From tranquil lakeside communities to eclectic Appalachian arts havens, here are the 10 most charming small towns in Virginia.
While most people reside in Virginia’s large population centers, like Virginia Beach, Richmond, and Arlington, the commonwealth isn’t short on small towns that punch above their weight. In fact, these small towns attract visitors from near and far because of their charm and unique personalities.
From tranquil lakeside communities to eclectic Appalachian arts havens, here are the 10 most charming small towns in Virginia.
Northern Virginia
Despite its urban sprawl, Northern Virginia’s small towns of Middleburg and Warrenton offer a slower pace of life.
Middleburg
Known as “The Nation’s Horse and Hunt Capital,” Middleburg in Loudoun County has a population of less than 700. Despite its small size, the town has a big personality with plenty of options to keep visitors busy.
The Museum of Hounds & Hunting North America at 11 W. Washington St. should be at the top of your list. It features a wide range of foxhunting art, artifacts, and memorabilia. Open from 12 to 4 p.m. Friday through Sunday, the museum offers self-guided and docent-guided tours.
Round out your knowledge of hunt country by also visiting the National Sporting Library & Museum at 102 The Plains Rd. It spotlights the heritage of angling, horsemanship, shooting, steeplechasing, foxhunting, flat racing, polo, and coaching through exhibits and activities. Visit between 10 a.m. and 5 p.m. Wednesday through Sunday.
Stop by the Red Fox Inn & Tavern, a circa-1728 historic fieldstone inn and tavern, for dinner before heading to Salamander Middleburg, a resort situated on 340 acres, for the night. Head to the Gold Cup Wine Bar for a nightcap.
Warrenton
The county seat of Fauquier County, Warrenton is less than 50 miles outside of Washington, D.C. and has a population of just over 10,000. It’s known as being “the star of the Piedmont,” with the Blue Ridge Mountains scattered along the surrounding area.
Upon arrival in the town, stop by the Warrenton-Fauquier Visitor Center at 21 Main St. From there, wander around Old Town Warrenton to explore the shopping and dining options. Try some Southern fare in an 18th-century train station at Claire’s At The Depot and browse work from local artists at Berkley Gallery.
In the afternoon, head to the family-owned and operated Molon Lave Vineyards at 10075 Lees Mill Rd. to try one of the four 2026 Virginia Governor’s Cup award-winning wines, including the 2024 Petit Manseng.
Plan to stay overnight at the Airlie Hotel, a sophisticated historic hotel set against the backdrop of 300 acres of farmland and rolling hills. Take an afternoon stroll along the banks of Lake Stanley, which is open for fishing. Enjoy dinner at Harry’s Tavern, a farm-to-table restaurant that sources ingredients from Airlie’s Berkshire Farm.
History buffs should check out The Cold War Museum, which tells the story of the war through interpretive displays. The museum is located on a former Army signals listening station, so be sure to check out the collection of radios and cryptographic equipment. It’s open from 11 a.m. to 4 p.m. on Saturdays and 1 to 4 p.m. on Sundays.
Central Virginia
Skip Richmond and give the small yet active Central Virginia towns of Orange and Ashland a try.
Orange
Go to Orange, a town of 4,800 in Orange County, to get lost in rolling hills and the views of the surrounding Blue Ridge Mountains.
Learn more about Orange County’s most famous resident—James Madison at the James Madison Museum at 129 Caroline St. The museum features furniture and personal items belonging to the fourth president of the United States. It’s open from 10 a.m. to 4 p.m. Monday through Saturday.
Afterward, stop by Spoon & Spindle at 323 North Madison Rd. in the Historic Silk Mill for a seasonal brunch. You can’t go wrong with the crab cake benny.
Ashland
Only 16 miles north of Richmond, Ashland, a town of 7,000 in Hanover County, gives you the type of small-town charm you just can’t find in a big city.
The best way to experience the town is to explore the downtown, where you’ll want to check out the “Secretariat Racing Into History” statue. The bronze figure stands at 1.5 times life-size, depicting Secretariat and his jockey in a racing stride. It’s in the plaza across from the Ashland/Hanover Visitor Center at 112 North Railroad Ave.
You’ll also find the Ashland Theatre, a historic venue that serves as the cultural hub of the town, at 205 England St. It offers musical performances, first-run and classic film screenings, and guest speakers.
Pop into Ash & Olive, an elevated Euro-American fine-dining restaurant, at 107 S Railroad Ave. for a meal. Give the prosciutto and arugula pizza a try.
Coastal Virginia
While Virginia Beach is a solid vacation destination, the crowds can be a bit tiring, so go to Smithfield and Kilmarnock in Coastal Virginia instead.
Smithfield
While Smithfield, a town of 8,500 in Isle of Wight County, is a pleasant place to visit, it’s an especially appealing destination for those who love ham, bacon, and really any kind of pork product because of the town’s legacy stemming from the Smithfield ham law from the 1920s.
