10 Quirkiest Virginia Towns To Visit In 2025
The Old Dominion of Virginia may be best known for being the “Mother of Presidents” and a state at the epicenter of United States history, but there’s far more to Virginia than meets the eye. You can tour the historic home of the nation’s first president, and you can find a rare bald eagle habitat and a uniquely storied whiskey distillery nearby. Explore the “birthplace of country music,” enjoy some traditional tunes at an authentic country home, and indulge in contemporary luxury at a farm resort. Head down to the beach for an idyllic day at the shore, and see the place that inspired one of the nation’s most beloved children’s books.
From the rugged heights of the Appalachians to the tranquil shores of Chesapeake Bay, here are 10 of the quirkiest Virginia towns to visit in 2025.
Bristol
Located at the Virginia-Tennessee state line, Bristol is the mountain town with a lofty place in American music history and culture. Often called the “birthplace of country music” thanks to the 1927 Bristol Sessions that essentially turned some local folk musicians into major pop stars, you can explore more of Bristol’s musical heritage at the Smithsonian-affiliated Birthplace of Country Music Museum in town. For some more up-to-date country music, along with plenty more special performances, catch a show at the Paramount Bristol. And if you seek the ultimate country-style throwback, drive out to the Carter Family Fold, a very special historic home and concert hall in the mountains that’s still run by the “first family of country music” and hosts a variety of country, bluegrass, and folk musicians for weekend performances.
Though Bristol maintains much of its traditional grit that continues to draw old-school country music fans to town, there’s another side of Bristol awaiting your discovery at Nicewonder Farm & Vineyards. Here, you can taste an astounding array of award-winning, locally made wines, including Viognier, Chardonnay, Petit Verdot, and Cabernet Franc, and pair them with delectable food from Hickory Fine Dining. In addition, you can book a tee time at the prestigious Tom Fazio-designed Virginian Golf Club, enjoy a Swedish-style massage at the spa, and simply revel in the elegance of your room, suite, or luxury yurt on property.
Galax
When’s the last time you visited a national park for concerts? Yes, really, this town at the edge of the Blue Ridge Mountains keeps the hills alive with the sounds of traditional folk and Americana music. More specifically, Galax is located along the National Park Service-run Blue Ridge Parkway, which itself makes for an incredibly beautiful drive between Shenandoah National Park and Great Smoky Mountains National Park (in North Carolina). But while you’re here, make sure to stop at the Blue Ridge Music Center to peruse the exhibits of the American Music Museum, learn more about the origins of bluegrass and American folk music, and wander along the gorgeous wilderness trails outside. And if you’re here during the summer season, don’t miss out on their “Deep Roots, Many Voices” concert series.
If all the great bangers you hear at the Blue Ridge Music Center inspire you to try making music, make a stop at Barr’s Fiddle Shop in town for a real local treasure full of banjos, fiddles, dulcimers, guitars, and other music supplies. To experience more of Galax’s creative spirit, check out the Chestnut Creek School of the Arts, and maybe sign up for a woodworking, glassmaking, or pottery workshop. And whenever it’s time to call it a day, retreat to the lovely New River Trail Cabins and enjoy your own cute and cozy cabin by the picturesque Chestnut Creek.
Meadows of Dan
Also located along Blue Ridge Parkway, about 63 miles north of Winston-Salem (North Carolina), Meadows of Dan is a tiny town with a funny name and a very crafty spirit. Come for Mabry Mill, a historic gristmill built by Edwin Boston Mabry in 1905, where he and his spouse Lizzy would ground corn, saw lumber, and do blacksmithing. Today, you can tour the grounds, see these facilities as they were back in the day, and take in the pleasant mountain views along the way. And if you’re visiting on a Sunday, stick around for live music and dancing.
Though the mill no longer operates as an industrial facility, there’s still plenty of good stuff being made in Meadows of Dan. Stop at Concord Corner Store for a wide selection of locally and regionally made artisan goods and gifts, grab some refreshment and phenomenal local coffee at Primitive Coffee Market, and satisfy your sweet tooth with a stop at Nancy's Candy Company for their famous fudge and other special artisan delights.
