Aerial view of Fredericksburg, Virginia.

13 Most Underrated Towns In Virginia To Take A Trip To

Invigorating natural beauty, rich historical heritage, delightful Southern charm - you can quickly run out of superlatives to describe this lovely East Coast destination. Virginia is steeped in American history, being one of the original 13 colonies, with numerous Civil War landmarks and Revolutionary War relics spread throughout its expanse. Diverse natural landscapes, from the Chesapeake Bay and the Atlantic Ocean to the Appalachian Mountains, give the Old Dominion unique charisma. 

While big cities like Virginia Beach and Richmond often steal the spotlight, the small, overlooked towns genuinely are the heart and soul of the state. Each comes with a unique personality, distinct attractions, and friendly communities where you can experience trademark Southern charm. Whether a history fanatic, culture connoisseur, or ardent adventurer, these are the most underrated towns in Virginia to visit. 


Historic Grist Mill in Abingdon, Virginia.
Historic Grist Mill in Abingdon, Virginia.

This Washington County town embodies the rich history and natural beauty synonymous with Virginia’s countryside. Home to a modest population of about 8,500, it harbors a treasure trove of iconic landmarks in its Historic District. Walking along the 20-block stretch of ancient structures is a unique experience that allows you to explore notable venues like the William King Museum of Art and the Fields Penn 1860 Museum. There are also numerous antique shops in Abingdon, and you can roam the downtown corridor, hunting for chic souvenirs and collectibles in places like Holston Mountain Artisans. 

Surrounded by the picturesque peaks of the Blue Ridge Mountains, Abingdon is also famous for its stunning natural landscapes. As such, outdoor opportunities abound, beckoning hikers, bikers, and adventurers to explore its open spaces. One of the best outback routes is the Virginia Creeper Trail, a scenic, isolated hiking and biking path from the town to Whitetop. 


Downtown Culpeper, Virginia.
Downtown Culpeper, Virginia.

Culpeper has seen a lot since its inception in 1759. From the Revolutionary War and the Gold Rush to the Civil War, this small community in Culpeper County boasts historical wealth, which you can explore at the Museum of Culpeper History. Set in a 4,000-square-foot brick building, the facility chronicles Culpeper’s past from the dinosaur era to the 20th century through various exhibits. You can get a more vivid picture of life in old Culpeper at Burgandine House, a 1700 structure that once served as headquarters for the local Historical Society. But history is not the only thing that draws visitors to Culpeper. The town boasts quaint natural spaces you can visit to be one with nature. Rockwater Park offers a laid back setting with almost 2 miles of trails, a splash pad, and other public amenities. 


Carillon Park, Luray, Virginia.
Carillon Park in Luray, Virginia.

Luray provides adventurers with the perfect playground to explore Virginia’s wild backcountry. This little location lies in the lush Shenandoah Valley and is best known for the mysterious Luray Caverns. As the largest cavern in eastern America, the site features a network of caves with dramatic rock formations, offering explorers an otherworldly experience. However, the town’s crowning jewel is the Shenandoah National Park, where outdoor enthusiasts can get lost in a natural wonderland of dense forests, secluded trails, and fantastic wildlife away from civilization. 

If you fancy up-close animal encounters, Luray Zoo houses a sanctuary for rescued creatures that could use some TLC. There are various species of birds, reptiles, and primates that you can cozy up to at the petting zoo. Meanwhile, car enthusiasts will fancy a tour of the Car & Carriage Caravan Museum, with a chance to admire classic and vintage automobiles. 


The marina at Chincoteague, Virginia.
The marina at Chincoteague, Virginia. Editorial credit: Kosoff /

Virginia’s sole resort island is one of the best places you can visit on the state’s eastern shore. With a tiny population of less than 4,000, it welcomes travelers to enjoy its stunning natural surroundings. The town is a known gateway to the Chincoteague National Wildlife Refuge, a 14,000-acre expanse and diverse ecosystem with a charming herd of wild ponies. There are numerous scenic sights to savor in Chincoteague, and the best way to do this is to climb the Assateague Lighthouse, where sweeping views of the Assateague and Chincoteague await. If you want a comprehensive tour of the island, you can hop aboard Captain’s Dan Around the Island Tours to enjoy an easygoing trip along the area's shoreline, with sightings of wild ponies, bald eagles, and dolphins. 


