8 Virginia Small Towns That Keep Showing Up on Travel Lists

Virginia’s charming small towns have become favorite destinations for travelers seeking authentic experiences away from crowded cities.

These picturesque communities offer historic architecture, stunning natural scenery, unique shops, and welcoming locals that make visitors feel right at home.

From mountain retreats to waterfront villages, these eight towns continue earning spots on national travel lists year after year.

1. Abingdon

Nestled in the scenic Appalachian Mountains of Southwest Virginia, Abingdon has earned recognition as one of the most culturally rich small towns in America.

The town’s crown jewel is the Barter Theatre, Virginia’s official state theatre, which began during the Great Depression when actors accepted food as payment for performances.

Today, this professional theatre at 127 West Main Street continues to produce world-class shows that draw audiences from across the region.

Walking down Main Street feels like stepping back in time, with beautifully preserved 19th-century buildings housing art galleries, boutiques, and restaurants.

The 34-mile Virginia Creeper Trail starts just outside town, offering cyclists and hikers a stunning journey through forests, over trestles, and past old railroad stations.

Families love visiting during summer when the town hosts concerts and festivals in the streets.

Food lovers appreciate the farm-to-table restaurants that showcase regional ingredients and traditional Appalachian recipes with modern twists.

The Martha Washington Inn & Spa, a historic hotel dating to 1832, provides luxury accommodations in an elegant setting that once served as a college and Civil War hospital.

Art enthusiasts find inspiration at the William King Museum of Art and the numerous galleries featuring local and regional artists.

Antique shops line the streets, offering treasures from different eras that tell stories of the region’s past.

The town’s commitment to preserving its heritage while embracing creativity makes it a destination that appeals to history buffs and modern travelers alike.

Whether you’re catching a show, biking the trail, or simply enjoying the mountain views, Abingdon delivers an unforgettable small-town experience.

2. Middleburg

Known as the nation’s horse and hunt capital, Middleburg exudes elegance and old-world charm in Virginia’s scenic Loudoun County.

This wealthy enclave has attracted presidents, celebrities, and equestrian enthusiasts for generations with its refined atmosphere and stunning countryside.

Washington Street, the main thoroughfare, features high-end boutiques, antique stores, and gourmet restaurants housed in historic buildings that date back to the 1700s.

The Red Fox Inn & Tavern at 2 East Washington Street, established in 1728, stands as one of America’s oldest continuously operating inns and serves exceptional cuisine in a cozy colonial setting.

Horse farms with pristine white fences stretch across the rolling hills surrounding town, creating postcard-perfect views in every direction.

Visitors can explore the National Sporting Library & Museum, which houses the finest collection of horse and field sport literature and art in America.

Wine enthusiasts enjoy touring nearby vineyards that produce award-winning wines while offering breathtaking views of the Blue Ridge Mountains.

The Christmas in Middleburg celebration transforms the town into a winter wonderland each December with carolers, horse-drawn carriage rides, and festive decorations.

Shopping here means discovering unique treasures, from custom leather goods to fine jewelry and designer clothing.

The Middleburg Film Festival attracts cinema lovers each October, screening independent films and hosting discussions with filmmakers.

Despite its sophistication, the town maintains a welcoming small-town feel where shopkeepers know regular customers by name.

Photographers find endless inspiration in the pastoral landscapes, historic architecture, and magnificent horses that define this special place.

3. Cape Charles

Sitting on a peninsula where the Chesapeake Bay meets the Atlantic Ocean, Cape Charles offers a relaxed beach town vibe without the crowds of larger coastal destinations.

This hidden gem on Virginia’s Eastern Shore has experienced a renaissance in recent years while maintaining its authentic small-town character.

The mile-long public beach features soft sand and gentle waves perfect for families with young children who want to play safely in the water.

Victorian and Colonial Revival homes line the tree-shaded streets of the historic district, many beautifully restored and painted in cheerful colors.

Mason Avenue, the main street, buzzes with activity as visitors browse shops selling coastal decor, artwork, and locally made crafts.

The Cape Charles Brewing Company at 2198 Stone Road serves craft beers brewed on-site, along with delicious food in a casual atmosphere where locals and tourists mingle.

