The Strangest Road Names in Virginia and How They Got Them
Virginia’s landscape is dotted not only with mountains and colonial landmarks but also with road names that tell quirky stories of its past and people. Just outside Richmond, in Henrico County, lies a stretch known as Three Chopt Road. This historic route, about 20 minutes west of downtown Richmond, traces back to a colonial-era trail used for chopping three trees to mark a path through dense wilderness. Walking or biking along the adjacent Three Chopt Trail Park offers a tangible connection to this past, as the park’s wooded paths echo the rugged frontier spirit that inspired the road’s name. Visiting in early fall reveals vibrant foliage that paints the landscape in reds and golds, making it a perfect time to reflect on the roots of this strangely named thoroughfare.
Head southwest of Roanoke, about 15 minutes from the city center, to explore the Blue Ridge Parkway near the Peaks of Otter. Here, you’ll find the oddly named Crabtree Falls Road, leading to one of the tallest cascading waterfalls east of the Mississippi. The name “Crabtree” might sound like it references a crustacean, but it actually honors a local family from the 18th century. Hiking the 2.5-mile loop trail at Crabtree Falls immerses visitors in lush forest and misty waterfall views, providing a dramatic backdrop to the peculiar name on the road signs. Early spring, when wildflowers bloom alongside the trail, offers the most enchanting experience, enhancing the mystery behind the road’s unusual moniker.
In the heart of Williamsburg, about two hours southeast of Richmond, visitors encounter the famously named Quarterpath Road. This road dates back to the Revolutionary War, its name stemming from a literal “quarter path” soldiers used as a shortcut between encampments. Today, the Quarterpath Trail follows a segment of this historic route, threading through woodland and marshland near the historic Colonial Parkway. Walking here in the crisp, quiet mornings of late spring connects travelers with centuries of military history embedded in the land, making the road’s name feel like a living narrative rather than just a quirky label.
Traveling to Virginia’s Eastern Shore near Chincoteague Island, roughly three hours east of Norfolk, you’ll find Maddox Boulevard—a name that might seem straightforward but is tied to local lore. Maddox Boulevard runs through the Chincoteague National Wildlife Refuge, a prime spot for wildlife viewing and birdwatching. The name honors early settlers who helped tame this coastal land, but today, the road leads visitors to wildlife trails and salt marsh overlooks where one might glimpse the famous wild ponies of Assateague. Visiting in late summer, when the ponies are often gathered for the annual roundup, adds a layer of cultural richness to this oddly named coastal route.
Out west near the Shenandoah Valley, just a half-hour drive from Harrisonburg, there’s the intriguingly named “Gap Road,” which crosses through the George Washington National Forest. This road earns its name from traversing mountain gaps and ridges along the edge of the forest. The nearby Stony Man Trail, accessible from Skyline Drive, climbs to one of the highest peaks in Shenandoah National Park. The rugged terrain and sweeping views of the valley below make it easy to imagine why early settlers named their passage after the natural gaps they had to navigate. Visiting in autumn, when the park’s famous fall colors blaze across the hillsides, presents a stunning scene that matches the road’s rugged essence.
In Alexandria, just across the Potomac from Washington, D.C., King Street stands as a main artery with a name that might seem ordinary but carries a royal legacy. The street cuts through Old Town Alexandria, a historic district filled with colonial-era architecture, cobblestone sidewalks, and vibrant waterfront views. King Street was so named to honor King Charles II during the city’s founding. Strolling this thoroughfare at dusk, when the sun sets over the Potomac, reveals how the name and place intertwine—a regal path through a city that has witnessed centuries of American history unfold.
Farther south in Lynchburg, about two hours southwest of Richmond, lies the quirky Black Dog Trail. The road name traces to a local legend about a mysterious black dog that haunted the nearby countryside. This rural route leads toward the scenic Blackwater Creek Natural Area, where hiking trails wind through forested valleys filled with wildflowers and songbirds. Walking Black Dog Trail in the cool dawn hours, when mist rises from the creek, heightens the eerie yet beautiful feeling that gave rise to the road’s strange name, inviting visitors to delve into local folklore amid nature.
Finally, near the quaint town of Abingdon in southwestern Virginia, you’ll find the curious “Paint Lick Road.” About 20 minutes from Abingdon, this road runs near a stream historically named for the reddish clay deposits used by Native Americans for body paint and pottery. The nearby Virginia Creeper Trail, a converted rail trail famed for its gentle grades and scenic views, crosses near this road. Biking or hiking along the trail in spring, when wildflowers carpet the valley, reveals a landscape deeply connected to indigenous culture and natural resources, giving new meaning to the unusual road name you might otherwise overlook.
Each of these roads offers more than a name—they provide a doorway into Virginia’s layered past and vibrant present. By visiting places like Three Chopt Trail, Crabtree Falls, and the quarterpath near Williamsburg, travelers can unravel the stories behind the strange, sometimes mystifying names that dot the Virginia map. These roads invite exploration not just of geography, but of history, legend, and the natural world that shaped the Old Dominion’s unique character.