Best Small Towns to Live in Virginia

Virginia should be at the top of your list if you’re yearning for the closeness of small-town living. The countryside brims with Instagram-worthy towns that present a unique blend of history, culture, and southern friendliness. From the tranquil island community of Chincoteague to the vibrant university town of Blacksburg, Virginia’s communities are reasons people fall in love with the state. 

Embark on a journey to explore some of the best small towns to live in Virginia. We focused on small towns with between 1,000 and 25,000 residents for this list based on recent Census figures. Any “small town” that served as a suburb of the major metro areas around Washington, DC, was excluded. Sorry Vienna and Falls Church! We also aimed to highlight small towns in different regions, from the seaside to the mountains, to showcase Virginia’s variety. 

Without further wait, here are some of the best small towns in Virginia based on their historical significance, cultural attractions, natural beauty, and overall charm:

Chincoteague

Population: 3,000

Region: Eastern Shore

Chincoteague Island is famous for its wild ponies, beautiful beaches, and abundant wildlife in the nearby Chincoteague National Wildlife Refuge. While the “top 10 island in the US” is primarily a vacation destination, the town is a quaint waterfront village with an old-timey feel with its pastel-painted buildings and salt-washed boardwalks. Because of the tourism industry, you’ll find mini-golf, horseback rides, waterfront seafood restaurants, and ice cream shops.

Locals primarily work in hospitality, fishing, or agriculture. But when they’re done for the day, the beautiful island is ready for you to enjoy. Take long walks on the beach, try surfing, or take a ferry ride to Assateague Island National Seashore! 

There’s a mixture of homes here, from historic Victorian properties to vacation waterfront condos used as seasonal homes. 

Middleburg

Population: 700

Region: Northern Virginia 

Middleburg is the perfect spot if you’re looking for a peaceful, pastoral escape. This historic town was founded in 1787 and is known as an equestrian mecca in Virginia’s horse country. Fox hunts still happen here. 

While steeplechasing and fox hunting draw the spectators, the town offers plenty of outdoor activities for nature lovers as well—hike at nearby parks like Sky Meadows or play a round at Shade Mountain. And its rolling hills are also home to some of the state’s most beautiful wineries and vineyards. 

Middleburg shines with its quaint antique shops, art galleries, and even an opera house, all housed in a downtown historic district that dates to the earlier 1800s. 

Housing options in Middleburg range from stunning Georgian-style mansions to cozy cottages on large country estates. Famous celebrities like Liz Taylor and Jackie Kennedy have built homes in the Middleburg region. 

Culpeper

Population: 20,000

Region: Central/Northern VA

Surrounded by Virginia’s wine country, Culpeper’s scenic countryside teems with horse farms and vineyards. As a town, the character is evident here from your first drive downtown. Founded in 1748, Culpepper has a deep Civil War history, with three battlefields in its vicinity. The most well-known is probably Cedar Mountain.

The small-town charm of Culpeper is alive and well. Find local organic markets, bike trails, wineries, and cidery. The locals love to throw events, from car shows to an old-fashioned Fourth of July Festival. And why not get outdoors at parks like Commonwealth Park, home to one of the state’s largest equestrian facilities. The beautiful Shenandoah National Park and Skyline Drive are just 30 minutes drive. 

Living in Culpeper is affordable—you’ll find various housing options ranging from new townhomes to historic properties. And if you like being near the action, you can commute to Washington, DC, in under an hour! 

Front Royal

Population: 15,000

Region: Shenandoah Valley

Front Royal is proud to be a country town. The Shenandoah Valley gateway town’s claim to fame is being where the legendary “Stonewall” Jackson cut off Union forces on the way to Manassas during the Civil War. 

Contemporary Front Royal has multiple attractions for those who love all four seasons. It sits at the entrance to Skyline Drive and the Shenandoah National Park; it has the Blue Ridge Mountains in its backyard. Hike, mountain bike, and camp in the misty hills. Go fly fishing and kayaking in the nearby rivers and streams. Squeeze yourself for spelunking in Luray Caverns, take a wine country tour, or ride horseback through the mountains. Or simply drive the skyway in the fall for leaf peeping.

The town matches the impressive outdoor recreation selection with a proud local culture. It has everything you’d want besides the historic driving tours and 19th-century buildings for a well-rounded life. The downtown is one part classic Main Street with brick storefronts and expansive windows, an old theater, and a central town park with a gazebo, and one part contemporary haven, with colorful murals, sculptures, craft breweries, and gastropubs. Locals have many unique shops, restaurants, and galleries to explore. The things to do include a monthly Art Walk, Minor League Baseball games, and a summer concert series.

The housing options here include historic homes and peaceful Shenandoah Valley estates. 

Lexington

Population: 7,300

Region: Blue Ridge Mountains/ Shenandoah Valley

Lexington, situated in the heart of the Shenandoah Valley, is home to Washington and Lee University and the Virginia Military Institute. Lexington takes great pride in its esteemed colleges, and rightfully so. While these universities may be smaller, they consistently rank among the finest in the state and the nation. Imagine a small-town college experience in the mountains. In this place, young people are embraced and valued as integral members of the community. 

