The Most Beautiful Towns in Virginia

Lexington, Virginia, is where Confederate generals Robert E Lee and Stonewall Jackson are both buried
Lexington, Virginia, is where Confederate generals Robert E Lee and "Stonewall" Jackson are both buried | © Mark Summerfield / Alamy Stock Photo
Ann Marshall-Thomas

Established as a colony of the London Company in 1607, Virginia has one of the richest histories in the United States. It’s nicknamed the Mother of Presidents, as more presidents have come from Virginia than any other state. Virginia is also geographically diverse, with a low-lying bay area, a plains region and the beautiful Blue Ridge Mountains. The best way to experience the rich history and diverse geography of Virginia is through its small towns – here are the most beautiful.

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Staunton was first settled in 1732, and the town served as the capital of Virginia in June 1781, when legislators fled from both Richmond and Charlottesville during the American Revolution. Staunton is the birthplace of president Woodrow Wilson and home to the American Shakespeare Center, the only authentic replica of the Blackfriars Theatre in the world.


A historical town whose site was established by the explorer Daniel Boone in the 1770s, Abingdon is the perfect historical setting for a quaint weekend getaway. Main Street is lined with buildings and homes that date to 1779, and the town is home to the Barter Theater, where patrons can still barter for a ticket.


The town of Chincoteague became famous by way of Marguerite Henry’s children’s book Misty of Chincoteague, which was made into a film in 1961. The story focuses on the Chincoteague wild ponies found on the neighboring Assateague Island. Today, this quaint fishing town is the perfect location from which to spot the wild ponies and experience island living.


Named after Lexington, Massachusetts, where the first shot was fired in the American Revolution, Lexington, Virginia, is home to the Virginia Military Institute, and Washington and Lee University. Confederate generals Robert E Lee and “Stonewall” Jackson are both buried here. In addition to rich historical sites and monuments, Lexington is also home to several well-known farm-to-table restaurants.


Located in the Hampton Roads region of Virginia, Smithfield is best known for curing and producing Smithfield Ham. Today, in order to be considered a Smithfield Ham, a ham must be processed within the town limits. Smithfield Foods is still the largest hog producer and pork processor in the world. In addition to delicious ham, visitors to Smithfield can enjoy the historic Victorian homes here.


Culpeper is situated less than an hour from three desirable cities: Fredericksburg, Charlottesville and Washington DC. It is easily accessible by train, with a station in the midst of the historic downtown district. Culpeper is dotted with Victorian and colonial homes, galleries, shops and restaurants.


Middleburg, Virginia, has a well-deserved reputation as the horse and hunt capital of America. The town center is listed in the National Register of Historic Districts and is home to the Red Fox Inn, the oldest building in Middleburg, dating back to 1728. Some of the wealthiest people in the world keep their horses on farms near Middleburg, and the town is dotted with high-end shops.


Originally called Port Scarborough, Onancock was founded in 1680. It is located on the Eastern Shore of Virginia and was once a frequent stop for steamboats carrying cargo to Norfolk or Baltimore. The town is surrounded by four branches of Onancock Creek, and visitors often enjoy meandering past the Victorian waterfront homes that stretch to the Chesapeake Bay.


Located in Highland County, the village of Monterey is linked to the upper Shenandoah Valley, just over the Bull Pasture and Shenandoah mountains from Staunton. Monterey is ripe for niche tourism, with beautiful country homes, old churches, nearby hiking trails and the annual Highland Maple Festival, which takes place each March.


On the shore of 78sqmi (202sqkm) Kerr Lake, Clarksville is the only lakeside town in Virginia. The town hosts several yearly festivals, including Lakefest each July and the Clarksville Wine Festival every April. The town is full of shops, restaurants and even some nightlife. The surrounding area offers attractions such as Prestwood Plantation, Three Sisters of Shiney Rock Winery and the Occoneechee State Park.

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