7 Prettiest Small Towns In Virginia For A Weekend Escape

Some of Virginia's small towns sit on the tight river bends of the Shenandoah; others run along the working harbor piers of the Eastern Shore where Bay watermen still unload at the docks. The seven below stretch from the Blue Ridge across the Piedmont and out to the Chesapeake Bay, with each one built around a walkable historic core and the scenery to back up its reputation.

Woodstock

The seat of Shenandoah County, Woodstock sits along the North Fork of the Shenandoah River, with Shenandoah National Park rising to the east. Established by charter in 1761, with George Washington sponsoring the bill in Virginia's House of Burgesses, the town was one of the first to be founded west of the Blue Ridge. The Woodstock Historic District covers several centuries of buildings, including Lantz Hall and the county courthouse. North Mountain Vineyard and Winery is the local stop for regional reds and whites, and Seven Bends State Park, named for the river's tight loops just east of town, opens up swimming, hiking, and biking along the water.

Williamsburg

Williamsburg sits in the Tidewater between the James and York rivers and runs as the working core of Colonial Williamsburg, the open-air living history museum that occupies most of its original 18th-century footprint. Costumed interpreters work the trade shops along Duke of Gloucester Street, the Capitol and Governor's Palace anchor either end of the main strip, and brick taverns from the 1700s still serve dinner. Beyond the historic district, the campus of the College of William and Mary, founded in 1693 and the second-oldest college in the United States, runs into a walkable downtown of bookstores and cafes. Bassett Hall and the Williamsburg Inn add architectural weight at the edges of town.

Leesburg

Established by Act of Assembly in 1758 and named for Thomas Lee, an early colonial leader of the Lee family, Leesburg sits at the base of the eastern Blue Ridge near the Potomac River, a short drive from Washington DC. The Leesburg Historic District is on the National Register of Historic Places, with the Loudoun County Courthouse and the Paxton estate as its anchors. Just outside town, Oatlands Plantation and Morven Park add 18th- and 19th-century architecture on substantial grounds. Annual events like the Classic Car Show and the Leesburg Flower and Garden Festival fill the streets with vendors through the warm months.

Middleburg

With fewer than a thousand residents, Middleburg calls itself the "Nation's Horse and Hunt Capital" thanks to its long history of foxhunting, large estate lands, and steeplechase racing. Founded in 1787 by Revolutionary War officer Leven Powell, the Middleburg Historic District is on the National Register of Historic Places. The Red Fox Inn and Tavern, which traces its origins to 1728 as Chinn's Ordinary, is billed as the oldest continually operated inn in the country and still serves dinner. Stone walls and white-board fencing run along the surrounding pastures, with antique shops, art galleries, and tasting rooms filling the main strip in town.

Chincoteague

Chincoteague is a working island town on Virginia's Eastern Shore, connected to Assateague Island and its national wildlife refuge by a short bridge. The wild ponies that graze the marshes are the town's signature, with the annual Pony Swim across the channel each July. Main Street runs along the harbor with seafood shacks, oyster bars, and small bookshops, and the Assateague Lighthouse, a red-and-white candy-stripe tower, sits above the dunes a few miles east. Kayakers paddle the salt marshes; cyclists ride the wildlife loop.

Cape Charles

With around 1,200 residents, Cape Charles was founded in 1884 as a planned railroad and ferry town near the mouth of the Chesapeake Bay on Virginia's Eastern Shore. The downtown is a grid of late-19th-century buildings, cottages, and harbor warehouses, much of it from the original railroad-era plat. The Cape Charles Museum, set in a former power plant, traces the town's rail and ferry history. The town beach faces directly onto the Bay for warm-water swimming, and a public golf course runs along the water at the south end of town.

Onancock

Founded in 1680, Onancock is one of the oldest towns on Virginia's Eastern Shore, set at the head of Onancock Creek where the harbor still operates as a working watermen's port. The Onancock Historic District holds more than two hundred contributing buildings spanning Federal through Late Victorian architecture, and Ker Place, an 1799 Federal-style mansion, is open as a house museum. From the town wharf, a seasonal ferry runs across the Bay to Tangier Island, the soft-spoken crab-fishing community that still speaks a distinctive English dialect.

Where Virginia Slows Down

Across these seven towns, Virginia spreads out in a long arc from the Shenandoah Valley through the Piedmont and out to the Bay. River towns like Woodstock and Onancock work because of the water that runs through them; horse country towns like Middleburg and Leesburg sit on the rolling Piedmont; and Chincoteague and Cape Charles trade in the saltier rhythms of the Eastern Shore. None of them are big, but each carries the kind of detail that rewards a slower drive in.