Aerial view of Fredericksburg, Virginia.
Aerial view of Fredericksburg, Virginia.

A Virginia itinerary cannot be complete for American historians without visiting Fredericksburg. This small community along the scenic Rappahannock River was founded in the 1720s and played a noteworthy role during the American Civil War. It houses various reminders of the conflict-riddled era, highlighted by the Fredericksburg and Spotsylvania National Military Park. This former battleground is credited with hosting the bloody climax of the Civil War. But suppose you want a broader perspective of the events during the war. In that case, Fredericksburg Battlefield Visitor Center does a wonderful job of preserving the history with interactive exhibits and guided tours. 

Besides the infinite history, Fredericksburg has other points of interest that will break the monotony. Alum Spring Park is a hidden gem that shields you from the stresses of the urban center. This serene nature space, with shaded walking paths and wooded surroundings, presents the ideal relaxation and meditation atmosphere. 


St Lukes Church and Cemetery in Smithfield Virginia
St. Lukes Church and Cemetery in Smithfield, Virginia.

Smithfield is another historic town and one of Virginia’s oldest English settlements. Situated on Isle of Wight County, the city gained fame for its agricultural contributions, particularly for producing the Smithfield ham. Today, walking through the town feels like stepping into the bygone eras. Isle of Wight County Museum shares the story of the county and surrounding region through various interactive exhibits and hosts the World’s Oldest Ham. 

You will come across the beautiful Windsor Castle Park in the Historic District. This former plantation-turned-public park sits along a cozy river with almost 4 miles of scenic woodland trails, allowing you to explore the charming surroundings. If you fancy a cultural experience, you can visit the Smithfield Farmers Market to interact with the locals and sample some fresh offerings, such as meats, wines, and craft brews. 


Aerial view of Lexington, Virginia.
Aerial view of Lexington, Virginia.

Lexington charms tourists with a picturesque townscape and rich history, which stretches back to the colonial era. The seat of Rockbridge County is the final resting place of two prominent Confederate personalities, Stonewall Jackson and General Robert E. Lee. You can glimpse Jackson’s indelible legacy at the Jackson House Museum, his abode between 1858 and 1861. The building still houses its original furnishings from the 1800s. Meanwhile, you can pay your last respects to General Robert E. Lee at the University Chapel & Galleries, which also doubles as a National Historic Landmark. 

For those who prefer outdoor pursuits, a hike along the picturesque Chessie Nature Trail is the perfect way to explore the open spaces. This secluded route stretches 7 miles, linking Lexington to Buena Vista, with wildlife viewing opportunities. 

Cape Charles

The Cape Charles Beach on the Chesapeake Bay, in Cape Charles, Northampton County, Virginia
The Cape Charles Beach on the Chesapeake Bay in Cape Charles, Virginia.

For a tiny location, Cape Charles packs a punch of touristy delights, making it one of the best small towns in Virginia to escape the city rigors. It is situated on the Chesapeake Bay and boasts spectacular beach scenery with charming water views. You can soak some of the best vistas on a scenic drive along the Chesapeake Bay Bridge-Tunnel. 

But if you do not want to get behind the wheel, you can enjoy a relaxed stroll in the Cape Charles Natural Area Preserve. The highlight of this pristine natural space is a lengthy promenade, which traverses a forested area, culminating in panoramic views of the Chesapeake Bay. Meanwhile, history buffs can visit the Cape Charles Museum to explore the local art and cultural heritage. Furthermore, you can get more hands-on experience in the Cape Charles Historic District, listed on the National Register of Historic Places.


 Downtown Historic Staunton, birthplace of President Woodrow Wilson
Downtown historic Staunton, birthplace of President Woodrow Wilson.

