6 Most Unconventional Towns In Virginia
When the “Old Dominion” famously adopted the slogan "Virginia is for Lovers" back in 1969, few could have predicted that this catchy phrase would have caught on and still be in use today. One of America’s best-known tourism catchphrases, it says as much about the state’s charm as it does about its sometimes unconventional character.
This is especially true of Virginia’s smaller towns, many of which have embraced their less conventional attractions and landmarks and turned them into exciting experiences. From a gas station-turned-dining spot to walking in the footsteps of revolutionaries, these six lovely towns in Virginia stand out for their unique blend of historic landmarks, quirky attractions, and local culture.
Winchester
Considered the gateway to the beautiful Shenandoah Valley, Winchester is one of the most walkable towns in Virginia. Start your visit in Old Town Winchester, a quaint 45-block district centered around the Loudoun Street Pedestrian Mall. This historically significant, brick-paved street features many well-preserved old buildings and attractions, including the Shenandoah Valley Civil War Museum, housed in an 1840s courthouse. It’s also only a short stroll away from important landmarks like George Washington's Office, a modest wood cabin where the future (and first) president planned the Valley’s defences in the mid-1700s.
You’ll also want to visit the Museum of the Shenandoah Valley, a fascinating attraction which combines regional art, history, and seven acres of stunning gardens to explore. Stop for a traditional Southern breakfast at Bonnie Blue, a former gas station turned diner and grab a handcrafted sandwich at Knead Bread bakery (both are close to the Old Town area). Country music fans won’t want to miss the Patsy Cline Historic House, the childhood home of the legendary singer, preserved to reflect her humble beginnings. End the day in comfort at The George Washington Hotel, a grand old property built in 1924 in the heart of downtown Winchester.
Luray
You’ll find Luray’s most unconventional attraction deep underground. The Luray Caverns, the largest cave system in the eastern United States, is the star attraction here and draws visitors year round. Discovered in 1878, in addition to seeing its towering stalactites, stalagmites, crystal clear pools, and even the original steep stairs from the 19th century, you’ll see (and hear) the hauntingly beautiful Great Stalacpipe Organ, an unusual instrument which produces musical notes from the cave formations.
Afterwards, head across the road to nearby Carillon Park. Built in 1937 and dubbed the Luray Singing Tower, this 117-foot “landmark to love” was built as a memorial to the wife of a former owner of the caverns. It’s at its most magical during regularly scheduled recitals which put its 47-bell carillon through its paces. For accommodations, I recommend the Mimslyn Inn for its blend of vintage charm and modern comfort. Built in 1931, this stately property provides an elegant retreat after a day of exploration.
Williamsburg
Colonial Williamsburg is certainly impressive. Covering a whopping 301 acres and ranked the world’s #1 living history museum, this unique immersive experience takes you back to the pre-independence days of the early 18th century. Highlights include walking along Duke of Gloucester Street, a thoroughfare lined with reconstructed and original buildings including the Governor’s Palace, built in 1722 when Williamsburg served as the first state capital from 1699 to 1780; and the lovely Bruton Parish Church, dating back to 1715 (check out its memorable candlelight concerts).
For a truly immersive experience, book a stay at one of the Colonial Houses Historic Lodgings. Managed by the luxurious Williamsburg Inn, this unique collection of 26 restored buildings from the 1700s offers awesome (and unconventional) accommodations. My stay at Dr. Barraud’s Kitchen Forge meant I was less than a five-minute stroll from the iconic King’s Arms Tavern with its traditional fare from colonial times (try the Peanut Soup… wow!).
Front Royal
One of a handful of charming small towns that serve as excellent bases from which to explore Shenandoah National Park, Front Royal is a blend of historic charm, quirky attractions, and outdoor adventures. Start your visit with a stroll through the picturesque downtown area and have your camera ready for great photos of the 1911 Gazebo on Main Street, and the Front Royal/Warren County Visitors Center, set in a former railway station. My favorite downtown attraction? The Virginia Beer Museum is dedicated to the history of beer in the Commonwealth with vintage brewing equipment and an impressive selection of Virginia craft beers to sample. The nearby Vibrissa Beer is another great waterhole and offers beer flights and good grub.
Just minutes from town, Skyline Drive winds through 105 miles of breathtaking scenery in Shenandoah National Park. Join this route and head south from Front Royal and you’ll enjoy a few hours exploring a beautiful section of the Blue ridge Mountains. Notable stops include the Dickey Ridge Visitor Center, which provides exhibits and trail maps, and the Fox Hollow Trail for a hike past the remnants of old homesteads.
Charlottesville
It’s not by chance that Charlottesville is considered the best college town in Virginia. A wonderful blend of academia, art, and history, topping my list of favorite things to do in Charlottesville is wandering the grounds of University of Virginia. Designed by Thomas Jefferson, the centerpiece of this UNESCO World Heritage Site is the fabled Lawn. This vast green space leads to the Rotunda, completed in 1828 and still in use today as a visitor center. Be sure to also include Monticello on your Charlottesville itinerary. Built by Jefferson between 1769 and 1809, admission to this architectural masterpiece is via a dedicated tour. Afterwards, grab lunch at Michie Tavern, a 1 building from 784 that serves authentic colonial-era meals.
Other Charlottesville highlights include the pedestrians-only Downtown Mall with its live music, artisan shops, and cafés, and for an artsy twist, Ix Art Park and The Looking Glass offer up a decidedly unconventional and interactive art experience. The Kluge-Ruhe Aboriginal Art Museum is also worth visiting and provides a unique perspective on Indigenous Australian art. Where to stay? The charming Oakhurst Inn, a boutique property within walking distance of the university, is my #1 choice. And for a wonderful place to binge on fresh baked sweet and savoury treats, add the wonderful Cou Cou Rachou to your list of places to eat.
Yorktown
Yorktown’s Revolutionary War roots make it a must-visit. Begin your exploration at the Yorktown Battlefield where the British, under General Cornwallis, surrendered in 1781. The Yorktown Victory Monument, completed in 1884, is just a stroll away and commemorates this pivotal event. You can learn more about this period in US history at the nearby American Revolution Museum at Yorktown with its interactive exhibits and outdoor reenactments.
Be sure to explore the Yorktown waterfront, home to shops and eateries, and book a sightseeing sail on a schooner along the York River. When you’re done, follow the scenic Colonial National Parkway to Historic Jamestowne, the first permanent English settlement in America. Established in 1607, you’ll even catch archaeologists at work digging up more clues to the nation’s early history.
The Final Word
A visit to some of Virginia’s most unconventional towns is a great way to get to know this beautiful part of the South. Whether it’s exploring massive underground caverns or walking in the footsteps of revolutionaries, each of these destinations offer something truly unique. Round off your experience with a stay at a historic inn, a meal at a quirky eatery, or a wander on an old brick-lined road, and you’ll find out why these six most unconventional towns in Virginia are so much fun to explore.
