10 Coolest Towns in Virginia for a Summer Vacation

The Chincoteague wild pony swim across the Assateague channel runs every last Wednesday of July, driven by a volunteer "Saltwater Cowboys" crew that has herded the same wild herd between islands since 1925. Staunton runs the only year-round Shakespeare repertory company in the United States that performs inside a faithful reproduction of the 1599 Blackfriars Playhouse. Luray Caverns runs the world's only Great Stalacpipe Organ, a 3.5-acre lithophone played by tapping stalactites with rubber mallets. The ten Virginia towns below each hold one specific summer-anchored draw worth the drive.

Chincoteague

Chincoteague is a small Eastern Shore island town (population about 2,800) just inside the Assateague barrier island. The Chincoteague Pony Swim, held the last Wednesday of July since 1925, drives the wild pony herd across the narrow channel between Assateague and Chincoteague at slack tide. The Saltwater Cowboys, a volunteer crew organized by the Chincoteague Volunteer Fire Company, manages the herd year-round. Foals are auctioned the following day to keep the herd at sustainable size (about 150 animals) and to fund the fire company's operations.

Outside the pony week, the Chincoteague National Wildlife Refuge covers most of the southern end of Assateague Island with 14,000 acres of beach, dunes, salt marsh, and pine forest. The 1867 Assateague Lighthouse, a red-and-white candy-striped 142-foot tower, is climbable in summer for views over the refuge. Daisey's Island Cruises runs daily wildlife tours that look for the wild herd in their natural marsh habitat.

Smithfield

Smithfield is the small Isle of Wight County town (population about 8,500) that gave its name to Smithfield Ham, the dry-cured country ham aged a minimum of six months that has been federally protected since 1968 (the Code of Virginia restricts the "Smithfield Ham" label to hams cured within the town limits). Smithfield Foods, headquartered here, remains the largest pork producer in the world. The Isle of Wight County Museum on Main Street runs ham-curing history exhibits and a one-room schoolhouse alongside the Powhatan archaeological collection.

St. Luke's Historic Church, four miles north of town, is the oldest existing church of English foundation in the United States, with construction beginning around 1632 and stained glass dating to the 1660s. The annual Smithfield Olden Days Festival each early June celebrates the town's colonial heritage with reenactments and craft demonstrations. Bacon Brothers Public House and the Smithfield Inn handle the food scene with menus heavy on the namesake ham.

Luray

Luray (population about 5,000) is the Shenandoah Valley town that contains the entrance to Luray Caverns, the largest cave system in the eastern United States and a US National Natural Landmark since 1974. The cavern's signature feature is the Great Stalacpipe Organ, a 3.5-acre electromechanical lithophone invented by Pentagon scientist Leland Sprinkle in 1956 that taps stalactites with rubber mallets to produce notes. It is the world's largest musical instrument by area and the only such instrument that uses naturally occurring rock formations.

Outside the cavern, Luray sits at the gateway to the Shenandoah National Park's central section, with the Thornton Gap entrance just east of town giving access to Skyline Drive. The Luray Singing Tower carillon, 117 feet tall and built in 1937, plays free public concerts on summer Sundays and Tuesdays. The Luray-Hawksbill Greenway, a 2-mile paved trail along Hawksbill Creek, threads downtown.

Clifton Forge

Clifton Forge (population about 3,500) is the Alleghany County town that served as the major Chesapeake and Ohio Railway switching yard from the 1850s through the mid-20th century. The C&O Railway Heritage Center on Ridgeway Street holds the largest collection of C&O memorabilia anywhere, including Hudson-type steam locomotive No. 614 and the only surviving C&O business car (J. P. Pevler's private car).

Douthat State Park, 12 minutes north of town, covers 4,500 acres of the Alleghany Mountains with a 50-acre lake, 40 miles of trails, and the historic Civilian Conservation Corps stone-and-timber lodge. The park was named a National Historic Landmark in 1985 for its CCC architecture. The Alleghany Highlands Arts and Crafts Center on Main Street rotates exhibitions and runs the regional juried art shows each summer.

Norton

Norton is the smallest independent city in Virginia, with a population of about 3,500 in the far southwest corner of the state. The town sits at 2,144 feet elevation in Wise County, with High Knob Recreation Area at 4,225 feet just outside city limits. The High Knob observation tower offers views across five states on clear days (Virginia, West Virginia, Kentucky, Tennessee, and North Carolina), the only point in the eastern United States with that range of sightlines.

Flag Rock Recreational Area on the south side of town covers a sandstone bluff with picnic shelters and the legendary Woodbooger trail (Norton officially declared itself a Bigfoot sanctuary in 2011). The Mountain Heritage Festival each October draws regional Appalachian music acts. Day-trippers can drive 30 minutes north to Breaks Interstate Park (the "Grand Canyon of the South") on the Kentucky border.

