13 Offbeat Towns To Visit In Virginia
Virginia has way more to offer than just its famous historical sites and beaches. Tucked away between the Blue Ridge Mountains and coastal plains are quirky small towns with unique personalities all their own.
I’ve explored these hidden gems and found places where you can experience everything from underground caverns to towns seemingly frozen in time. Ready to discover a different side of the Old Dominion?
1. Occoquan: Riverside Charm With Ghost Stories
Ever walked through a 300-year-old town where locals casually mention their resident ghosts? That’s daily life in Occoquan, a riverside hamlet where history and mystery blend perfectly together. The town’s narrow streets are lined with colorful boutiques housed in buildings dating back to the 1700s.
You’ll find everything from handmade jewelry to vintage books. Don’t miss the haunted walking tours where guides share tales of Occoquan’s spectral residents. After dark, grab dinner at one of the waterfront restaurants where you might spot glowing orbs reflected in the river – or so the locals say.
2. Tangier Island: The Floating Time Capsule
Imagine a place where people still speak a dialect similar to Restoration-era English and most transportation happens by boat or golf cart. Welcome to Tangier Island, sitting isolated in the Chesapeake Bay. Getting here requires a ferry ride, immediately signaling you’re heading somewhere special.
The island’s 400 residents primarily make their living crabbing and fishing, continuing traditions passed down for generations. While visiting, try the island’s famous soft-shell crabs at Fisherman’s Corner restaurant. Just remember to plan your visit between May and September, as winter weather often cuts the island off from the mainland.
3. Floyd: Blue Ridge Music Haven
Friday nights in Floyd transform this tiny mountain town into the epicenter of Appalachian music. The famous Floyd Country Store hosts the Friday Night Jamboree where locals and visitors alike stomp their feet to old-time and bluegrass tunes.
During daylight hours, I love wandering through the town’s eclectic mix of artist studios, craft shops, and farm-to-table eateries. The surrounding countryside offers spectacular drives along the Blue Ridge Parkway.
For the full experience, time your visit during FloydFest, a summer music festival that brings together musicians from across the country while maintaining an intimate, family-friendly atmosphere unlike massive commercial festivals.
4. Kilmarnock: Northern Neck’s Hidden Gem
Who would expect a sophisticated art scene and gourmet restaurants in a tiny Northern Neck town? Kilmarnock surprised me with its blend of small-town friendliness and unexpected cultural offerings.
Strolling down Main Street reveals carefully preserved historic buildings now housing art galleries, antique shops, and boutiques. The town punches way above its weight with dining options ranging from fresh Chesapeake seafood to international cuisine.
Make time to visit the Steamboat Era Museum to learn about the vessels that once connected this peninsula to the wider world. Then head to Good Luck Cellars vineyard just outside town for award-winning wines with water views.
5. Smithfield: Ham Town With Historic Heart
If you’ve ever enjoyed a Smithfield ham, you already know part of this town’s claim to fame. What you might not realize is that behind the famous pork products lies one of Virginia’s most perfectly preserved colonial towns.
Walking through Smithfield feels like stepping into a living museum, with over 70 buildings dating from the 1700s and early 1800s. The wharf area along the Pagan River offers scenic views that haven’t changed much in centuries.
While here, I recommend touring the Isle of Wight Museum to see the world’s oldest Smithfield ham (dating to 1902!) and sampling modern ham creations at local restaurants that have elevated the town’s signature product to an art form.
6. Clifton Forge: Railroad Town Revival
Nestled in the Allegheny Mountains, this former railroad boomtown has reinvented itself as an arts destination. The transformation of Clifton Forge from fading industrial center to creative hub happened through sheer community determination.
The heart of town houses the Clifton Forge School of the Arts, offering classes in everything from blacksmithing to fiber arts. The restored Masonic Theatre, dating to 1905, now hosts performances ranging from bluegrass concerts to independent films.
Between cultural activities, explore the town’s railroad heritage at the C&O Railway Heritage Center. For outdoor enthusiasts, nearby Douthat State Park offers mountain biking trails and a lake perfect for swimming during summer months.
7. Chincoteague: Island of Wild Ponies
Made famous by the children’s novel “Misty of Chincoteague,” this barrier island offers much more than just its legendary wild ponies. Though watching those majestic creatures swim across the channel during the annual Pony Swim remains an unforgettable experience.
The island moves at its own relaxed pace, with no high-rises or chain stores to disturb the coastal village atmosphere. Fresh seafood stands dot the roads, offering just-caught oysters and crabs. Beyond pony-watching, kayaking through marshlands reveals abundant bird life, while Assateague Island National Seashore provides miles of pristine beaches.
