7 Playfully Peculiar Towns In Virginia
Established as the colony of Virginia in 1624, it entered statehood as the union's tenth state on June 25, 1788. From the Chesapeake and an open portion of the Atlantic to the Appalachian Mountains, Virginia's small towns continue to inspire travelers along the coast, the river valleys, and the foothills.
The historic state feels one with the cozy falltime vibes. Whether you're an adventurer along the Appalachian/Creeper Trail, taking a breather in Damascus, or exploring the underground caverns downtown in Luray, each makes for a warm gesture to invite the colder season and warming discoveries into your heart.
Chincoteague
The wild ponies at Chincoteague National Wildlife Refuge are accessible via Beach Blvd/Rd on the eponymous island. Stick around since this peculiar town offers attention-grabbing landmarks besides Assateague's pristine beaches. Take the downtown Nature Trail by foot or bike downtown, or take a relaxing cruise for a different perspective. From the local library in an old barber shop to shops, live art, and events, how about a taste of the refuge's seafood and oyster industries?
You can drop by the Museum of Chincoteague Island and drive right through the protected marsh and forest to Assateague Island, which is popular for its beaches and graceful beauty. Or, pick a trail to stretch your legs and ascend the historic striped 142-foot Assateague Lighthouse for top views. The biannual Pony Swim draws thousands for a weekend in late September and in late July, when cowboys round up and swim the ponies across the channel for the local auction.
Clarksville
“Virginia's Only Lakeside Town” gleans popularity year-round for its relaxed waterfront setting along the western shore of the Roanoke River, where, for a heartbeat, it turns into John H. Kerr Reservoir. Aka, Buggs Island Lake, it invites an array of fun aquatic opportunities, ideal for a summer escape near the southern border. In addition to boating and paddleboarding, Clarksville stakes claim to Occoneechee State Park, a 2,600-acre outdoor playground, across the shore.
Travelers can score a campsite, fish from the shore, and explore the trails for hiking and horseback riding, plus nearby landmarks. Minutes away, Prestwould Plantation reveals the 1700s lifestyle with scenic grounds and original architecture. After all, it wouldn't be Virginia without some history and love for wine. After a stop by the Clarksville Regional Museum, travelers can look forward to a relaxing evening with several wineries and vineyards within a 10-minute radius.
Damascus
This Syrian capital namesake near the Tennessee border is wistfully known as the Trail Town USA for its connection to the Virginia Creeper Trail and the annual Massanutten Trail Race, a late spring ultra-demanding 100-mile course over the rocky terrain of Shenandoah's Massanutten Mountains. Local campgrounds are ideal for the summer, while Damascus Old Mill Inn inspires a fairytale stay on Laurel Creek for a stylish option in a stately building with grand dam views out the front door.
Recently hit by a hurricane, the 34-mile Creeper Trail remains in demand, offering scenery throughout, from rivers and bridges to wildlife, and behold, some rough but still accessible areas on bike; hence, the town's sought-after Bike Station Bike Rental & Shuttle Damascus. In addition to Appalachian Trail access at US 58, travelers enjoy local parks along two creeks, then all gather at an old-school diner or the Damascus Brewery, serving local craft on tap, sours, and ciders.
Goochland
Named after a colonist and the state's Royal Lieutenant Governor from 1727 to 1749, the quirky name draws travelers to discover more than meets the eye, some 20 minutes up the James River from the capital. Don't miss Thomas Jefferson's boyhood home as you exit Richmond. Goochland nurtures your soul with nature, unique history, and delicious eats along the outer riverbend. North River Outdoors is a sought-after local business that helps you gear up and let your spirit soar to the tune of nature.
Adventures await along the inner riverbend at the 1,565-acre Powhatan State Park, with a canoe-in campground and trails. Easy river access opens the door to tubing and canoeing, plus picnics and strolls. In addition to the town's inexpensive and delicious Bella Sicilia Italian Restaurant, take a quick drive up to the Goochland Drive-In Theatre, one of Virginia's last remaining outdoor theaters. It is open from late March through early fall, offering cozy fire pits, snacks, and a playground.
Luray
This alluring town lures leaf-peepers with foliage in the Shenandoah Valley. Carpeting the Blue Ridge Mountains on the east and the Massanutten Mountains on the west, be sure to drive Skyline Drive on an imminent fall escape. The Shenandoah River laces the town south, weaving around the Shenandoah National Park. Together with the George Washington National Forest to the north, they add 60,000 acres for camping, hiking, horseback riding, fishing, hunting, and mountain biking.
But wait, there are the largest and most popular caverns in the eastern US. The Luray Caverns is a massive underground lair, with 140-foot natural columns, colorful stalactites, and brick walkways, plus the Great Stalacpipe Organ, the world's largest musical instrument, using stalactites as its "pipes." Hungry for more? In addition to the Appalachian Trail access, Cooter's Place is a roadside attraction to the west for shopping, dining, and a museum, all dedicated to The Dukes of Hazzard TV series.
South Riding
Looking past an offbeat name, just a geographic reference that stuck, South Riding is a typical, albeit planned, community in an older area of Loudoun County, with a larger population in the 30,000s. The extraordinary lies mere minutes southeast. Foamhenge is a fun replica by eccentric Virginia artist Mark Cline of Stonehenge made entirely of foam. This quirky installation is a play-up of the original through art in a lighthearted atmosphere to wander around the foam pillars, taking pictures.
Nearby, the National Botanic Garden is a treasure trove of natural beauty and creative design. Every turn is a visually intriguing physical experience and a perfect portrait of grandeur for photography. From the vibrant florals, cacti, trees, and serene bamboo groves to a man-made mountain and castle, plus a hobbit land, it is too much whimsy in one place. The not-for-profit garden operates on merit for public pleasure and hosts events a few days a month, April to November. Check the website when it opens.
Staunton
Staunton, “One of a Dozen Distinctive Destinations in the United States,” warmly embraces travelers alike in the heart of the forever beautiful Shenandoah Valley. What earned it the prestigious ranking by the National Trust for Historic Preservation? Take a memory-lane trip down the main street, Virginia's first to receive a “Great American Main Street Award.” Its architectural landscape is second to none—through no less than five historic districts—with magnificently designed and preserved buildings.
The historic facades glean admiration, housing 100+ unique shops, art galleries, and hip restaurants in the compact downtown. Supplement shopping and dining with Blackfriars Playhouse, modeled after England's, or tour the Woodrow Wilson Presidential Library and Museum at his birthplace. The outdoor Frontier Culture Museum reveals how it all started, from the arrival of the German, English, and Irish settlers. Finally, score a lodging in one of Staunton's nine beautifully restored B&Bs.
Virginia is no stranger to illustrious towns and strange landmarks, offering an amazing way to discover US history and culture that is fun for everyone. These enticing characters blend history and hospitality with scenic beauty, delivering a refreshingly authentic take somewhere between the Atlantic and the foothills.
This graceful state with history, Southern vibes, and splendidly diverse natural beauty is equal parts playful and peculiar. Virginia draws eccentricity from everything. From wild ponies to Foamhenge, you just have to hop off the beaten path to experience its one-of-a-kind humor, generously sprinkled throughout.
