Woman on beach watching wild horses of Assateague Island National Seashore.

14 Prettiest Towns In Virginia

Virginia is a state in the Mid-Atlantic that sits between the Atlantic Coast and the Appalachian Mountains. Nicknamed the Mother State for its role in being carved into states such as Kentucky, it is a treasure trove of history and natural beauty. With origins dating back as far as 1606, Virginia boasts an array of pretty small towns that offer a glimpse into the nation's past. Virginia is also geographically diverse, covering everything from mountain ranges such as the incredible Blue Ridge Mountains and rugged rocky trails, to spectacular sandy beaches and lush green forests.

Summer VibesThese Small Towns in Virginia Come Alive in Summer

Abingdon

Fall colors at the historic Martha Washington Inn in Abingdon, Virginia
Fall colors at the historic Martha Washington Inn in Abingdon, Virginia.

Abingdon stands as living proof to The Mother of State’s natural allure and rich history, boasting 20 blocks of historic sites. The Martha Washington Inn & Spa, operating since 1832, and the Barter Theater, designated the "State Theatre of Virginia," offer a glimpse into bygone eras. Introduce some adventure to your visit at Abingdon and find and challenge yourself to the beautiful outdoors the town enjoys. Must-see hiking destinations in the area include the Virginia Creeper Trail, Grayson Highlands State Park, and local vineyards.

Cape Charles 

Aerial View of Beach Homes in Cape Charles Virginia Seen from the Chesapeake Bay
Aerial view of beach homes in Cape Charles, Virginia. Seen from the Chesapeake Bay.

A large concentration of turn-of-the-century buildings can be found in Cape Charles, a bay town listed on the National Register of Historic Places. Renowned for its clear water beaches and weekend escape atmosphere of rentals and entertainment destinations, Cape Charles is a paradise for “beach bums” and watersport enthusiasts. Cape Charles is the ideal summer escape in Virginia for an overnight beach trip with a new cotton candy sunset to look forward to daily.  

Onancock 

Early evening street scene down Market street lined with red brick buildings under blanket of layered stratocumulus cloud cover
Early evening street scene down Market Street, Onancock, VA. Image credit John Blottman via Shutterstock.

Another gem on the eastern shore, Onancock, once a bustling port, has transformed into a charming, walkable waterfront city. Today, travelers relish its serene atmosphere and friendly locals. Spend the day in the water canoeing or take a ferry trip to Tangier Island. Strolling downtown will immerse you in the region's history with well-preserved historical sites like the Ker Place, Watermans Museum, and many Victorian-style buildings like Hopkins-Beechlawn House and Scott Hall. 

Lexington 

Historic downtown town city in Virginia countryside Shenandoah mountain village, sign for bistro, restaurant
Historic downtown of Lexington. Image credit Kristi Blokhin via Shutterstock.

Renowned for hosting the Virginia Military Institute and Washington and Lee University, Lexington is also known as the place of the first shot fired in the American Revolutionary War. The town is steeped in educational and military history and enjoys an upscale, classy atmosphere and diverse community thanks to its student population. The Virginia Military Institute Museum provides insight into the town's past, while horse-drawn tours enrich the experience. Nature lovers can explore Bridge State Park, where the Natural Bridge majestically stands over Cedar Creek, tucked away between the lush greenery. 

Chincoteague

Aerial view of the Long Bridge to Chincoteague Island in Virginia. Reserve with a wide variety of birds and wild horses.
Aerial view of the Long Bridge to Chincoteague Island in Virginia. 

Also located on the eastern shores is the small island of Chincoteague, the gateway to Chincoteague National Wildlife Refuge. Every summer since 1925, foals and ponies are gathered up for the world-famous annual Pony Swim traversing the Assateague Channel. Visit The Museum of Chincoteague to learn all about the history behind the wild horses. During the 1960s, the town became famous for publishing "Misty of Chincoteague," a tale of the island's favorite ponies. The area was synonymous with oyster production in earlier days, but it has now become a laid-back, relaxing fishing hotspot. Must-see landmarks to remember the town include The Assateague lighthouse on the horse-rich adjacent Island, offering the area's best views of Chincoteague from its beacon. 

Coeburn 

Bridge crossing over Little Tom's Creek to Ringley Park.
Bridge crossing over Little Tom's Creek to Ringley Park.

In the heart of Southwest Virginia, the small town of Coeburn, near Jefferson National Forest, invites nature lovers with its small population of less than 2,500. Outdoor lovers can enjoy some of the best hiking trails, such as the Guest River Gorge Trail, High Knob Lake Trail, and The Little Stony Recreation Trail. Coeburn also enjoys a decent range of family fun destinations like Lonesome Pine Motorsports Park and Spearhead Indoor Adventure Complex where you can test your axe throwing skills. 

Lynchburg

Lynchburg, Virginia, USA downtown city skyline at dusk.
Lynchburg, Virginia, USA downtown city skyline at dusk.

Another town in Virginia with a rich history, with more than one site registered on the National Register of Historic Districts. Point of Honor, the Old Court House and Lynchburg Museum, Patrick Henry's Red Hill, the National D-Day Memorial, and the Appomattox Court House National Historical Park are the perfect stops for history fanatics. Lynchburg sits on the James River with a Stunning Blue Ridge Mountains backdrop, a hotspot for endless outdoor fun, such as hiking, biking, and camping. 

