Virginia serves up a rich tableau of small-town life to explore, from charming communities nestled in the Shenandoah Valley to the laidback beachside communities on the Eastern Shore. Many of Virginia’s towns have thriving arts and culture scenes where you’ll find art galleries, local festivals, bluegrass and country music shows, and even Shakespearean theatre. Towns like Lexington and Onancock are great for exploring Virginia’s history, thanks to their restored heritage buildings and museums.

    Whether you’re hoping to delve into local culture and history or seeking a peaceful retreat close to nature, these small towns are worth checking out during a road trip to Virginia. 

    1

    Bristol

    A rich history of country music to discover

    Bristol is a small town with a big place in American country music folklore. Located on the Virginia-Tennessee state border, it's where some of the earliest recordings of country music take place.

    Stop by the Birthplace of Country Music Museum to learn more about the 1927 Bristol Sessions and other historic moments in the town's musical heritage. Delve deeper into its local culture and history at the Bristol Train Station and the Paramount Center for the Arts. Each September, the town hosts the Bristol Rhythm and Roots Reunion festival, where crowds turn up for a toe-tapping good time.

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    photo by Aplomado~commonswiki (CC BY-SA 3.0) modified

    2

    Damascus

    A hotspot for hikers and bikers

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    Damascus offers an ideal base for outdoor lovers and hikers in Virginia. Surrounded by the Blue Ridge Mountains, the town is also known as Trail Town USA for its location at the intersection of 7 trails, including the Appalachian Trail and Virginia Creeper Trail.

    Pedal-powered visitors can find plenty to explore, with the Trans-America National Bicycle Trail among the bike paths in the area. Those looking for a lazier escape could book into one of the town’s quaint bed and breakfasts and just relax while taking in the serene mountain views.

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    3

    Onancock

    A Sleepy seaside town and historic site

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    Onancock is a small town in the quiet Eastern Shore of Virginia that has a ‘land that time forgot’ feel. Fringed by the Atlantic Ocean and the Chesapeake Bay, it's the kind of place where you could let the hours and days slip away with ease while relaxing on the wide veranda of a Victorian mansion-turned-inn. 

    The town’s charming streets are lined with boutique shops, cafes and art galleries that might coax you out for a bit of exploring. With little traffic, it’s easy to get around by foot. You could head down to the wharf to enjoy some waterfront dining, or hire kayaks and go for a paddle along Onancock Creek.  

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    photo by Ser Amantio di Nicolao (CC BY-SA 4.0) modified

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    Lexington

    Go for a carriage ride through the historic streets

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    Wandering around the small town of Lexington is to step into America’s rich and complex history. The Washington and Lee University and Virginia Military Institute, lend a youthful vibrancy to the town, while its museums and historic buildings offer a peek into past days of revolution and civil war that shaped the nation. 

    For such a small town, Lexington has a surprisingly great choice of restaurants and cafes, as well as a variety of shops, antique stores and art galleries. Its location in the scenic Shenandoah Valley offers plenty of outdoor activities, including hiking, kayaking, white-water rafting, birdwatching and horseback riding. A popular hike is the 7-mile Chessie Nature Trail, which leads down an old railroad line along the Maury River.

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    photo by Zeete (CC BY-SA 4.0) modified

    5

    Staunton

    A unique combination of Shakespearean theatre and Southern charm

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    The small city of Staunton has evolved from its early days as a settler trading centre in the 18th century to a hub of arts and culture. Explore its historic streets then learn more about Virginia’s history and rural life at the Frontier Culture Museum. Or catch a play in an Elizabethan-era setting at the Blackfriars Playhouse, which was built in 2001 by the American Shakespeare Center as a recreation of Shakespeare’s indoor playhouse.

    Staunton is also the only place in Virginia to have a presidential library, as it was the birthplace of the 28th US president Woodrow Wilson. Photography buffs will want to stop by the Camera Heritage Museum, which has a remarkable collection of antique cameras dating back to the 19th century.

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    6

    Abingdon

    Historic sites and hiking trails

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    The town of Abingdon is nearly as old as the USA, having been established in 1778 – 2 years after the country won its independence. Many remnants of Abingdon’s early days still remain, and its downtown streets are lined with shops, cafes and restaurants in restored heritage buildings. Notable sites to explore in Abingdon’s historic district include the Sinking Spring Cemetery, General Francis Preston House, Martha Washington Inn and Barter Theatre.

    The surrounding Blue Ridge Highlands beckon hikers, cyclists and horseback riders, with the starting point for the Virginia Creeper Trail found at the edge of town. The 35-mile trail takes you through lush forests, rolling farmland, and over trestles towards the town of Damascus.

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    7

    Woodstock

    Gateway to outdoor adventures

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    Woodstock is a lively little town in the Shenandoah Valley that offers historic sites and great local eats to discover, as well as easy access to some of Virginia’s most spectacular mountain trails and parks. Head downtown to see such stately heritage landmarks as the Shenandoah County Historic Courthouse, a late 18th-century Greek revival building with a visitor centre and museum.

    Outdoor explorers could make their way to Wolf Gap recreation area to hike to the top of the Big Schloss rock formation, or tackle the 2-mile trek up to Woodstock Tower for fresh mountain air and panoramic views. Nearby, Seven Bends State Park has 1,000 acres of protected forest and river to explore, with hiking and biking trails throughout. Local bars like the Woodstock Brewhouse are great spots to enjoy some refreshing craft beer or local Virginia wines after a day on the trails.

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    photo by Famartin (CC BY-SA 4.0) modified

    8

    Chincoteague

    Wild ponies and idyllic beaches

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    The town of Chincoteague is a welcoming place for families in search of a seaside escape. It's on an island of the same name in the Eastern Shore of Virginia. Here, you can find pristine beaches stretching for miles and a walkable town. Join a walking and biking tour to learn more about the island’s rich history and heritage sites like Old Town Jail and the Squealer Dan Whealton House, the former residence of a sea captain known for his high-pitched voice.

    The neighbouring Assateague Island is a protected wildlife refuge where wild ponies roam free. It’s a popular destination for bird-watchers and such activities as boating, kayaking, fishing and hiking – not to mention gorging on the local oysters.  

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    9

    Floyd

    Part of the Virginia Crooked Road Music Trail

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    Floyd is a tiny town with fewer than 500 residents, but it has some big enticements for visitors with its bluegrass music scene and the incredibly scenic Blue Ridge Plateau. Floyd Country Store forms the heart of the town not only for its array of goods for sale but as a host to regular jam sessions and Appalachian music performances. Enjoy more local music at the Floyd Center for the Arts, which puts on exhibits and shows year-round, and the Blue Ridge Music Center with its “mid-day mountain music” performances from noon to 4 pm.

    In addition to the hiking trails and scenic viewpoints to explore along the Blue Ridge Parkway, you could also go for some wine tasting at such places as the Chateau Morrisette Winery or Villa Appalachia Winery.

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    10

    Luray

    Known as the “cabin capital of Virginia”

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    Luray is a serene escape from a hectic world but it's just 90 miles from Washington DC. Found near the majestic Shenandoah National Park and George Washington National Forest, the town offers a good base for discovering nearby natural wonders such as the Luray Caverns and Shenandoah River. Hikers have plenty of ground to cover, with more than 500 miles of trails crisscrossing the National Forest.

    If you’re looking to stock up on some boozy provisions for your cabin, you can check out the local tastes on a tour of the Luray's distilleries, wineries and breweries along the Blue Ridge Whiskey Wine Loop. Pick up a map of the loop at the Luray Visitor Center on Campbell Street.

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    Lana Willocks | Contributing Writer

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