13 Cutest Small Towns In Virginia
The state of Virginia has a natural charm that extends well beyond its booming metropolises and the wealth of historic monuments and landmarks. Whether you are near the Blue Ridge Mountains or the Chesapeake Bay, the Commonwealth is filled with small towns that capture the essence of southern hospitality and colonial heritage, dating back centuries beyond the American Revolution. In the 2025 edition of the Cutest Small Towns in Virginia, you will be introduced to, or reintroduced to, 13 communities that embody simplicity and small-town, adorable life. Whether it is the apple orchards in Lexington or the Victorian elegance of Cape Charles, these are the cutest and most enchanting places that you can visit in Virginia.
Staunton
This small town is enchanting to visitors for its preserved Victorian architecture and thriving arts scene. Famously, it is the birthplace of President Woodrow Wilson and still features more than 200 buildings designed by famed architect T.J. Collins. The abundance of these buildings creates an atmosphere that feels as though it were pulled from the 1800s.
The American Shakespeare Center's Blackfriars Playhouse is the only accurate reconstruction of Shakespeare's famous indoor theater. Here, you can see year-round performances in this intimate setting, illuminated only by candles and chandeliers. To learn more about the town’s most famous resident, you can stop by the Woodrow Wilson Presidential Library and Museum to find out more about the 28th president's life through the restored building where he was born. If the exploration has left you hungry, this cute little town has plenty to offer in the way of dining. For authentic farm-to-table southern cuisine in a restored historic firehouse, check out Zynodoa.
Abingdon
When you head over to the mountainous expanse of southwestern Virginia, you can likely encounter the small town of Abingdon. This place is a true blend of charming community spirit and Appalachian heritage. The best expression of this is historic Main Street, with its 19th-century buildings filled with galleries, boutiques, and restaurants. One of the popular stops in this bustling part of the community is Chellas on Main, which offers an eclectic assortment of merchandise, from crafts to ceramics.
Barter Theatre, which claims to be the nation's longest-running professional theater, hosted early performances by notable actors such as Ernest Borgnine and Gregory Peck. One of the things that makes this town so unique is its preservation of history, as exemplified by the charming eatery The Tavern, which serves upscale fare in one of the region’s oldest buildings, dating back to 1779.
Lexington
Despite being home to Washington and Lee University and the Virginia Military Institute, Lexington strikes a balance between its youthful energy and a quiet, historically grounded charm. This town appears to have been plucked right from the colonial era, with brick sidewalks and gas-lamp streetlights that suggest horse-drawn carriages are far from out of place. Celebrating this history is not difficult, and your tour should begin at the Lee Chapel and Museum, which features Robert E. Lee's office, preserved to reflect its historical appearance. You should also visit the Virginia Military Institute Museum, which celebrates a legacy spanning over 180 years of military operations and evolution throughout America's history.
Natural beauty is also one of the elements that make Lexington so cute for visitors, and Goshen Pass best accentuates it. This is where the Maury River slices through the mountains, creating picturesque landscapes and ample opportunities for water recreation.
Middleburg
Middleburg has become renowned for being the capital of horses and hunting, truly embodying Virginia's rich equestrian heritage. Not only is it famous for its horses and illustrious history of fox hunting, but it is also situated squarely in Loudoun County's wine country. Everything about the charming town exudes timeless grace and old wealth. To take a closer look at this celebrated history of field sports and racing, take a moment to visit the National Sporting Library & Museum.
When you are ready to unwind and take a stroll through the gorgeous landscapes, you should book a tour of the Boxwood Estate Winery. Cap off your experience in one of rural Virginia's most charming towns by eating at the Red Fox Inn & Tavern, which has been operating continuously since 1728, making it one of America’s oldest inns.
Smithfield
The name Smithfield has long been synonymous with premium hams shipped worldwide. Sitting on the Pagan River, the town continues to look remarkably like it belongs in the 17th or 18th century, with more than 60 buildings from this era lining the main thoroughfare and streets of the community. A good example of this is St. Luke's Church, believed to have been built around 1632, and one of the nation’s oldest English-founded churches still standing.
To get an even better look at the colonial homes and expansive gardens typical of many of the properties in Smithfield, one should begin their tour of the town at the Smithfield & Isle of Wight Visitors Bureau to schedule a walking tour among the area’s most attractive estates. If you have not gotten your fill of the ham the quaint community is known for, take in farm-fresh options for lunch at the Taste of Smithfield Restaurant, operating out of a cute downtown storefront.
Cape Charles
If you want to feel like you walked into a time capsule from the Victorian Age, you should take the time to visit the eastern shore community of Cape Charles. One of the most noteworthy attractions in this quaint little town is the free Cape Charles Beach along the Chesapeake Bay. The city is also very walkable, with grid streets that allow you to stroll past numerous historic, colorful homes that showcase the coastal vibe.
If you want to learn more about the history of this cute community, take a moment to visit the Cape Charles Museum & Welcome Center. Not only will you get a glimpse into the evolution of the town, but you will also get the deep railroad history that the community was once known for. When you are ready for a bite to eat, locals love The Sunset Beach Bar and Grille, which serves quick fried and coastal cuisine right along the water.
