U.S. Route 58 in Damascus, via Metayel on Wikipedia

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 Historic District in Virginia
Chilhowie Historic District in Virginia, By James Shelton32 - I photographed the downtown Chilhowie Historic District., CC BY-SA 3.0, Wikimedia Commons

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.  


Beautiful historical buildings in Virginia Tech University in Blacksburg, Virginia
Beautiful historical buildings in Virginia Tech University in Blacksburg, Virginia

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. 


Street view in Damascus, Virginia
Street view in Damascus, Virginia. Image credit: Joe via Flickr.com.

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. 


The ancient Elk Run Dunkard Meeting House in Luray, Virginia.
The ancient Elk Run Dunkard Meeting House in Luray, Virginia. Editorial credit: christianthiel.net / Shutterstock.com

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. 


Main street in Chincoteague, Virginia
Main street in Chincoteague, Virginia, via Kosoff / Shutterstock.com

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." 


The Red Fox Inn and Tavern in Middleburg, Virginia, USA.
The Red Fox Inn and Tavern in Middleburg, Virginia, USA. Editorial credit: Nigel Jarvis / Shutterstock.com

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 houses built among Virginia's picturesque vineyards, the well-heeled town may be tough to afford, but visiting is far less expensive. Middleburg's quirky personality shows mostly through an odd claim to fame: the place thinks of itself as 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 mark 300 years of business. For some reading material and a one-of-a-kind book collection, visit the Middleburg's National Sporting Library, dedicated (again) to horse-related sports. The site is building a museum and a gallery for — what else? — horse-themed art. 


Downtown Culpeper, Virginia.
Downtown Culpeper, Virginia.

Culpeper, population 20,800, brings small-town charm together with the attractions of nearby Washington, D.C. Culpeper can trace its layout to a teenage surveyor and Virginia native: the future first president, George Washington. Later history would come in the form of the Battle of Cedar Mountain, a Civil War battle from 1862, located nearby in Culpeper County. The town has almost 30 NRHP sites.

Culpeper likewise has a number of odd, or just plain interesting, histories. During the Cold War with the Soviet Union, the town once held a "Federal Reserve bunker" to help safeguard the US dollar currency in case of attack. Today, the town's National Audio-Visual Conservation Center, a part of the Library of Congress, preserves US broadcast, video, and related recordings. The site houses more than 6 million artifacts across film, television, and sound media.

Virginia Has Quirks For All Travelers

As these towns show, Virginia's quirks only add to its charms for travelers. Damascus offers enough hiking trails for a lifetime of exercise. Chincoteague offers a strange but true story of stray horses. Middleburg takes horse culture to new levels. And from oddly named towns like Chilhowie, which harbor fascinating frontier history, to the legacies of hit TV shows and other media like those found in Luray and Culpeper, Virginia's place among the quirky, and the quintessential, of America's cultures make the state a must-see. Virginia's legacies combine the odd and the authentic — making the place one to visit in all seasons. 

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