7 of the Quirkiest Towns in Virginia

Virginia is thought of as a place of quaint culture and exceptional natural beauty. But the state's character has a quirky side, too. From eccentric characters and strange-but-true stories, the state offers a wealth of tales and experiences that a visitor needs to see and do to believe. With a heritage combining frontier drama, Civil War history, and a place somewhere between the Mid-Atlantic and the American South, Viriginia's strange place in US history and culture can be found nowhere else. The towns here illustrate Virginia's odd, and often amazing, attractions for travelers. 

Chilhowie

Chilhowie, population a modest 1,600, is located in Virginia's southwest corner, just above the horizontal state borders with Tennessee and North Carolina. European settlers were present here from the 1740s. The town's quirky name derives from a word in the Cherokee Native American language meaning "Valley of many deer." The town's other unusual features include the fact it only has one traffic light. The town onced served as the base for "longhunters," or men heading out on long-term hunting expeditions, where hunters might disappear into the Appalachian woods for months at a time.

Eccentrics like these helped shape Chilhowie as well as the colonial American frontier, given their depth of knowledge and fact-finding about inaccessible parts of the surrounding wilderness west of town. The territories they explored would later become the states of Kentucky and Tennessee.  

Blacksburg

Blacksburg, a larger southwest town with 45,600 inhabitants, sits among the beloved Blue Ridge Mountain range. Home to the Virginia Polytechnic Institute and State University — better known as Virginia Tech. Blacksburg has welcomed engineering students, quirky or more normal, since 1872.

Nature enthusiasts will appreciate the town's scenic trails in Jefferson National Forest, especially during fall leaf-changing season. McAfee Knob, rising nearby, is considered the most photographed point along the Appalachian Trail, the premier American hiking route that goes from Georgia to Maine.  The Huckleberry Trail, a rail bed converted for cycling and other sports, takes its name from the local vegetation. Former train travelers along the line, then owned by the Virginia Anthracite Coal and Railway Company, used to endure so many breakdowns and service delays, they passed the time picking huckleberries along the way. 

Damascus

The southern town of Damascus, with only 800 inhabitants, could use a few more companions, which may be why it is called the "Friendliest Town on the Trail." That slogan refers to its position on the Appalachian Trail, another local attraction.

The town also goes by the name "Trail Town USA," with four separate hiking paths: aside from the Appalachian Trail, Damascus also sees traffic from US Bicycle Route 76, the Iron Mountain Trail, and the Virginia Creeper Trail. For some social life and a little lunch, hikers usually head to the Damascus Diner or Mojo's Trailside Cafe. Damascus also sits near the Daniel Boone Heritage Trail, named after the iconic American "longhunter" and frontiersman, as well as near the Crooked Road Music Heritage Trail, meant to commemorate the region's rich folk and bluegrass music cultures. 

Luray

Luray, with 4,800 souls, sits in Virginia’s picture-perfect Shenandoah Valley. Full of natural beauty, the town is located not far from Shenandoah National Park and the George Washington National Forest. Luray Caverns is a popular visit for Virginia school field trips, for its underground geological formations of stalactites and stalagmites, is a great family travel destination.

The grounds sit just next to another local oddity: the Luray Singing Tower, a belltower built in 1937. The building holds 47 bells — the largest weighing more than 7,600 pounds. The site puts on free "carillon" (bell music) concerts in every season but winter. Other strange, wonderful sites in town include Cooter's Place, a museum dedicated to the TV show "Dukes of Hazzard" and owned by a former cast member. 

Chincoteague

Chincoteague, population 3,300, blends beauty with a strange and unique local wildlife. Found along the barrier islands of the Delmarva Peninsula, the town celebrates the natural and human histories of the Chesapeake Bay — one of the world's largest estuaries. For the full local story, check out the Museum of Chincoteague Island in town. The region's natural abundance is protected within the nearby Chincoteague National Wildlife Refuge. 

Chincoteague is perhaps best-known for its local species of wild horse, known as the Chincoteague pony. The horses are said to be the relatives of Spanish animals that were shipwrecked in colonial times adapted to the seaside environment. Local horse riders and ranchers are known as "saltwater cowboys." 

Middleburg

With a mere 700 residents, the small town of Middleburg, west of Washington, DC, is not a village on the verge of disappearing—it is actually one of Virginia's most expensive places. The town is so classy that John and Jacqueline Kennedy used to vacation there. With dream homes built among Virginia's picturesque vineyards, this affluent town may be tough to afford, but visiting is far less expensive. Middleburg's quirky personality mainly shines through an odd claim to fame: the place considers itself America's "horse and hunt capital," with regular events in steeplechase, foxhunting, polo, and other horse-based pastimes. The town's historic district is listed on the National Register of Historic Places (NRHP). In 2028, the local Red Fox Inn and Tavern will celebrate 300 years in business. For some reading material and a one-of-a-kind book collection, visit Middleburg's National Sporting Library, dedicated (once again) to horse-related sports. The site is developing a museum and a gallery for—what else?—horse-themed art. 

Culpeper

Culpeper, with a population of 20,800, combines small-town charm with the attractions of nearby Washington, D.C. The town can trace its layout back to a teenage surveyor and Virginia native: the future first president, George Washington. Its later history includes the Battle of Cedar Mountain, a Civil War battle from 1862, which took place nearby in Culpeper County. The town is home to nearly 30 NRHP sites.

Culpeper also features a number of peculiar, or simply intriguing, histories. During the Cold War with the Soviet Union, the town once housed a "Federal Reserve bunker" to help protect the US dollar currency in case of an attack. Today, the National Audio-Visual Conservation Center, part of the Library of Congress, preserves US broadcasts, video, and related recordings. The site holds over 6 million artifacts across film, television, and sound media.

Virginia Has Quirks For All Travelers

Virginia's unique qualities enhance its appeal to travelers. Damascus boasts a lifetime's worth of hiking trails. Chincoteague has an unusual but true tale of wild horses. Middleburg elevates equestrian culture. From intriguingly named towns like Chilhowie, rich in fascinating frontier history, to the influences of popular television shows and other media found in Luray and Culpeper, Virginia's blend of the quirky and quintessential aspects of American culture makes it a destination that cannot be missed. The state’s heritage merges the unusual with the authentic, inviting visitors throughout the year.