Massanutten
A ski resort… in Virginia? Yes, Massanutten Ski Resort really does offer a variety of trails for skiers and snowboarders at all levels during the winter season, and during the summer season Massanutten has a waterpark, golf course, mountain bike trails, and plenty more open to ensure fun times for the whole family. But if you’re looking to explore more beyond the resort, Massanutten also places you right by Shenandoah National Park, an amazing stretch of Appalachian Mountain wilderness with ample opportunities for scenic drives, as well as hikes on nearby trails like South River Falls, Hightop Summit, and Saddleback Mountain.
If you can use some adult refreshment after a long drive or hike through the Shenandoah Valley, head over to Elkton Brewing Company for “creatively crafted small batch” local artisan beers (and live music on weekends!) For a more family-friendly easygoing day, pop over to Lake Shenandoah for a serene fishing lake and two miles of pretty walking trails. Finally, return to Massanutten Resort for a wide variety of accommodations suitable for groups of all sizes.
Luray
If you’ve ever done a road trip to Shenandoah National Park, you may have stopped at the town of Luray to see some caves. Indeed, Luray is home to Luray Caverns, a magnificent network of limestone caves with ten story-tall ceilings, fascinating rock formations, the aptly named dream lake, and its signature Great Stalacpipe Organ. Right next to the caverns is the Shenandoah Heritage Village, a seven-acre re-creation of a 19th century farming village that also includes the Luray Valley Museum and its remarkable collection of historic artifacts.
As noted above, Luray also makes a good launchpad for exploring Shenandoah National Park, including the scenic Skyline Drive that’s wonderful to drive year-round, but is especially great during autumn when the forest explodes in festive fall colors.When you need some rest and relaxation, return to town and check into the Hotel Laurance for a charming and distinctive boutique hotel that’s already making waves far beyond the mountains.
Lovettsville
Lovettsville may only be about 57 miles from the hustle and bustle of Washington, D.C., yet this Northern Virginia town feels a world away from the nation’s capital with its wine country scenery and bon vivant ethos. If you’re visiting late in September, make sure to experience Lovettsville Oktoberfest, which combines classic Bavarian harvest season traditions with signature Southern flair. And if you’d like to try some more local and regional craft beers, 1836 Kitchen & Taproom has you covered.
No matter when you visit, make time for good wine and go with a designated driver to Hiddencroft Vineyards to try their assortment of reds and whites made with their own estate-grown grapes. Also, stop at Domaine Fortier to tour their beautiful vineyards and sample their small-lot, hand-crafted wines. To complete your wine country getaway, do a stay at Stone Manor Boutique Inn, a stunning bed-and-breakfast perched by the mountains that’s a favorite for wedding celebrations.
Mount Vernon
Mount Vernon may have been made famous by a famous first president who allegedly could not tell a lie, but it really is true that this Northern Virginia town (about 19 miles south of Washington, D.C.) offers a whole lot to see and do. Of course, no trip to Mount Vernon feels complete without touring George Washington’s Mount Vernon, the family estate where George Washington lived from 1754 to his post-presidential years. Come to tour the grand Palladian style mansion and the lush gardens, and stay to learn more about the estate and the Washington family at the Donald W. Reynolds Museum.
If you’re a hard-core history buff, mosey over to the nearby George Washington Presidential Library for a deeper dive into the United States’ colonial era and Revolutionary War history. When you can use a break to stretch out and take in some fresh air, drive down to Mason Neck State Park to see American bald eagles in the wild, and to do some canoeing or kayaking on the open Potomac River. For something really special, head back to town to check out George Washington's Distillery® and Gristmill, a loving reconstruction of the original 18th century distillery that makes great whiskey and other small-batch spirits today. And though you have plenty of lodging options in the D.C. metro region, try the Embassy Suites by Hilton Springfield for a comfy place to stay within easy reach of Mount Vernon.
