6 Fairy-Tale Small Towns In Virginia

As a child, it was easy to use your vivid imagination to create a magical realm. Hours could fly by as an imaginary tale unfolded. But as time passes, it becomes harder to find those moments of fairy-tale magic in everyday life. However, that does not mean the fairy tale is gone. In fact, you might be surprised to learn that pieces of that enchantment still exist, right here in the heart of Virginia. The following six destinations bring that spirit back to life, complete with wild ponies, horse-drawn carriages, and wildflower meadows that will awaken the wonder and curiosity of your inner child once again.

Chincoteague

Every fairy tale needs a noble steed, and in Chincoteague, horses bring that magic to life. As a gateway to the Chincoteague National Wildlife Refuge, travelers will have the chance to view the famous herd of wild ponies for themselves. One of the best ways to spot these horses is on an excursion with a reputable tour company. Wild Pony Boat Tours is a highly rated option, offering tours that combine pony and wildlife sightings with local stories, island history, and narration from the boat’s captain.

The wildlife refuge, however, is home to many other majestic species that you should keep your eye out for. With 15 miles of hiking trails, if you decide to explore the refuge at your own pace, you also might be able to spot species like the Delmarva Peninsula Fox Squirrel, bald eagles, herons, and egrets. If you will be in Chincoteague from July 24th through the 26th, check out the town’s annual Chincoteague Blueberry Festival, which has been taking place for 37 years, offering fresh blueberries, blueberry baked goods, and arts and crafts for sale.

Luray

If your fairy tale calls for an underground kingdom, Luray should be your next stop. This town is home to Luray Caverns, the largest cave system in the Eastern United States, featuring cathedral-sized chambers that reach up to ten stories high, each adorned with intricate stone formations. Shenandoah National Park is another destination that feels straight from the pages of a fairy tale, with over 200,000 acres of wooded hollows, wildflower meadows, and cascading waterfalls. Deer, black bears, and songbirds are a few of the friendly species you might see during your time in the park.

At the end of the day, unwind at Castle Vineyards, a wine tasting room and vineyard that has a barn tasting area with board games, billiards, and cornhole, along with an outdoor tasting area that has a large patio, rocking chairs, and a porch swing.

Cape Charles

For the kind of story that ends with a sunset over the water, Cape Charles sets the scene perfectly. This town, located along the Chesapeake Bay, offers plenty of water-based recreation. Visitors can spend an afternoon at Cape Charles Beach, a public beach that borders the historic district, providing calm and shallow waters for families. If you are hoping to explore the town’s shimmering waters, consider arranging a rental with Poseidon Watersports, which has boats, kayaks, and paddleboards for rent.

After a day of swimming or paddling, travelers can head to the Historic Palace Theatre for an art event or show. This theater, which has been operating since 1942, is an excellent example of Art Deco architecture with details like terrazzo floors, ceiling-to-floor mirrors, and walnut paneling.

Williamsburg

While it may not come from a fairy tale, Williamsburg feels like its own world, where cobblestone streets, candlelit taverns, and costumed townsfolk bring history to life. Travelers can experience a piece of this history in Colonial Williamsburg, the world’s largest living museum, featuring costumed actors like George Washington and Gowan Pamphlet, horse-drawn carriage rides, and local artisans demonstrating their craft.

Merchants Square is another way to immerse yourself in this story, an 18th-century-style shopping village with more than 40 local businesses. To admire some colorful and whimsical folk art, spend a few hours at The Art Museums of Colonial Williamsburg, home to several galleries with antiques and art that date all the way back to the 17th, 18th, and 19th centuries.

Warrenton

In the heart of Horse & Wine Country, Warrenton feels like the kind of place where a fairy-tale journey might begin, surrounded by quiet stables, winding vineyards, and open countryside. Each August, Warrenton hosts the Warrenton Horse Show, one of the longest-running horse shows in the country. This year marks its 125th anniversary, running from August 27th through the 31st. The show is open to the public, so be sure to stop by! Hoping to get on horseback yourself? You can sign up for a riding lesson with White Oak Stables, which offers lessons for riders of all ages and levels. Travelers can reward themselves with a glass of wine afterward at Molon Lave Vineyards, a family-friendly vineyard and tasting room that produces an array of boutique reds, whites, and rosés.

Tappahannock

As the fairy-tale journey winds down, Tappahannock offers a fitting final stop, with riverside views, peaceful bed and breakfasts, and seafood feasts. The Rappahannock River Valley National Wildlife Refuge is a must-visit for nature lovers, home to a number of magical species. Depending on the time of year, some of the species you might spot in the refuge include great blue herons, bald eagles, monarch butterflies, white tailed deer, and spotted turtles. There are some great spots in town to grab seafood as well. Bubba’s Shrimp Shack is a nice option, serving fresh crabcakes, fried oysters, steamed shrimp, flounder, and many other seafood favorites. Travelers looking for a place to lodge for the night will love the Essex Inn, a historic home built in 1851 with Greek Revival architecture. For an extra cozy touch, every room has an electric fireplace!

Final Thoughts

Each of the towns above offers a different sort of adventure. Some offer tales filled with rolling vineyards and horseback rides, while others offer seaside escapes with an afternoon on a kayak or canoe. Depending on the time of year, you might even be able to attend one of these towns’ magical festivals! No matter which story has captured your heart, each of these towns offers a chance to feel the magic of the world once again.