Staunton’s modest beginnings date back to 1747 when it was established before playing a role in the Civil War and American Revolutionary War. However, what puts this modest town on the map is that it was the birthplace of President Woodrow Wilson. You can tour the home and learn about his legacy at the Woodrow Wilson Presidential Museum & Library. For an immersive cultural experience, the Frontier Culture Museum is a must-visit for visitors in town. Spanning 200 acres, it is the largest open-air museum in the region and exhibits traditional rural structures from Africa, America, and Europe. 

You will notice Staunton’s rich heritage in the 19th-century structures hosting galleries, museums, and restaurants in its historic downtown. The R.R. Smith Center for History and Art is an excellent pastime for art connoisseurs, with a chance to browse charming galleries and take a class to improve your art technique. 


The sign of the Seven Bends State Park near Woodstock, Virginia.
The sign of the Seven Bends State Park near Woodstock, Virginia.

Not to be mistaken for New York’s famous festival destination, Woodstock, Virginia, is the seat of Shenandoah County and houses over 5,000 residents. One of the top spots to check out in town is the Woodstock Museum of Shenandoah County. The complex features two 18th-century structures and exhibits medieval artifacts, including clothing, local pottery, and photographs. Woodstock also hosts several wineries you can visit for tastings, including Muse Vineyard and Winery. 

Woodstock's outdoor scenery is irresistible, with scenic natural landscapes to explore. Seven Bends State Park is one of the best places to be one with nature. It houses charming picnic spaces and hiking trails that lead to the Shenandoah River, offering a sweet escape from the crowded urban center. 


Aerial view of Farmville, Virginia.
Aerial view of Farmville, Virginia.

Sitting about 64 miles from Richmond, Farmville is an excellent day trip to escape the hustle and bustle of the big city. This chilled-out village of about 7,500 people harbors fascinating Civil War and Civil Rights history, which will entice any history buffs visiting the town. A good example is the Robert Russa Moton Museum, the birthplace of the student-led Civil Rights struggle in America. It is also home to the High Bridge Trail State Park, which passes through downtown Farmville. The 31-mile route is perfect for hiking, biking, or horse riding and presents magnificent views of the surroundings. For more quality time outdoors, you can visit Wilck’s Lake, a cute natural area of about 150 acres. It also has a 55-acre lake and offers recreational opportunities like hiking, fishing, and picnicking.


Street in Leesburg, Virginia
Street in Leesburg, Virginia. 

With a legacy dating back to 1740, Leesburg is an ideal destination for those interested in Virginia’s history. The town is renowned for its well-preserved Historic District, listed in the National Register of Historic Places. This leaves several historical landmarks to discover, such as George C. Marshall’s Dodona Manor. But Leesburg is a developed town that balances its historical attractions with more contemporary pursuits. If you crave retail therapy, you will find generous shopping opportunities at Leesburg Premium Outlets or Village at Leesburg. Those who like to hang out in the open spaces will appreciate the atmosphere of Morven Park Grounds. This 1,000-acre estate houses many attractions, including the Winmill Carriage Museum, Morven Park Mansion, and biking and hiking trails. 


Historic neighborhood in Occoquan, Virginia.
Historic neighborhood in Occoquan, Virginia.

Occoquan is a resilient Prince William County town that has survived catastrophic fires, the Civil War, and other disasters. This tiny village of over 1,000 residents beckons travelers to experience unique Native American and Civil War history. It hosts several iconic landmarks, but the 18th-century Mill House Museum is the highlight. Despite a simple stone-made façade, the museum houses a wealth of history, with exhibits dating centuries ago.  

However, Occoquan is more impressive if you like to spend time outdoors. It has numerous spaces worth visiting, and you can start at River Mill Park. This small nature area borders the Occoquan River, providing a peaceful setting for a family day out. You will find more room at the Occoquan Regional Park, which spans 350 acres. It also means more opportunities for recreational activities, ranging from hiking and picnicking to kayaking and canoeing. 

The Takeaway

Virginia serves an overdose of America’s history, from the Revolutionary War to the Civil War and the Civil Rights Movement. But it is also surrounded by unique natural landscapes, making it perfect for outdoorsy tourists. Whether coming for the history or the outdoor adventure, you will find it all and then some in these underrated towns in Virginia.


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