 E Main St, Charlottesville, VA 22902.

9. Route 58 Cradle of Racing Drive

Route 58 is Virginia’s longest state highway, stretching a full 511 miles from the sandy shores of Virginia Beach all the way to the Cumberland Gap in the far southwest corner of the state. That’s a serious road trip, and it passes through enough variety of landscape, culture, and history to fill an entire travel memoir.

I’ve driven sections of it multiple times and still find new things to love.

The eastern end starts at the Atlantic Ocean, which is a pretty dramatic opening act. Virginia Beach fades into the flat, agricultural plains of Southside Virginia, where the pace slows and the sky opens up wide.

Small towns like Emporia and South Hill have a quiet charm that rewards a stop and a slow walk around.

For motorsports fans, the middle section of this route is electric. South Boston Speedway in Halifax County has been a beloved short track racing venue for decades, and the Virginia International Raceway near Alton is one of the most respected road courses in the country.

Even if racing isn’t your thing, the energy around these places on event weekends is infectious.

The western end of Route 58 climbs into the mountains, passing through Martinsville, Galax, and eventually reaching the Cumberland Gap, where Virginia, Kentucky, and Tennessee all meet at once. That last stretch alone is worth the entire drive.

US-58, Virginia Beach, VA 23451 to Cumberland Gap, VA 24219.

10. Alleghany Highlands Loop

Few road trips in the entire mid-Atlantic region pack as much outdoor adventure into a single loop as the Alleghany Highlands route through Bath and Alleghany counties in western Virginia. This is the kind of drive that attracts people who want more than a view from a car window.

They want to get out, get moving, and get genuinely wild for a few days.

Falling Spring Falls is one of the most dramatic natural sights on the entire route. The waterfall drops a stunning distance over a rocky cliff face, and you can view it easily from the roadside pullout on US-220, which means even a quick stop delivers maximum impact.

For a longer adventure, kayaking the Jackson River through a scenic gorge is absolutely unforgettable. The water is clear, the canyon walls are gorgeous, and the whole experience feels miles removed from ordinary life.

Lake Moomaw, tucked into the mountains of Bath County, is a reservoir so clean and blue it looks almost unreal. Swimming, fishing, and paddling are all popular here in summer, and the surrounding forest keeps temperatures noticeably cooler than the surrounding lowlands.

Warm Springs, the tiny county seat of Bath County, has a charming historic district and the famous Warm Springs Pools, natural thermal pools that have been welcoming visitors for centuries. The whole loop takes two to three days done properly.

Alleghany Highlands, Bath County, VA. Start near Warm Springs, VA 24484.