Floyd
One of the things that makes Floyd so attractive and charming in Virginia goes beyond its location amid the Blue Ridge Mountains. This town has become synonymous with Virginia's music and arts scene, and you will find multiple places offering weekly jam sessions, as well as quaint and quirky eateries like OuterSpace, which boasts eclectic outdoor seating. The creative community here welcomes artists and creators from all corners of the world.
One example of the jam sessions happens every Friday night at the Floyd Country Store. There, you will find locals dancing to authentic mountain music. To further accentuate the companionship with the arts, visitors should check out the Jacksonville Center for the Arts, which showcases the work of regional artists.
Occoquan
The small community used to be a mill town, with its strategic placements along the river of the same name. Today, Occoquan has become an arts and antiques destination without entirely losing its 18th-century charms. The main thoroughfare, called Mill Street, angles down to the river and remains lined with shops and historic buildings. Some of the popular boutiques among the more than 100 artisan shops and galleries throughout the town include Man Overboard, a destination for antiques known for its varied selection.
The town has become a place that is as rich in history as it is in delicious food. Take a look at the Mill House Museum for a heavy dose of global history in a building that has stood here since 1790. When you have built up an appetite, the locals here tend to enjoy a meal at Madigan's Waterfront, known for delicious dishes of American cuisine with seating overlooking the river.
Urbanna
A town at the confluence of the Rappahannock River and the Urbanna Creek, the small village thrives on its fishing and oyster industry, dating back to the late 1600s. Its position along the water, along with its historic homes, makes it one of the quintessential walks back in time to Virginia's colonial era on the Middle Peninsula.
When you see the schoolhouse in town, built in 1850, you will soon realize it is the Urbanna Museum & Visitor Center. This details the region's long maritime history, whereas a stroll along the active Urbana Creek might show you the current state of the industry, with working vessels and boat slips. To further celebrate the deep-rooted industry of oystering, you should plan your visit around November to appreciate the Urbanna Oyster Festival. This event celebrates the heart of the town and draws in thousands.
Washington
When you travel around the country, there are no shortages of towns and cities named after the United States’s first president, George Washington. This Washington, however, is the first of its kind and was in fact surveyed for development by the man for whom it is named back in 1749. The community is one of the smallest in the state of Virginia. Still, it has a deep history of refined food and wine while maintaining a look and feel that appears very much plucked from Colonial America.
Natural wonders continue to turn heads today, just as they did for the original founding father, with Washington serving as a gateway to Shenandoah National Park via Skyline Drive. You would not think that such a small and quiet town would have a fine dining establishment rated with three Michelin stars, but The Inn at Little Washington is just that. Similarly, the Theatre at Washington here is active despite the town’s size, offering professional performances in a very intimate setting.
Onancock
Much like Cape Charles, Onancock has a maritime character due to its location along the Eastern Shore of Virginia. The Chesapeake Bay is home to a diverse range of individuals, from artists to retirees, making the town both culturally rich and historic, with its deep-water harbor serving the area since the 1600s. An attractive component of the quaint little community is the Onancock Wharf, where you can appreciate a gorgeous sunset amid the many working vessels and boats docked here.
History is an integral part of what makes the community so charming, and a key element in this is one of Virginia’s oldest operating general stores, Hopkins & Brothers Store, which has been serving this community since 1842. When you are looking to grab a memorable bite to eat, do not miss out on the fresh catch dishes happening at Mallards at the Wharf.
Warrenton
Civil War history is what Warrenton is best known for, particularly in its historic Old Town. This district features numerous preserved buildings from the 18th and 19th centuries, adding a unique charm to the community; it cannot be replicated in places like nearby Washington, D.C. One of the places to stop and visit on your trip here is the Old Jail Museum, constructed in 1808. This building has served as a jail for over 160 years. There are also numerous Civil War-era battlefields surrounding the town, offering a deep dive into one of the country’s most tumultuous periods.
It is not hard to look around and see the beauty and wonder that Warrenton has to offer, particularly at the Airlie Center, a stunning estate with lush gardens and trails for peaceful reflection. In a similar vein, make sure to grab a bite at the popular Alias for an intimate atmosphere and delicious upscale cuisine.
Chincoteague
One of the obscure things that Virginia has become famous for is a small piece of land, Chincoteague Island, where wild ponies run free. You can learn all about the history of the legendary wild creatures at the Museum of Chincoteague Island. Not only does this entire region have an authentic island vibe, but you can also get even more attuned with nature with a visit to the Chincoteague National Wildlife Refuge nearby.
One of the many historical attractions on the island includes the Assateague Lighthouse, which has stood since 1833 and provides exceptional views for those taking the tour. When you have worked up an appetite, the popular stop for the locals is Bill’s Prime Seafood Restaurant. It’s no-frills food that hits the spot with hearty portions.
It’s unlikely you haven’t heard the iconic slogan, “Virginia Is for Lovers,” and you are sure to love these small and charming communities considered to be the cutest of 2025. Whether it is the walkable historic districts or the genuine hospitality you can encounter, there is something for everyone. You can experience the mountain Hamlets like Floyd or the Appalachian authenticity of Abingdon, because no matter what small town in the Commonwealth you visit, it is worth the trip.