Kayakers and paddleboarders explore the calm bay waters, often spotting dolphins, herons, and other wildlife along the shoreline.

The fishing pier extends far into the bay, providing excellent opportunities to catch flounder, croaker, and other species.

Sunset watching becomes a nightly ritual here, with spectacular shows of orange, pink, and purple painting the western sky.

The nearby Cape Charles Natural Area Preserve protects rare coastal habitats where nature lovers can hike trails and observe migrating birds.

Bed and breakfasts in restored historic homes offer comfortable accommodations with personalized service and homemade breakfasts.

The town’s compact size makes it easy to explore on foot or bicycle, creating a vacation pace that truly feels relaxing and rejuvenating.

4. Staunton

Pronounced “STAN-ton” by locals, this Shenandoah Valley gem combines rich history, vibrant arts culture, and mountain beauty in one walkable downtown.

The birthplace of President Woodrow Wilson, Staunton has transformed its historic buildings into thriving spaces for theatre, dining, and shopping.

The American Shakespeare Center operates the Blackfriars Playhouse at 10 South Market Street, a recreation of Shakespeare’s original indoor theatre where actors perform by natural light and candlelight.

Beverley Street, the main commercial corridor, showcases beautifully restored Victorian storefronts filled with independent bookstores, galleries, and restaurants.

The Stonewall Jackson Hotel, built in 1924, anchors downtown with its elegant lobby and rooftop dining that offers panoramic views of the surrounding mountains.

Foodies rave about the farm-to-table restaurants that highlight ingredients from nearby farms and producers in the fertile valley.

The historic Wharf District along the railroad tracks has evolved into a trendy area with breweries, live music venues, and creative eateries.

Families enjoy the Frontier Culture Museum, an outdoor living history site where interpreters demonstrate daily life in early American, English, German, and Irish farmsteads.

The surrounding Shenandoah Valley provides endless opportunities for hiking, with Skyline Drive and numerous trails just minutes from downtown.

Mary Baldwin University adds youthful energy to the town, with students contributing to the artistic and cultural vitality.

Antique lovers spend hours exploring multi-dealer shops packed with furniture, collectibles, and vintage treasures from different eras.

The combination of mountain scenery, performing arts, history, and culinary excellence explains why Staunton consistently appears on lists of America’s best small towns.

5. Occoquan

This tiny waterfront village along the Occoquan River packs more than 100 shops, galleries, and restaurants into just a few blocks of historic charm.

Located in Northern Virginia about 30 miles from Washington D.C., Occoquan serves as a popular day trip destination for those seeking small-town character close to the city.

Mill Street, the main shopping area, winds along the river with brick sidewalks connecting stores housed in restored 18th and 19th-century buildings.

Visitors discover everything from handmade jewelry and pottery to antiques, home decor, and specialty foods as they stroll from shop to shop.

The Artists’ Undertaking Gallery at 309 Mill Street showcases works by local artists, including paintings, sculptures, photography, and fiber arts.

Restaurants offer waterfront dining where patrons can watch boats pass by while enjoying fresh seafood, Italian cuisine, or classic American fare.

The Occoquan Regional Park provides hiking trails, picnic areas, and boat launches for those wanting to explore the natural beauty surrounding the village.

Special events throughout the year, including craft shows and holiday celebrations, draw crowds who appreciate the festive small-town atmosphere.

The Occoquan River provides a scenic backdrop for the village, with its calm waters reflecting the historic buildings and creating perfect photo opportunities.

Many shops occupy spaces that once served as mills, warehouses, and other industrial buildings from when the town was a bustling port.

The compact layout makes it easy to explore everything on foot in an afternoon, though many visitors find themselves lingering longer than planned.

This combination of history, shopping, dining, and riverside beauty creates an experience that feels both nostalgic and refreshingly different from typical suburban shopping centers.

6. Lexington

Home to two prestigious colleges and steeped in Civil War history, Lexington combines academic energy with southern charm in the beautiful Shenandoah Valley.

Washington and Lee University and Virginia Military Institute shape the character of this town, bringing intellectual vitality and a youthful population to historic streets.