Explore the town’s ham legacy by visiting the Isle of Wight County Museum at 103 Main St., where you’ll find the world’s oldest ham, as well as the world’s oldest peanut. The museum is open from 10 a.m. to 4 p.m. Monday through Saturday and 12 to 4 p.m. on Sunday.
From there, you can follow the Porcine Parade, a collection of eight life-size market hog statues spread throughout the Main Street area.
Finish up your tour of the town with a downhome southern meal at Taste of Smithfield at 217 Main St. You can’t go wrong with the country ham biscuits.
Kilmarnock
Kilmarnock is a quiet Northern Neck town of 1,400 in Lancaster and Northumberland counties that serves as a gateway to the Rappahannock River.
The best way to get a feel for the town is to stroll through the Steptoe’s District, the downtown area where you’ll find plenty of local shops to browse, where owners love having conversations with out-of-town visitors.
A visit to the town wouldn’t be complete without a stop at the Kilmarnock Antique Gallery, a 22,000-square-foot shopping experience. It’s the home of the “Oyster Plate Lady.” A one-of-a-kind oyster plate is the perfect souvenir to take home with you.
Be sure to grab a meal at Lee’s Restaurant, a town mainstay for more than 80 years. You can’t go wrong with the oysters and a slice of homemade pie.
Western Virginia
Take in history and culture in the Western Virginia towns of Floyd and Lexington.
Wytheville
Wytheville, the seat of Wythe County, has around 8,000 residents. It’s perhaps best known as the birthplace of Edith Bolling Wilson, the first lady during Woodrow Wilson’s presidency.
The town has done a great job of preserving Wilson’s legacy with the Edith Bolling Wilson Birthplace Museum, which chronicles her life from Wytheville to the White House through various exhibits and programs. Be sure to check out the “Edith in Context: Socio-Economic Conditions at the Turn of the Twentieth Century” exhibit. The museum is open from 10 a.m. to 4 p.m. Tuesday through Saturday at 145 E. Main St.
While in the downtown, be sure to go on the Historic Walking Tour, which tells the story of the town’s founding in the late 18th century, its role in the Civil War, and the changes the town has undergone in modern times.
You’d also be remiss if you didn’t take in a show at the Wohlfahrt Haus Dinner Theatre at 170 Malin Dr. You’ll get a four-course meal while watching a classic musical, like “Footloose,” which runs from Sept. 11 through Oct. 25.
Floyd
Floyd, a town of less than 400 in Floyd County, has developed a reputation for being an eccentric off-the-beaten-path destination for arts and culture.
The Floyd County Store at 206 S. Locust St. is one of the primary draws, serving as an incubator for old-time music and dancing. The Friday Night Jamboree is held every Friday. It features an hour of gospel music, then two hours of dance bands. Sundays are devoted to Americana Afternoons. Be sure to also stop by The Soda Fountain at The Floyd Country Store for an IDA red ice cream soda.
The Floyd Center for the Arts is equally worth a visit to check out some of the unique creativity and craftsmanship that makes Appalachia so special. It’s located in an old barn and silo at 220 Parkway Lane S.
Be sure to also stop by 823 E Main St. for a cup of coffee from Red Rooster, a local roaster and coffee house.
Southern Virginia
Hidden along the North Carolina border, explore small Southern Virginia: the lake and river towns of Clarksville and South Boston.
Clarksville
Clarksville in Mecklenburg County, a town with around 1,300 residents, is defined by its status as being Virginia’s only lakeside town. It sits against the 50,000-acre Buggs Island Lake, making it ideal for outdoor fun.
The best way to experience the lake is to visit Occoneechee State Park, which offers 20 miles of trails and plenty of docks for fishing, boating, and swimming. Visit the park at 1192 Occoneechee Park Rd.
If visiting Clarksville for a romantic getaway, consider staying at Cooper’s Landing Inn & Traveler’s Tavern, a circa-1830 charming place to stay after a fun day on the water. The tavern, which is located at 801 Virginia Ave., offers farm-to-table dining on a trellised patio along with a wine bar.
South Boston
Located in Halifax County, South Boston, a town with a population of nearly 8,000, borders the Dan River. Stop by the Halifax County/South Boston Visitor Center at 1180 Bill Tuck Hwy.
Be sure to check out Downtown South Boston for shopping, dining, and entertainment.
Try the Holler, a spinach wrap that comes with turkey, Swiss cheese, Duke’s mayonnaise, cranberry orange relish, and spring mix, at Southern Plenty at 206 Main St.
Grab a new pair of shoes at McCollum-Ferrell Shoes, a South Boston mainstay since 1947, at 409 Main St.
And visit the town in February to watch the annual Crossing of the Dan, a commemoration of Gen. Nathanael Greene guiding the Continental Army’s retreat across the Dan River on Feb. 14, 1781, to avoid Gen. Charles Cornwallis.
