The 12 Best Small Towns in Virginia to Add to Your Travel List

Virginia is known for its many urban areas with intricate history and notable architecture, such as Richmond and Alexandria. But for all of the metropolitan places showcasing highlights of The Old Dominion, there are less-populated areas that rival big city to-do lists. Although these regions may not be as well known as their more urban counterparts, visiting one of Virginia's smaller towns can give you an authentic taste of what this Southern state has to offer.

Aerial view during golden hour in autumn of Farmville, Virginia
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From communities filled with music and culture to places that focus on the beautiful landscape and history, these areas showcase the diversity that is found within the state of Virginia. So, whether you're already planning to travel the East Coast or are looking for your next relaxing getaway, here are 12 of the best small towns in Virginia to put on your itinerary.

A view of the Blue Ridge mountains overlooking a mountain top cabin
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Tucked into the foothills of the Blue Ridge Mountains in Southwest Virginia lies the picturesque area of Bedford. Visitors can enjoy the tranquility of the outdoors at its many surrounding orchards, yet the downtown area houses multiple antique shops and art galleries. History lovers will enjoy visiting the National D-Day Memorial, and nearby Smith Mountain Lake offers watersports and rentals for an adventurous vacation.


With its proximity to the Blue Ridge Parkway coupled with the fact that the James River runs through it, it's no wonder that Buchanan is picturesque. The small urban center features various locally-owned eateries and shops, and the town hosts multiple festivals throughout the year. Highlights for outdoor enthusiasts include the Upper James River Water Trail and crossing the Buchanan Swinging Bridge, dating back to 1851.

Ponies grazing Chincoteague National Wildlife Reserve, Chincoteague Island, Virginia
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One of the unique aspects of Chincoteague is the annual Pony Swim, where visitors can witness over 100 foals and adult ponies traverse the Assateague Channel. Not only are the horses a draw, but Chincoteague Island offers a glorious taste of Virginia's beautiful coastline. A fabulous beach with a quaint, waterside town allows folks to experience a bit of R&R before heading back home.


Civil War history is present throughout the state of Virginia, and Culpeper's Cedar Mountain Battlefield — where American Red Cross Founder Clara Barton once attended to soldiers — attracts many historians. Like many other northern Virginia towns, Culpeper has a plethora of locally owned eateries and shops, although the outskirts feature many wineries that produce varietals from Virginia-grown fruit.

Aerial view during golden hour in autumn of Farmville, Virginia
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As a thriving college town, Farmville has a bustling hub featuring boutiques, restaurants, and a brewery. The area is also known for its exceptional outdoor scene with opportunities for visitors to fish, hike, and kayak. One highlight is the High Bridge Trail, which is 31 miles of pathway filled with folks walking and biking (hint: rent bikes downtown). The Moton Museum is a former high school where students protested inequality and furthered the Civil Rights Revolution.


Step back into history and experience small-town living by taking a Historic District Walking Tour in Fincastle, where the courthouse securely keeps documents signed by Thomas Jefferson. On a small scale, Fincastle rivals Williamsburg with its historic buildings, such as an old jail and blacksmith shop. However, the town also has art galleries, wineries, and a pie shop for those with non-historical interests.

Older folks gather outside the Floyd Country Store
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The mountain town of Floyd serves as a haven for music and features the annual Floyd Fest, a 5-day music and art festival set against the backdrop of Southwest Virginia's scenic landscape. The area is filled with fascinating moonshine history and artisans who offer glimpses into their process via studio tours. In addition, music lovers will enjoy visiting the Floyd Country Store, which hosts live events several times a week.


Perhaps one of the most unique areas within the state of Virginia is the town of Luray, which houses Luray Caverns, the largest caverns on the East Coast. When not underground in the caves, folks can explore a landscape that offers mountain activities and watersports, which is no wonder, as Shenandoah National Park and the river are close. Also nearby are battlefields, museums, and plenty of wineries.

Rolling green hills of a farm and the countryside, Goodstone Inn in Middleburg, Virginia.
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The town of Middleburg has long been a favorite among the political elite — think Jackie Kennedy — due to its proximity to Washington D.C. Serving as the middle point between Winchester and Alexandria (hence the name Middleburg), it was established in the late 1700s and has a longstanding horse and hunt history. In addition, it is peppered with wineries, specialty shops, upscale eateries, and charming places to stay.


Most of downtown Orange was influenced by the railroad, which still passes through the center of town. Visitors can take a historic walking tour, highlighting several former rail buildings, or simply enjoy strolling through the downtown visiting shops and eating establishments. The fourth president's former home, James Madison's Montpelier, is on the outskirts and is open to touring and periodically hosts hunting races.

The sun sets in Tangier, Virginia, May 15, 2017, where climate change and rising sea levels threaten the inhabitants of the slowly sinking island.
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Tangier Island

Located in the Chesapeake Bay area of Virginia, Tangier Island focuses more on harvesting Virginia oysters than it does a fast-paced, modern lifestyle. If it sounds quaint, it is. Tangier Island is a fabulous place to go if you crave a laid-back lifestyle and delectable, freshly caught seafood.


Wytheville's eclectic assortment of attractions will appeal to a variety of tastes. The area has a deep history and houses several attractions on the U.S. National Register of Historic Places. Visitors can watch dirt track car racing, peruse the local farmers market, or eat a meal while viewing a Broadway-style show at Wohlfahrt Haus Dinner Theatre. Motorcycle enthusiasts should make time to experience Southwest Virginia's The Claw of the Dragon driving trail.

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