The stunning campus of Washington and Lee, with its white-columned buildings and manicured lawns, invites visitors to stroll through grounds where Robert E. Lee served as president after the Civil War.

Downtown Lexington features independently owned shops, bookstores, and restaurants clustered around the historic courthouse square.

History enthusiasts visit the Lee Chapel and Museum on the Washington and Lee campus to see the recumbent statue of Lee and learn about his post-war years.

The VMI Museum at 415 Letcher Avenue tells the story of the nation’s oldest state-supported military college and its famous alumni.

Stonewall Jackson’s home at 8 East Washington Street offers tours that provide insight into the Confederate general’s life before the war.

The nearby Natural Bridge, a 215-foot limestone arch, served as a sacred site for Native Americans and later attracted visitors including Thomas Jefferson, who once owned it.

Main Street restaurants range from casual cafes to upscale dining, many featuring locally sourced ingredients and regional specialties.

The surrounding mountains offer hiking, including trails to waterfalls and overlooks that provide breathtaking valley views.

The Lime Kiln Theater presents outdoor performances during summer months in a unique setting among historic lime kilns.

This blend of education, history, mountain beauty, and small-town hospitality creates a destination that appeals to diverse interests and keeps appearing on travel recommendation lists.

7. Smithfield

Famous for its heritage of ham production, Smithfield offers much more than culinary history along the scenic banks of the James River.

This charming Isle of Wight County town features one of the largest collections of historically significant buildings in Virginia, with more than 60 structures predating the Civil War.

Main Street showcases beautifully preserved colonial, Federal, and Victorian architecture housing boutiques, antique shops, and local restaurants.

The Smithfield and Isle of Wight Convention & Visitors Bureau at 335 Main Street occupies a historic building and provides information about the town’s attractions and history.

St. Luke’s Church, built in 1632, stands as the nation’s oldest existing church of English foundation and features original Gothic architecture with buttresses and tracery windows.

The Windsor Castle Park along the riverfront provides walking paths, picnic areas, and boat launches where residents and visitors enjoy water activities.

Smithfield Station, a waterfront hotel and restaurant complex, offers marina facilities and dining with river views where boaters can dock and explore the town.

The Isle of Wight Museum at 103 Main Street displays artifacts and exhibits that tell the story of the region from Native American times through the present.

Annual events like the Smithfield Wine and Brew Fest bring together local wineries, breweries, and food vendors for celebrations along the waterfront.

The town’s compact historic district makes it perfect for walking tours where visitors can admire architectural details and learn about buildings that have stood for centuries.

Local restaurants serve the famous Smithfield ham, a delicacy that must be produced in town according to specific curing methods to earn the name.

The peaceful riverside setting combined with rich history and preserved architecture explains why this town continues attracting travelers seeking authentic Virginia experiences.

8. Monterey

Perched high in the Allegheny Mountains, Monterey serves as the county seat of Highland County, Virginia’s least populated and most rural county.

This mountain village sits at 3,000 feet elevation, earning Highland County the nickname “Virginia’s Switzerland” for its cool climate and alpine scenery.

Main Street features a collection of local shops, the historic Highland Inn built in 1904, and the stately courthouse that anchors the small downtown.

The surrounding landscape consists of working farms, forests, and mountains that create some of the most beautiful pastoral scenes in Virginia.

The Highland Maple Museum celebrates the county’s maple syrup industry, which thrives in the cool mountain climate perfect for sugar maples.

Each March, the Highland Maple Festival draws thousands of visitors who come to taste maple products, enjoy mountain music, and experience rural mountain culture.

Outdoor enthusiasts find endless opportunities for hiking, fishing, and wildlife watching in the surrounding George Washington National Forest.

The Laurel Fork area offers particularly stunning hiking through old-growth forests along pristine mountain streams.

Local restaurants serve hearty mountain fare, including trout from nearby streams and lamb from Highland County farms.

The Highland Center at 68 West Main Street provides visitor information and showcases local crafts and products made by county residents.

Photographers travel from far away to capture the misty mountain mornings, rolling farmland, and changing seasons that paint the landscape in dramatic colors.

The isolation and natural beauty that define Monterey create a retreat-like atmosphere where visitors can truly disconnect from busy modern life and experience the pace of rural mountain living.