13 Most Underrated Towns In Virginia To Take A Trip To

Virginia’s small towns carry big stories in surprisingly concentrated pockets. Abingdon’s walkable historic district sits at the gateway to the Virginia Creeper Trail, a former rail corridor turned beloved biking route that climbs deep into the state’s highlands. Farther east, Chincoteague connects visitors to a protected coastal ecosystem where wild ponies roam the marshes and migrating birds funnel through the Atlantic Flyway each year.

The towns ahead reveal Virginia at human scale, where a single afternoon can include art, archaeology, and a shoreline sunset!

Abingdon

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 roughly 20-block stretch of historic structures is a unique experience that allows you to explore notable venues like the William King Museum of Art and the Fields-Penn 1860 House 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.

Set amid the rolling hills of Virginia’s Appalachian Highlands, Abingdon is also famous for its scenic natural surroundings. As such, outdoor opportunities abound, beckoning hikers, bikers, and adventurers to explore its open spaces. One of the best routes is the Virginia Creeper Trail, a scenic hiking and biking path that runs from Abingdon to Whitetop Station.

Culpeper

Culpeper has seen a lot since its inception in 1759. From the Revolutionary War and a regional 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 brick building downtown, the facility chronicles Culpeper’s past from prehistoric times to the 20th century through various exhibits. You can get a more vivid picture of life in old Culpeper at Burgandine House, an 18th-century structure that once served as headquarters for the local Historical Society. But history is not the only thing that draws visitors to Culpeper. Rockwater Park offers a laid-back setting with nearly 2 miles of trails, a splash pad, and other public amenities.

Luray

Luray provides adventurers with the perfect playground to explore Virginia’s backcountry. This small town lies in the lush Shenandoah Valley and is best known for the mysterious Luray Caverns. Often described as the largest cavern system in eastern North America open to the public, the site features dramatic rock formations and an otherworldly underground landscape. Nearby, Shenandoah National Park offers outdoor enthusiasts a natural wonderland of forested trails, wildlife viewing, and scenic overlooks away from civilization.

If you fancy up-close animal encounters, Luray Zoo houses a sanctuary for rescued creatures. Visitors can see a variety of birds, reptiles, and mammals. Meanwhile, car enthusiasts will enjoy the Car & Carriage Caravan Museum, which showcases classic and vintage automobiles.

Chincoteague

One of Virginia’s most famous island towns, Chincoteague is a standout destination 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 roughly 14,000-acre expanse and diverse ecosystem with a charming herd of wild ponies. There are numerous scenic sights to savor in Chincoteague, and one of the best ways to do this is to climb the Assateague Lighthouse, where sweeping views of 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.

Fredericksburg

A Virginia itinerary for American history enthusiasts would be incomplete 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, which preserves several major battlefields from the war. For a broader perspective of the events during the war, the 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.

Smithfield

Smithfield is another historic town and one of Virginia’s oldest incorporated communities. Located in Isle of Wight County, the town gained fame for its agricultural contributions, particularly for producing Smithfield ham. Today, walking through the town feels like stepping into bygone eras. The 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 near the Historic District. This former plantation-turned-public park sits along a branch of the Pagan River with several 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.

Lexington

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 Lee Chapel at Washington and Lee University, a National Historic Landmark that also serves as a campus museum.

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 and running alongside the Maury River, with wildlife viewing opportunities.

Cape Charles

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 across the Chesapeake Bay Bridge-Tunnel or simply relax along the town beach.

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 network of trails and boardwalks that traverse a forested area and maritime dunes, culminating in panoramic views of the Chesapeake Bay. Meanwhile, history buffs can visit the Cape Charles Museum to explore the local cultural heritage. Furthermore, you can get more hands-on experience in the Cape Charles Historic District, listed on the National Register of Historic Places.

Staunton

Staunton’s modest beginnings date back to 1747, and it later played a role in both the Civil War and the broader Revolutionary War era. However, what puts this modest town on the map is that it was the birthplace of President Woodrow Wilson. You can tour his childhood home and learn about his legacy at the Woodrow Wilson Presidential Library and Museum. For an immersive cultural experience, the Frontier Culture Museum is a must-visit for visitors in town. Spanning 200 acres, it is one of the largest open-air museums 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.

Woodstock

Woodstock, Virginia, should not be confused with New York’s famous festival site. It is the administrative center of Shenandoah County and has a population of over 5,000 residents. A key attraction is the Woodstock Museum of Shenandoah County, which features two 18th-century buildings and displays historic artifacts such as clothing, local pottery, and photographs. The town also offers several wineries, like Muse Vineyard and Winery, for tasting visits.

The outdoor scenery in Woodstock is captivating, with beautiful natural landscapes to enjoy. Seven Bends State Park is an ideal spot to connect with nature, offering lovely picnic areas and hiking trails that lead to the Shenandoah River, providing a peaceful retreat from busy city life.

Farmville

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 town of roughly 8,000 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, a National Historic Landmark and the birthplace of a pivotal student-led Civil Rights protest. 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 small natural area with a lake and surrounding trails that offers recreational opportunities like hiking, fishing, and picnicking.

Leesburg

Founded in the mid-18th century, Leesburg represents an exemplary destination for individuals with an interest in Virginia’s historical heritage. The locality is distinguished by its meticulously preserved Historic District, which is inscribed on the National Register of Historic Places. Numerous historical landmarks await exploration, including George C. Marshall’s Dodona Manor. Nonetheless, Leesburg is a developed municipality that harmoniously integrates its historical sites with contemporary amenities. For those seeking retail experiences, ample shopping opportunities are available at Leesburg Premium Outlets or the Village at Leesburg. Enthusiasts of outdoor activities will particularly value the ambiance of Morven Park, a 1,000-acre estate that features numerous attractions such as the Winmill Carriage Museum, Morven Park Mansion, as well as biking and hiking trails.

Occoquan

Occoquan is a resilient town in Prince William County that has endured devastating fires, the Civil War, and other calamities. With over 1,000 residents, this small village invites visitors to explore its unique Native American and Civil War history. It features several notable landmarks, with the 18th-century Mill House Museum standing out. Despite its modest stone façade, the museum offers a rich collection of exhibits that span centuries.

For outdoor enthusiasts, Occoquan is especially appealing. It boasts numerous scenic spots, beginning with River Mill Park, a tranquil nature area along the Occoquan River, ideal for family outings. Larger and more versatile is Occoquan Regional Park, covering hundreds of acres, offering opportunities for hiking, picnicking, 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.