Even though it’s clear this is an old town, from the wrought-iron fences, columned old buildings, and brick sidewalks, it has a fun energy thanks to the two colleges. It’s evident in the Rockbridge Community Festival, a long-running summer event with all the hallmarks of a Southern American festival: live music, craft vendors, and family activities. Or catch a double feature at the local Drive-In Theater, a landmark attraction still going strong. And the locals really turn out for Friday night football games at VMI! 

Downtown is a highly walkable place with historic sites, from the Lee Chapel & Museum to the Stonewall Jackson House. It has a robust selection of locally owned restaurants and breweries. Dine with seasonally-inspired menus or enjoy outdoor seating on those lovely summer days. 

Nature lovers will find plenty to explore in and around Lexington—hike, camp, or go fishing at nearby waterways like Lake Robertson. Two walking trails start at the W & L campus, and three more are within a few miles of downtown. But drive a little further, and you’ll have the Blue Ridge Mountains and all its treasures to keep you busy. Take sunset hikes, pick fresh blackberries, or hike to neat geological features like the Devil’s Marblepark or Natural Bridge. Camp on the Appalachian Trail or flyfish the Rockbridge County clear streams.

Housing options range from beautiful historic Victorians to newly built homes in the suburbs. Plus, you’re just under an hour’s drive away from Roanoke! 

Williamsburg

Population: 15,000

Region: Coastal VA/ Historic Triangle

One of America’s original colonial towns, Williamsburg is best known for its living museum at Colonial Williamsburg. Known as “the birthplace of American democracy,” the historic sites are enchanting and fascinating with their preserved buildings, museums, and reenactments that transport visitors back to the 18th century. 

[Graphic: Call out box: Colonial Williamsburg is the world’s largest living history museum, covering 301 acres.]

But there’s more to the town than its colonial past. Modern Williamsburg is a booming resort destination in Hampton Roads, thanks to the abundance of golf courses, spas, and upscale restaurants. Locals can visit theme parks like Busch Gardens for thrilling rides or Water Country USA for summer fun in the sun! No wonder it’s a top vacation destination in the US and Virginia.

People also come to learn and work for the College of William and Mary, one of the nation’s oldest and premier universities. Williamsburg may be a tourist town, but its job market is rather diverse, thanks to the college and the nearby military bases. And to accommodate all those visitors, the roads are well-kept, and public transportation makes it easy to get around.

Residents really have everything they could want in Williamsburg or the surrounding towns: excellent beaches, quality schools, access to health care, many parks, and a great cost of living. 

Abingdon

Population: 8,400

Region: Virginia Highlands 

Another small town in the Appalachian Mountains, life in Abingdon has the relaxed mountain atmosphere and those folksy arts and crafts shops, but there’s more going on here. For instance, its famous Barter Theatre is one of the oldest continuously operating theaters in the country, and The Tavern claims to be Virginia’s oldest bar.

In town, the art tradition is visible in the renovated Arts Depot, where studios and galleries have taken up residence in the remodeled train depot, an eclectic art museum in a former college building, and a long-running mountain artists collective. 

Abington also has a famous food scene, and we’re not kidding. USA Today claimed it had the best small-town food scene in the country for four years running, from 2019-2022. Locals like to say it has the most restaurants per capita, even more than New York City. Whether true or not, it does have a large number of independently owned restaurants, a farmer’s market, vineyards, and farms.

You’ll need to watch your waistline with all those great places to eat. Luckily, a thriving outdoor scene will fuel your days and burn calories. Take a shuttle and bike the 34-mile Virginia Creeper Trail from the mountaintop down through the farmlands. Go fishing at Abingdon’s nearby lakes and streams, or explore the state parks. In the winter, you can even ski at nearby resorts like Massanutten! 

Staunton

Population: 26,000

Region: Shenandoah Valley

Whether you love history, outdoor recreation, or simply appreciate small-town charm, Staunton impresses with its mix of old and new. The well-preserved architecture from various periods, including Victorian and Georgian styles, is the most distinct visual feature when you first come into town. 

Regarding attractions, American Shakespeare Center’s Blackfriars Playhouse adds to its cultural appeal. It fully replicates Shakespeare’s indoor theater. Other top draws include a living history museum and the Woodrow Wilson Presidential Library. 

The historic Main Street has no shortage of restaurants and breweries to appease your tastebuds. Stroll the brick-laid sidewalks and browse over 80 tall-windowed storefronts that feel like they’ve been replicated from an old photograph. In the warmer months, the street shuts down to cars on the weekends for the “Shop and Dine Out” days. It feels lively as Staunton supports street performers and buskers who play live music from the stoops of the old buildings. 

Staunton has its fair share of outdoor activities. There’s a municipal golf course, biking trails, and 2,000 acres of open nature preserves. Hike in the George Washington National Forest or picnic at Gypsy Hill Park. You can even go kayaking on the Shenandoah River! 

It’s incredibly convenient to get to and from, thanks to the two Interstates intersecting in the town. That’s partially why this is one of the larger small towns on our list. But its larger size also means more choices for health care, grocery shopping, education, and housing.

Live in a Virginia small town

A Virginia small town is just the ticket to adventurous but peaceful living. From colonial Williamsburg to modern Abingdon, these charming towns have more than history and scenic beauty, although that certainly adds to their charm. Find great job opportunities, quality schools, access to medical care, plenty of parks, and an affordable cost of living.

Discover these top small towns and start exploring all that makes their lifestyle desirable with a local real estate agent.