12 Quirky Virginia Towns You Need to Visit

Virginia is home to more than just historic landmarks and scenic landscapes—it’s also a treasure trove of quirky small towns. From charming main streets to offbeat attractions, these destinations are great for travelers seeking something out of the ordinary.

Abingdon

Nestled in the heart of the Appalachian Mountains, Abingdon is a town that blends history with the arts. Its quirky charm comes from its Barter Theatre, the nation’s longest-running professional theater, where patrons once paid for tickets with produce, livestock, and other goods during the Great Depression, allowing the theater to remain in operation. The Martha Washington Inn adds to the town’s character with its ghost stories and Civil War history.

Abingdon is also known for the Virginia Creeper Trail, a 34-mile pathway that turns an old rail line into a haven for outdoor enthusiasts. Its blend of natural beauty and historical quirkiness makes Abingdon a standout destination.

Floyd

Floyd is the place to be if you love live music and a laid-back vibe. Its quirkiness shines every Friday night at The Floyd Country Store’s Friday Night Jamboree, where locals and visitors gather for impromptu bluegrass jams. It’s a town where musicians might just pop up and start playing on the sidewalk.

In addition to its musical heartbeat, Floyd’s eccentricity is on display in its galleries and studios, filled with funky and colorful art. The Chateau Morrisette Winery adds to the mix, offering not only wine but also events like dog-friendly festivals.

Staunton

Staunton’s quirkiness lies in its theatrical and historical roots. Home to the American Shakespeare Center, it’s the only town with a replica of Shakespeare’s Blackfriars Playhouse. This makes Staunton a hub for quirky, immersive performances.

The town’s downtown area brims with Victorian architecture and eclectic shops, where you might find anything from vintage books to unique antiques. Even its food scene is a bit unconventional, with gourmet takes on Southern classics.

Chincoteague

Chincoteague is quirky thanks to its wild pony population, which roams freely on nearby Assateague Island. The annual Pony Swim, where ponies swim across a channel to be auctioned off, is an event unlike any other.

Beyond the ponies, Chincoteague boasts a serene, old-fashioned charm with its locally owned ice cream parlors, quirky souvenir shops, and the iconic Misty of Chincoteague legacy, immortalized in children’s books.

Smithfield

Smithfield is quirky in its devotion to ham. Known as the “Ham Capital of the World,” it even celebrates its meaty fame with a Ham Cam, a live feed of a famous ham at the Isle of Wight County Museum. Where else can you say you’ve watched a ham in real time?

The town’s quirky blend of history and food is reflected in its charming streets, dotted with art galleries and riverside dining. The historic Smithfield Inn adds to the character with its old-world Southern hospitality.

Lexington

Lexington’s quirkiness is rooted in its deep ties to both history and education. The town is home to two historic colleges: Washington and Lee University and Virginia Military Institute. It’s not every day you find a town with cannons and statues scattered throughout campus grounds.

Quirky attractions like the Stonewall Jackson Cemetery, where Confederate general Stonewall Jackson rests, add a unique twist to this otherwise picturesque town. Nearby Natural Bridge, once owned by Thomas Jefferson, enhances its eccentric appeal.

Onancock

Onancock’s quirkiness lies in its blend of nautical charm and artistic flair. Its picturesque harbor is a hub for boating, but it’s the ferry rides to Tangier Island that stand out. Tangier feels like stepping into a different world with its unique accent and way of life.

The Roseland Theatre, a vintage movie house, adds to the quirky vibe, while local galleries showcase an eclectic mix of art inspired by the Chesapeake Bay.

Crozet

Crozet is quirky because it feels like a wine country destination hidden in the Blue Ridge Mountains. The King Family Vineyards even hosts polo matches, making wine-tasting an unexpectedly upscale yet casual affair.

The town’s craft beer scene also adds a unique touch, as does Mint Springs Valley Park, where you can fish or picnic in an idyllic mountain setting. It’s the perfect blend of elegance and small-town quirk.

Bedford

Bedford’s quirkiness comes from its dual focus on history and natural beauty. The National D-Day Memorial honors the town’s solemn connection to World War II while standing against the stunning backdrop of the Peaks of Otter, a series of three mountain peaks.

Adding to the charm is the Elks National Home, which transforms into a dazzling Christmas wonderland each year, drawing visitors for its quirky holiday display. Bedford’s small-town Americana vibe makes it delightfully distinctive.

Luray

Luray is quirky thanks to its subterranean wonders. The Luray Caverns house the Great Stalacpipe Organ, a bizarrely fascinating instrument that uses the caverns’ stalactites to play music.

Above ground, the quirk continues with Luray’s charming main street and proximity to Shenandoah National Park. It’s a town where you can explore both the depths of the earth and the heights of the Blue Ridge Mountains in one day.

Urbanna

Urbanna’s quirkiness lies in its dedication to oysters. Its annual Urbanna Oyster Festival transforms the tiny town into a bustling hub of seafood lovers and quirky celebrations, complete with parades and shucking contests.

The town’s colonial-era architecture, like the Old Tobacco Warehouse, gives it a unique historical backdrop. Paired with its waterfront charm, Urbanna is a delightful blend of history and festivity.

Wytheville

Wytheville’s quirkiness stems from its unexpected attractions. It’s the birthplace of Edith Bolling Wilson, a First Lady who some say unofficially acted as president when Woodrow Wilson fell ill. The town proudly celebrates her legacy with a dedicated museum.

For a truly quirky experience, the Wohlfahrt Haus Dinner Theatre combines Broadway-style performances with Southern cuisine. Add in the panoramic views from Big Walker Lookout, and you have a town that’s both scenic and surprising.

9 Hilarious Virginia Town Names That’ll Make You LOL

Image Credit: PeopleImages.com – Yuri A/Shutterstock.com.

PSA: Read this where you won’t embarrass yourself laughing. Whether you’re a Virginia local or just passing through, these town names are sure to make you chuckle when you see them.

9 Hilarious Virginia Town Names That’ll Make You LOL

Most to Least Expensive States To Retire

Photo Credit: Jade Maas/peopleimages.com via stock.adobe.com.

Are you hoping to settle down in a cheaper state than Virginia during retirement? These are the states to consider and, equally important, those you’re better off avoiding.

Most to Least Expensive States to Retire Ranked From 1 to 50

Similar Posts

Leave a Reply

Your email address will not be published. Required fields are marked *