9 Quirky Little Towns In Virginia
Virginia is filled with friendly, small communities, but a handful stand out for their playful personalities and unexpected character. Towns like Smithfield and Winchester lean into their quirks through creative local traditions, offbeat attractions, and a welcoming spirit with unique festivals and unexpected delights. From the Birthplace of Country Music and the Apple Capital of the World to wild ponies and famous smoked ham, these destinations invite travelers to slow down, explore, and enjoy the delightful surprises woven into everyday life.
Bristol
Just a stone's throw from its sister city in Tennessee, Bristol is a distinct small town where music, art, and the outdoors combine for a unique adventure. Known as the “Birthplace of Country Music,” Bristol’s legacy has expanded far beyond the small town’s borders. Any trip to Bristol requires a stop at the Birthplace of Country Music Museum, which explains more about the genre’s origins and the 1927 Bristol Sessions that launched country music. While heading to the museum, stop by the Country Music Mural downtown, which celebrates the town’s musical legacy. For a bit of a quirky detour, head to State Street, where Tennessee and Virginia’s border meets, and you can walk and shop along the actual state line.
Nearby, history lovers can step inside the William King Museum of Art, a former school transformed into a cultural hub showcasing Appalachian art and craft, with rotating exhibitions. Downtown Bristol, Virginia, adds even more character with its locally owned shops, such as Aroma Coffee House, serving organic coffee from Honduras and other Latin American countries. For a relaxed outdoor experience, the Sugar Hollow Park area offers green space and trail access along Beaver Creek, as well as a pool, campground, and picnic facilities.
Smithfield
Located in Isle of Wight County, Smithfield is famed for curing and producing Smithfield ham, and the town's legacy is evident throughout, with several sites serving as reminders. Throughout your visit, check out the Porcine Parade, a series of pig sculptures scattered throughout downtown that make for a fun scavenger hunt activity for the whole family. Afterward, head to Darden's Country Store, a long-standing community staple offering traditional hams, smoked meats, and other local favorites. Here, you can try some of Smithfield's iconic hams firsthand.
Once you've had your fill, visit St. Luke's Historic Church & Museum. Considered America's oldest brick church, St. Luke's offers guests a trip back in time and a history lesson along the way. The museum also hosts academic lectures, living history events, and guided tours of both the church and graveyard. For another uniquely historic experience, the 1750 Isle of Wight Courthouse is one of the few remaining colonial government centers and a great one-of-a-kind destination for history enthusiasts.
Floyd
The main attraction in this charming small town is the Floyd Country Store. By day, the shop sells everything from candy and ice cream to gifts and apparel. a local hangout with square dancing, food, and plenty of music. Come the weekend, however, it transforms from a country store to a local hot spot for live music, thanks in large part to its Friday Night Jamboree, a beloved bluegrass tradition that draws musicians and dancers from across the region. Summer visitors can also attend Floydfest, a five-day music and arts festival held in the Blue Ridge Mountains. Not just for music, this festival brings together all of the creative spirits in Floyd for an exciting summer week.
Those looking to immerse themselves in the vast natural landscape can journey to the Buffalo Mountain Natural Area Preserve. Here, adventure seekers can hike to incredible panoramic views and zipline through the mountains. The Lee Farm in nearby Dugspur also offers a quaint cottage, a glamping tent, or caravan replicas for a memorable camping experience.
Staunton
With a vibrant cultural scene, there isn't necessarily one thing that stands out as unique, but an entire town filled with one-of-a-kind experiences and opportunities. Arts lovers can visit the American Shakespeare Center's Blackfriars Playhouse, a historically accurate replica of the original indoor Elizabethan theatre that staged Shakespeare's iconic plays. Immerse yourself further in the arts with a visit to the Camera Heritage Museum, where visitors can tour antique camera exhibits and learn more about the history of photography. Finish your cultural trip with a tour of the Frontier Culture Museum, the largest open-air living history museum in the Shenandoah Valley, featuring original and replica buildings from early American immigrants.
After a journey through the town's most culturally significant attractions, stroll through town and stop by some of the more unique community locales. Sunspots Studios Glassblowing offers guests glassblowing demonstrations and the opportunity to purchase these unique pieces of art. Finish your trip at Redbeard Brewing Company for a sample of the local craft brews before heading out of town.
Damascus
Better known as "Trail Town USA," Damascus is an outdoor haven with seven trails that run through town. One of the seven trails, the Virginia Creeper Trail, is a popular section that offers scenic views, historic paths, and a biking route. The famed Appalachian Trail also provides the same outdoor adventure, though it passes directly through the downtown area. This one-of-a-kind geographical feature comes alive during Appalachian Trail Days, an annual festival where tens of thousands of hikers descend on Damascus for parades, live music, gear repair stations, and playful outdoor competitions. Damascus is a hiker's hub with numerous paths to explore the beautiful outdoor landscape.