Williamsburg
Is it a historic village? Is it a college town? Is it a place for thrill rides? Yes, Williamsburg is all that and more, and it’s only about 55 miles east of Richmond. Founded in 1632 and established as Virginia’s colonial-era capital in 1699, Colonial Williamsburg is not only well preserved, but welcomes visitors to wander its collection of historic landmarks, including the old Capitol, the Governor’s Palace, Charlton’s Coffeehouse, and the Public Gaol. For even more local history, art, and culture, stroll into the campus of the College of William & Mary, the nation’s second-oldest higher educational institution (founded in 1693), take in the vast variety of works on display at the Muscarelle Museum of Art, and enjoy a quiet moment at a lovely garden area anchored by the Crim Dell Bridge.
While there’s plenty to learn when exploring the historic streets of Williamsburg, this is also a town that really knows how to have fun. More specifically, this town is also home to Busch Gardens Williamsburg, a theme park with an amazing array of roller coasters, classic carnival rides, water rides, animal conservation exhibits, and more. And right by Busch Gardens, you will also find Kingsmill Resort, a wonderfully family-friendly resort with easy access to the theme park along with three 18-hole golf courses, a full-service spa, and even a full-service marina on site.
Tangier Island
Located about 12 miles out in Chesapeake Bay and accessible by boat from Crisfield (Maryland), Tangier Island is a remote and exotic-feeling island escape that’s surprisingly within reach of Washington, D.C., Richmond, and Virginia Beach. As soon as you reach the Tangier Island Marina, you know this is a special place as you watch the fishermen handle their daily catch and the seabirds flying around. From the marina, walk over to the Tangier History Museum to learn about the island’s past, including its time as a military base during the War of 1812 and its role in the development in aviation in the early 20th century. They even have kayaks and canoes available to borrow so you can see more of the island on water!
As an active fishing community, Tangier Island is a prime spot for feasting on the finest locally caught seafood, and Lorraine’s Seafood Restaurant and Four Brothers Crab House are wonderful restaurants to taste the island’s boldest and freshest flavors. Whenever you feel like kicking back, relax and enjoy the easy vibes at Brigadune Inn, a lovely family-run inn perched right by the bay.
Chincoteague
Chincoteague may be another island off Virginia’s Eastern Shore, but this island is the stuff of storybooks. Yes, really, the local legend of Chincoteague ponies inspired author Marguerite Henry to write Misty of Chincoteague, a 1947 children’s novel that was later adapted into a movie in 1961. Every July, you can catch the famed pony swim at Chincoteague National Wildlife Refuge, and year-round you can spot native wildlife like bald eagles, ghost crabs, monarch butterflies, and snow geese. In addition, the refuge has some 15 miles of hiking trails and a pristine Atlantic Ocean facing beach open to the public.
For a deeper dive into Misty’s lore and backstory, head over to Beebe Ranch to meet some local horses and learn about the real-life story behind the novel. Also check out the Museum of Chincoteague Island for more Misty history, and stay to view artifacts left over from past shipwrecks, the 1st Order Fresnel Lens from the Assateague Island Lighthouse, and many more historic documents and records. Speaking of the Assateague Island Lighthouse, you can visit this historic lighthouse (completed in 1867) that continues to guide ships toward safe harbor on the neighboring island. Whenever you’re ready to call it a day, check into BluFin Bungalows & Marina, relax in your own waterfront bungalow, and take in the gorgeous bay and marina views.
These Virginia Towns Are So Quirky and So Much Fun
The Commonwealth of Virginia may be best known for its rich and momentous history, but it’s also a state with a curiously quirky side, and it’s a state that knows how to have fun. At Bristol, dive deep into the history and culture of bluegrass and country music. At Meadows of Dan, explore the rugged past of Appalachia and find a surprising haven of contemporary luxury. At Lovettsville, find a town that blends Bavarian tradition with down-home Southern flavors and flair. And at Chincoteague, step into a charming storybook coastal village where the ponies continue to run free. Virginia has quite a few funky and quirky towns, and these quirky towns have some of the state’s best hidden treasures awaiting your discovery.