Cape Charles

Cape Charles (population about 1,200) sits at the southern tip of the Eastern Shore, where the Chesapeake Bay Bridge-Tunnel makes landfall after a 17.6-mile crossing from Virginia Beach. The town was founded in 1884 as the southern terminus of the New York, Philadelphia & Norfolk Railroad and laid out on a strict 644-block grid that gives the downtown its unusual right-angle character.

The Cape Charles Beach is one of the few public-access bay-facing beaches in Virginia, with calm Chesapeake water and warm summer temperatures. Kiptopeke State Park (4 miles south) covers a former World War II ferry landing with five miles of biking and hiking trails. The Cape Charles Crab and Wine Festival in mid-September is the town's signature summer-tail event, with regional seafood and Virginia wines paired across a single weekend.

Manassas

Manassas (population about 42,000) is best known as the site of the first major Civil War land battle, the First Battle of Manassas (called First Bull Run by the Union) on July 21, 1861, just three months after the war began. Manassas National Battlefield Park preserves both First Manassas and the August 1862 Second Battle of Manassas across 5,000 acres with self-guided driving tour routes.

The Manassas Museum runs Civil War interpretation alongside post-war railroad history (Manassas was a major railroad junction). The Liberia House Historic Site preserves an 1825 plantation home that Confederate General P.G.T. Beauregard used as his headquarters before First Manassas. The Hylton Performing Arts Center at George Mason University's Manassas campus hosts the Manassas Symphony Orchestra and touring acts year-round.

Ashland

Ashland (population about 7,500) sits 15 miles north of Richmond and runs its identity around two things: the Center of the Universe (an unofficial designation the town adopted in 1980 with handmade road signs), and the working CSX rail line that runs straight down the middle of England Street through downtown. Center of the Universe Brewing on North Center Street pours pints right alongside the train tracks, and the Ashland Coffee & Tea on the same strip handles the morning rush as trains rumble past every 20 minutes.

The Ashland Strawberry Faire each first Saturday in June draws around 30,000 visitors to the small downtown for a one-day strawberry-picking and craft-fair event that has run since 1987. Randolph-Macon College, founded in 1830, anchors the small-college calendar with a tree-lined Federal-era campus. The Hanover Tavern, 7 miles north in Hanover Courthouse, was established in 1733 and is among the oldest continuously operating taverns in the United States.

Abingdon

Abingdon (population about 8,200) is the Washington County town that anchors far southwestern Virginia's Appalachian arts scene. The Barter Theatre, founded in 1933 during the Great Depression when audiences paid for tickets with ham and produce, is the State Theatre of Virginia and runs a year-round professional theater season across two stages. Notable alumni include Gregory Peck, Patricia Neal, Ned Beatty, and Larry Linville.

The 34.3-mile Virginia Creeper Trail, a rail-trail that follows the former Norfolk and Western "Virginia Creeper" line from Abingdon east through Damascus to Whitetop Station, draws cyclists who can rent bikes in town, get shuttled to the high end, and coast back down the gentle railroad grade. The William King Museum of Art handles regional visual arts in the 1913 William King High School building. The Heartwood: Southwest Virginia's Artisan Gateway showcases regional craft and Appalachian heritage.

Staunton

Staunton (pronounced STAN-ton, population about 26,000) is the Shenandoah Valley city that holds the Blackfriars Playhouse, the only faithful indoor reproduction of Shakespeare's 1599 Blackfriars Theatre anywhere in the world. The American Shakespeare Center runs a year-round professional repertory season there, with universal lighting (the house lights stay on so the actors can see the audience, the original 1599 staging convention) and original-practices casting. The company is one of the few in the US that performs the full Shakespeare canon on a rolling schedule.

The Woodrow Wilson Presidential Library & Museum sits on the Coalter Street block where the 28th president was born in 1856. The Frontier Culture Museum on the south side of town runs working living-history farms representing the 17th-century West African, English, Irish, German, and American settler cultures that built the Shenandoah Valley. The Stonewall Jackson Hotel, opened in 1924, anchors downtown with a year-round live music calendar.

Ten Anchors, Ten Summers

Each of the ten Virginia towns above leads with one specific summer-anchored draw. Chincoteague's last-Wednesday-of-July pony swim. Smithfield's federally-protected ham. Luray's Great Stalacpipe Organ. Clifton Forge's CCC-built Douthat State Park. Norton's five-state sightlines from High Knob. Cape Charles's bay-facing public beach. Manassas's Civil War battlefield. Ashland's Center of the Universe trackside breweries. Abingdon's Barter Theatre and 34-mile Creeper Trail. Staunton's Blackfriars Playhouse reproduction. Pick the anchor that fits the trip.