Beyond its numerous trails, the town offers a wide range of activities, even if you don't plan to hike. The Damascus Old Mill Inn not only offers comfortable accommodations but also provides guests with a picturesque waterfall view on the premises. Nearby, the Barter Theatre presents an evening of entertainment, making it the nation's longest-running professional theater. Also in town is Damascus Brewery, a local spot that offers a wide variety of beers and opportunities to mingle with the community.
Chincoteague
Just off Virginia’s Eastern Shore, Chincoteague is a quirky coastal town where untamed beauty, small-town charm, and a touch of whimsy come together. Best known for the Chincoteague ponies that roam nearby Assateague Island, the town has a gentle, dreamlike atmosphere that feels different from typical beach destinations. A visit isn’t complete without stopping at the Museum of Chincoteague Island, which shares stories about the region's heritage and the famous wild ponies.
Of course, you must see these beautiful beasts for yourself at the Chincoteague National Wildlife Refuge, where scenic trails lead to marshes, forests, and ocean views teeming with wildlife. Another favorite is the Assateague Lighthouse, a striking red-and-white tower that provides a rewarding climb and a sweeping coastal panorama. To round out the experience, take a sunset boat tour where you might spot dolphins alongside the iconic ponies grazing in the distance. Back in town, check out Robert Reed Waterfront Park for views of the harbor and a peaceful place to unwind, and take a stroll along Maddox Boulevard and browse the colorful local shops that give the town its character, like The Brant, which offers a unique Build-A-Pony experience.
Wytheville
Tucked in Southwest Virginia, Wytheville is a small town that delights visitors with its bold personality and playful quirks. Its most eye-catching landmark is Skeeter’s, a local institution known for its world-famous hot dogs, which are unmissable when visiting Wytheville. To truly appreciate what makes Wytheville unique, however, one must look to the skies. The Wytheville Lookout Tower offers expansive views of the valley and stands 100 feet tall. Wytheville is also known for its devotion to its love of hot air balloons, with a colorful water tower decorating the town, and for hosting the Chautauqua Festival, an eight-day free arts and music extravaganza that kicks off with a stunning hot air balloon glow.
Beyond balloons, a visit to the Edith Bolling Wilson Birthplace Museum offers insight into the life of the First Lady, often referred to as "the first woman President" for her leadership and integral role alongside her husband, Woodrow Wilson, during World War I. While exploring Main Street, keep your eyes peeled for murals, art installations, and unique sights, such as The Big Pencil, for a colorful snapshot of local pride and the eclectic charm that defines the community. After wandering downtown, head to Crystal Springs Recreation Area for peaceful hiking trails surrounded by mountain scenery. Outdoor lovers also enjoy the nearby Big Survey Wildlife Management Area, where quiet forests and overlooks make it ideal for a slow afternoon escape.
Luray
Luray stands out as one of Virginia’s most whimsical small towns thanks to its deep connection to the underground world beneath it. The town is best known for Luray Caverns, the largest caverns in the eastern United States and home to the Great Stalacpipe Organ, a one-of-a-kind instrument that uses the cave’s stalactites to create music. This unusual attraction and intricate geographic landmark alone give Luray a delightfully eccentric reputation. Above ground, the town leans into its offbeat charm with retro stops like the Luray Valley Museum, which houses an eclectic collection of antique cars, farm equipment, and roadside Americana.
A must-visit for history lovers is the Belle Brown Northcott Memorial, also known as the Luray Carillon Singing Tower, a monument to Colonel T.C. Northcott's wife that features a 47-bell carillon and stands 117 feet tall. Nature also plays a starring role here, with Shenandoah National Park just minutes away, offering scenic drives, waterfalls, and hiking trails that contrast beautifully with the town’s underground wonders.
Winchester
Winchester blends rich history with unexpected eccentricities, giving it a quirky edge that surprises first-time visitors. The town proudly claims to be the “Apple Capital of the World,” a title celebrated each fall during the Shenandoah Apple Blossom Festival, a lively event filled with parades, marching bands, and apple-themed treats. History runs deep in Winchester, particularly at the Patsy Cline Historic House. In this seasonal attraction, fans of the legendary singer can tour her childhood home and learn about her rise to fame. For something more offbeat, the Museum of the Shenandoah Valley pairs refined art galleries with rotating exhibitions and beautifully landscaped gardens, including the historic Glen Burnie House.
Old Town Winchester adds a commercial and cultural twist, with pedestrian-friendly streets lined with indie shops, cafes, and historic architecture that feels both lived-in and lively, including Antica Trattoria, a cozy Italian eatery serving homemade pasta. Nature lovers can escape to Jim Barnett Park, which offers walking trails, pools, disc golf, and plenty of green space in the heart of town.
Not Your Average Virginian Towns
Exploring Virginia’s quirkiest towns offers a refreshing look at small communities that embrace individuality instead of blending into the background. These places celebrate creativity, heritage, and local pride in ways that feel sincere and distinctly their own. Visitors will find colorful events, unexpected landmarks, and a sense of personality that goes beyond typical tourist stops. Whether you wander through artsy districts, discover unusual museums, or enjoy conversations with residents who love sharing their stories, each town reveals something memorable. Together, they show how unique experiences can thrive in often-overlooked places, making them well worth the journey.
