10 Storybook Towns In Virginia
The Commonwealth of Virginia is a rich tapestry of American history. It played a critical role in shaping the country's destiny as one of the original thirteen colonies and home to many of the Founding Fathers. Besides its captivating backstory, the Old Dominion is known for its geographical diversity, hosting an array of stunning landscapes, from Chesapeake Bay to the Appalachian Plateau. Virginia also harbors an impressive collection of vibrant small towns that epitomize the state's true culture and character.
Beyond the chaotic urban scene in cities like Richmond and Virginia Beach, travelers can find charismatic communities with a relaxed pace and stunning natural environments. From coastal getaways like Cape Charles to Shenandoah Valley sweet spots like Luray, here are 10 storybook towns in Virginia to visit in 2025.
Clarksville
Clarksville is a beautiful waterfront village in Mecklenburg County with a relaxing atmosphere, promising guests delightful moments by the lake. It offers a range of outdoor activities at Occoneechee State Park, which sits on the scenic shores of Buggs Island Lake. This recreational hub accommodates picnickers, boaters, fishermen, hikers, and horseback riders across its 2,600-acre territory. Later, guests can unwind with a glass of wine at Three Sisters of Shiney Rock Winery. This family-run establishment specializes in crafting local, native fruit and grape wines.
The Clarksville Regional Museum preserves a collection of historically significant exhibits about the town and its surrounding region. Meanwhile, tourists can get a vivid picture of the early days at Prestwould Plantation. The museum holds one of the country's largest collections of writings by enslaved people and one of the earliest known slave quarters in the South. The 18th-century mansion is one of the most intact plantations in southern Virginia and maintains many of its original elements.
Cape Charles
This adorable fishing village on the Eastern Shore boasts a combination of pristine beaches, unmissable festivals, and classic Chesapeake Bay cuisine. Visitors are lured by its serene natural surroundings, with a chance to isolate on the powdery sands of Kiptopeke State Park. This tranquil coastal escape draws boaters, kayakers, campers, and hikers throughout the year. The Cape Charles Crabby Blues Festival welcomes guests to indulge in its famed crab dishes and celebrate a popular annual tradition with artisan and food vendors, live music, and fun for the whole family.
Historians can learn curious facts about the community's past at the Cape Charles Museum, depicted using a diverse library of photographs, archives, and artifacts. Elsewhere, art enthusiasts can spend quality time inspecting paintings, drawings, and sculptures by amateur and professional artists at the Ellen Moore Gallery.
Ashland
Ashland is a pleasant escape from Richmond, which sits just 16 miles south, and boasts a lively downtown district with numerous points of interest. Exploring its pedestrian-friendly streets opens doors to an immersive cultural experience at the Ashland Theatre. This entertainment hub hosts captivating performances, special presentations, and first-run movies in a family-friendly setting. Alternatively, you can embrace a history lesson at the Ashland Museum, charged with collecting, preserving, and showcasing vital artifacts about Ashland's history.
Ashland also hosts the annual Ashland Strawberry Faire each June, a community celebration and fundraising event for local non-profit organizations that began in 1982. Lastly, outdoor lovers will want to escape to Pufferbelly Park, where two playgrounds, picnic tables, walking paths, and a skate park provide plenty of opportunities for an afternoon of family fun.
Onancock
Onancock is a charming village on the eastern shore of Chesapeake Bay, known for its picturesque historic district and water access. Several historical markers line the downtown to remind newcomers of Onancock's longstanding heritage. Ker Place is a good example and stands out for its red-brick Federal-style construction, which dates back to 1799. While exploring the historic corridor, you can stop to catch a live show at the North Street Playhouse. The venue is a beloved community hub for theatrical productions by skilled local performers.
Art connoisseurs can also find intimate paintings to check out at the Danny Doughty Gallery, which showcases the works of an award-winning local visionary artist. Beyond the town square, vacationers can hop a ferry to Tangier Island, or book a private charter to admire the pristine waters of Chesapeake Bay at your leisure.
Winchester
This Shenandoah Valley borough impresses guests with its charismatic old town district, which hosts a vibrant combination of museums, restaurants, shops, and galleries. Noteworthy historical markers in Winchester include Stonewall Jackson's Headquarters, a Gothic Revival mansion that housed the operations of the Civil War general in the early 1860s. Also, the Museum of the Shenandoah Valley stores vast exhibits chronicling the history of the broad region in a former plantation.