Don’t leave without trying the famous Chincoteague oysters – salty and sweet thanks to the unique local waters.
8. Abingdon: Theater and Trails
Have you ever watched professional theater in a 1933 art deco building, then hopped on a bike to ride along a converted railroad bed? In Abingdon, these contrasting experiences create the town’s unique appeal.
The famous Barter Theatre (where actors once performed for food during the Depression) anchors Abingdon’s thriving arts scene. After a show, browse the galleries and craft shops lining the 20-block historic district filled with Federal-style buildings. For outdoor enthusiasts, the Virginia Creeper Trail begins here, offering 34 miles of scenic biking through mountains and alongside streams.
Most visitors opt for the downhill section from Whitetop Mountain, with shuttle services making the experience effortless.
9. Onancock: Eastern Shore’s Perfect Port
Halfway up Virginia’s Eastern Shore peninsula sits Onancock, a waterfront town where three creeks converge before flowing into the Chesapeake Bay. The name comes from a Native American term meaning “foggy place,” though today’s visitors find the atmosphere anything but unclear.
The town’s harbor welcomes kayakers and sailors, while the historic district features buildings spanning three centuries. Market Street offers a delightful collection of restaurants, galleries, and the charming Roseland Theatre showing both mainstream and independent films.
My favorite activity here is taking a boat tour to Tangier Island or exploring the creeks by kayak. Afterward, enjoy dinner at one of the waterfront restaurants serving the Eastern Shore’s famous oysters and blue crabs.
10. Wachapreague: Seaside Fishing Village
Known as the “Little City by the Sea,” Wachapreague delivers big experiences for fishing enthusiasts and nature lovers. This tiny Eastern Shore town (population under 200) becomes a bustling hub during fishing season when anglers arrive seeking the legendary offshore catches.
The town’s protected harbor fills with charter boats heading out to some of the Atlantic’s richest fishing grounds. Even if you’re not into fishing, the surrounding marshlands offer spectacular kayaking and bird watching opportunities. When hunger strikes, the Island House Restaurant serves seafood so fresh it was likely swimming that morning.
For the full experience, book a stay at one of the historic inns and wake up to views of the sun rising over the barrier islands.
11. Clintwood: Heart of Appalachian Music
Tucked away in Virginia’s southwestern corner, Clintwood preserves the authentic sound of Appalachian music. The Ralph Stanley Museum honors the legendary bluegrass musician who called this region home, with interactive exhibits that trace the evolution of mountain music.
Beyond music, the town serves as gateway to the spectacular Breaks Interstate Park, known as the “Grand Canyon of the South.” The five-mile gorge carved by the Russell Fork River offers breathtaking views and hiking trails for all skill levels.
When visiting, time your trip for the Ralph Stanley Bluegrass Festival held each May. You’ll hear musicians playing in styles passed down through generations, creating an authentic cultural experience you won’t find in more touristy destinations.
12. Sperryville: Gateway to the Shenandoah
At the foot of the Blue Ridge Mountains sits Sperryville, a tiny town that packs an outsized culinary and artistic punch. What was once just a waypoint for Shenandoah National Park visitors has transformed into a destination in its own right.
The town’s main street features restored historic buildings now housing art galleries, craft shops, and farm-to-table restaurants. Copper Fox Distillery produces award-winning whiskey using local ingredients and traditional methods you can witness during their fascinating tours.
I suggest making Sperryville your base for exploring nearby Shenandoah National Park. After a day of hiking, return to town for a meal at one of the restaurants serving ingredients sourced from surrounding farms, followed by live music at a local venue.
13. Irvington: Tidewater Luxury in Miniature
Situated on a peninsula between the Rappahannock River and Carter’s Creek, Irvington combines small-town charm with unexpected sophistication. The town’s maritime heritage is evident everywhere, from the Tides Inn resort to the numerous sailboats dotting the harbor.
King Carter Drive features boutiques, galleries, and the Historic Steamboat Era Museum chronicling the vessels that once connected this region to Baltimore and Norfolk. For wine enthusiasts, the Dog and Oyster Vineyard pairs local wines with freshly harvested Chesapeake Bay oysters.
Though tiny, Irvington hosts impressive events like the Chesapeake Academy Auction and the Irvington Farmers Market. For the ultimate experience, time your visit to coincide with the town’s quirky Thanksgiving Turkey Trot, where costumes are as important as running speed.