Farmville

Entrance of the High Bridge Trail from the Main Street downtown.
Entrance of the High Bridge Trail from the Main Street downtown. Image credit Lekali Studio via Shutterstock.

Situated in both the Prince Edward and Cumberland Counties, a stone's throw from Richmond, lies Farmville's small yet compelling enclave. Hosting the esteemed Longwood University and The 125-foot High Bridge, an Instagramable landmark during sunsets. Visitors can also enjoy fishing or kayaking at one of the rivers surrounding the town, such as Sandy River. A walk downtown is complete with an old town vibe featuring many museums, such as the Moton Museum and Transportation Heritage Museum, to check out!

Luray

Cave stalactites, stalagmites, and other formations at Luray Caverns, Virginia.
Cave stalactites, stalagmites, and other formations at Luray Caverns, Virginia.

Luray is first on every bucket list for the perfect cabin getaway, for it is a natural paradise with a mix of woodlands, trails, forests, and wildlife. The small city is famous for its proximity to Shenandoah National Park as well as the George Washington National Forest, featuring many outdoor leisure activities and multiple hiking trails leading to stunning vistas. Luray is also known as Luray Caverns, full of mirrored pools, stalactites, columns, and stalagmites, perfect for the adventurers in the group!

Middleburg

Indian 111 Classic Motorbike parked outside The Red Fox Inn and Tavern in Middleburg, Virginia
The Red Fox Inn and Tavern in Middleburg, Virginia. Image credit Nigel Jarvis via Shutterstock.

Middleburg's storied legacy traces its lineage to the 1700s when its title was "America's Horse and Hunt Capital" for its famous fox hunting community and steeplechase horse races. In addition to its abundant wildlife and vibrant nature, it is Middleburg’s historic shopping destination. It is only a mile long, filled with equestrian shops, high-end clothing boutiques, fine art galleries, and so much more. Shop antiques at The Shaggy Ram, or hunt for some classy attire and support small local businesses. English Country Classic’s fashion shop, the community thrift shop, and Highcliffe Clothiers are the perfect shops to start with!

Floyd 

A view of an old barn in the foothills of the Blue Ridge Mountains in Floyd County, Virginia
A view of an old barn in the foothills of the Blue Ridge Mountains in Floyd County, Virginia.

This lovely mountain town is known for its hospitality and vibrant music culture, hosting the annual FloydFest, a five-day music and art festival set against the backdrop of Southwest Virginia's scenic landscape. The town in Floyd County enjoys a lively artistic scene and a range of creative family-owned businesses. Cool places to check out while in town include A Little Monkey Business for funky clothing and collectibles, Art by Linda Rae Russo, and Bell Gallery for Winning Landscape Photography, all perfect for souvenir-finding to commemorate the trip.

Occoquan 

New housing in historic Occoquan.
New housing in historic Occoquan. Image credit Malachi Jacobs via Shutterstock.

Sitting on the banks of the Occoquan River in Prince William County, it is home to America's first automated grist mill. Plan a trip to Occoquan Bay National Wildlife Refuge and River Mill Park while experiencing and engaging in the historical and artsy community. Mill Street is where all the town’s magic happens, as visitors can find everything from museums such as the Mill House Museum, to small independent galleries such as Local Color and the Loft Gallery. 

Smithfield

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

Distinguished as the "Ham Capital of the World," Smithfield unveils its storied legacy with various architectural gems, embracing Colonial to Victorian motifs. The charming Main Street emerges as a veritable treasure trove of shops, each beckoning with timeless allure. As history harmoniously clashes with culinary delights, visitors explore historic architecture and locally acclaimed businesses like The Wight Courthouse, Summerwind Vineyard, and the venerable St. Luke Historic Church and Museum. 

Staunton

Downtown Historic Staunton, birthplace of President Woodrow Wilson
Downtown historic Staunton, birthplace of President Woodrow Wilson. Image credit MargJohnsonVA via Shutterstock.

Cradled by the Shenandoah Valley's majestic mountains, Staunton is a nexus of historical grandeur and vibrant culture. Home to the American Shakespeare Center and The Frontier Culture Museum, Staunton echoes and embraces its cultural cadence. A harmonious accord of history and nature is orchestrated at Gypsy Hill Park, where verdant expanses invite visitors to leisurely meander. However, food connoisseurs can skip all history and explore incredible and renowned culinary staples such as Clocktower Eats and Sweets, Gonzos Pollo, and Gloria Pupuseria. 

Read MoreThe 7 Most Underrated Towns in Virginia

Conclusion

From Lynchburg's historical charm to the tranquil cabins of Luray, Virginia's small towns offer an authentic journey into its heart and soul. These hidden gems of Southern charm and hospitality provide a perfect romantic getaway, day trip, or lengthier vacation. Whether captivated by history, natural beauty, or vibrant culture, Virginia's small towns invite all to experience the state in all its diverse glory!

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Moe Ergig August 27 2023 in Places

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