Besides history, guests can live in the moment with engaging, live stage presentations at the Bright Box Theater. This performance venue hosts everything from dance and plays to musicals and comedy shows. Others will prefer a bit of retail therapy at Apple Blossom Mall, home to dozens of brand-name retail stores, a movie theater, and eateries.
Vienna
Vienna is easily one of the most storybook towns in Virginia to check out, thanks to its array of world-class attractions. It is home to the Wolf Trap National Park for the Performing Arts, a 117-acre parkland dedicated to live performances. The 7,000-seater venue hosts engaging musicals, orchestras, and other events that draw crowds year after year. Nature lovers are equally drawn to Meadowlark Botanical Gardens, which features 95 acres of lush greenery with woodland trails inviting guests to admire native plant collections and ornamental garden displays.
Meanwhile, the Freeman Store and Museum provides a pleasant perspective of yesteryear through a permanent collection of period artifacts, photographs, and furnishings. After a fulfilling day of adventure, unwind with a pint of craft beer at Caboose Brewing Company & Tavern.
Chincoteague
This Eastern Shore gem charms first-timers and seasoned travelers alike with its natural beauty, punctuated by pristine beaches and diverse wildlife. Chincoteague provides access to the peaceful Chincoteague National Wildlife Refuge. This island paradise harbors a rich ecosystem of sand dunes and maritime forests, and is distinguished by a herd of wild ponies that roam the shoreline. Visiting families can make memories at Maui Jack's Waterpark, where water slides, lazy rivers, kiddie pools, and tiki cabanas ensure fun for all ages.
Chincoteague has a rich heritage that newcomers can explore at the Museum of Chincoteague Island. Its library of artifacts provides a glimpse of the community's evolution dating back to pioneer days. The same is true for Captain Timothy Hill House, which has the distinction of being the oldest house on Chincoteague Island.
Staunton
Between exploring presidential history and watching world-class stage shows, Staunton ensures your itinerary is lined with unforgettable experiences. This delightful town is known for being the hometown of President Woodrow Wilson. Today, visitors can learn about the president's younger days and rich legacy at the Woodrow Wilson Presidential Library & Museum. Gypsy Hill Park is a highlight for recreation and leisure activities, offering over 200 acres of green space with amenities like a playground, pond, pool, and sports facilities.
Staunton has a vibrant arts community as well, which welcomes you to join fellow theater lovers at the Blackfriars Playhouse for classic Shakespeare in a Renaissance-style venue. Alternatively, the R.R. Smith Center for History and Arts has galleries, a library, studios, and more.
Luray
Luray is a quaint little town in the Shenandoah Valley with a winning mix of historical allure and natural beauty. Historians can get a unique look into the town's pioneer days by touring the Shenandoah Heritage Village. This rustic complex features a collection of vintage structures and gardens that replicate an 1800s settlement, complete with period artifacts and antiques. The Hawksbill Greenway provides an avenue for exploring the town's natural neighborhood along a paved route stretching past picnic areas, ponds, bird habitats, and Hawksbill Creek.
The Luray Caverns are a must-see for visitors to the town. The site consists of a series of caves that open up to stunning chambers with incredible crystalline formations. Visitors can enjoy the spectacle during a guided underground tour.
Williamsburg
Williamsburg transports visitors to the height of Virginia's colonial era. This unassuming municipality served as the colony's capital from 1699 to 1780, and Colonial Williamsburg, the world's largest living-history museum, paints a vivid picture of the period. This preserved 300-acre complex contains old structures, homes, and shops with performers clad in period attire, offering an authentic feel for the nation's formative years. A tour of the Governor's Palace provides an inside look at how the initial governors and royals lived in opulence.
Guests can also browse a vast collection of British and American antiques, classic art, and contemporary art at the Art Museums of Colonial Williamsburg, which offer free admission year round. Elsewhere, Busch Gardens promises a change of scenery with a 400-acre amusement park with roller coasters and thrill rides for the whole family.
Final Thoughts
The above storybook towns in Virginia are a true reflection of the state's diverse culture, history, and natural surroundings. Together, they provide a glimpse into a slower, more enchanting way of life. From the colonial elegance of Williamsburg to the main street magic of Winchester, each town tells its tale in a distinct manner. Whether you're seeking scenic getaways, rich history, or welcoming small-town vibes, Virginia’s hidden gems promise unforgettable experiences that feel like stepping into a fairytale in the United States.
