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The 10 Most Enchanting Small Towns in the Shenandoah Valley

Anchored in frontier history, these small towns possess thoroughly modern charms.

Some places are bestowed with an abundance of blessings, and when it comes to small towns, one of those places is the Shenandoah Valley. This legendary valley splices down western Virginia (and a bit of West Virginia’s panhandle), a plush green expanse snaked by the legendary Shenandoah River and snuggled between the soft, rolling hills of the Blue Ridge and Alleghenies. Once the fledgling nation’s frontier and the scene of divisive Civil War battles, today its towns embrace the outdoor life, anchored by Shenandoah National Park; foodie restaurants, thanks to an abundance of local farmers and producers; vintage architecture; wine and beer trails; artsy galleries; and so much more. Whether you like to hike, eat, kayak, shop, wine-taste (or beer), admire historic buildings, shop, go to the theater, or simply soak in small-town charm, the Shenandoah Valley’s towns will enthrall you. Here are 10 of the most enchanting, from north to south.

INSIDER TIPI-81 races down the 140-mile-long valley, probably the prettiest interstate around. But to truly slow down, strike out on US 11, which takes you into the hearts of most of the small towns.


1 OF 10


WHERE: West Virginia

With its 200-year-old buildings and handful of streets, the river town of Shepherdstown feels like it should be a museum lost in time. Founded in 1730 along the Potomac River at the Shenandoah Valley’s northernmost tip, its history embraces colonial settlers, Revolutionary War fighters, wagon drivers, and Civil War soldiers. But Shepherdstown is firmly entrenched in the present. Boho shops, award-winning restaurants, and sweet B&Bs fill the historic buildings. The Chesapeake and Ohio Canal awaits nearby, its bird-serenaded towpath ideal for walking and biking. Perhaps most surprising, however, is that for the past 25-plus summers, the town has premiered edgy, challenging, thought-provoking plays at the world-famous Contemporary American Theater Festival, featuring New York actors. Here, too, the German-flavored Bavarian Inn provides Teutonic flair on the Potomac.

2 OF 10

Front Royal

WHERE: Virginia

A bit larger than most Shenandoah Valley towns (~15,000), Front Royal is the gateway to Shenandoah National Park. That explains the number of outfitters and sporting goods shops sprinkling its historic downtown. In addition to sublime hiking in the park, there’s also kayaking and canoeing on the nearby Shenandoah River, golfing, and horseback riding. But it’s not all about the outdoors. You’ll find a few memorable art galleries, including the Kiln Doctor, specializing in pottery and ceramics. The Civil War rampaged through here, with one of the more interesting sites being the Belle Boyd Cottage—she was a Confederate spy who used her wits to help Stonewall Jackson win the Battle of Front Royal for the South.

3 OF 10


WHERE: Virginia

Founded in 1798 at the crossroads of two colonial roads—Main Street and Buckmarsh Street—Berryville retains its historic charm. In fact, its historic district, filled with beautifully preserved 19th-century buildings, is listed on the National Register. But there’s more here than history. Concerts and performances fill the schedule of Barns of Rose Hill, one of the many places contributing to the town’s active arts scene. Wineries lace the Shenandoah Valley, including Berryville’s family-run Veramar Vineyard. And monks at Holy Cross Abbey live their days in the St. Benedict way: manual labor, praying—and making honey and traditional fruitcakes. Stop by to take some home.

4 OF 10


WHERE: Virginia

They call Strasburg “pot town” for a reason. No, it’s not the one you’re thinking. Earthenware pottery fueled this small town’s economy in the late 1800s. The Strasburg Stone and Earthenware Manufacturing Company, in the center of town where pottery was made, now holds the Strasburg Museum. You’ll learn about the pottery history, as well as the Southern Railroad (the factory later became a railroad depot), period rooms, and Civil War history. The historic downtown thrives with cafés, restaurants, and breweries. Suggestion: Stop by Old Dominion Doggery to sample one of its creative takes on hot dogs, such as the Elvis Dog (served with smashed bananas, chunky peanut butter, and bacon).

5 OF 10


WHERE: Virginia

Luray Caverns reign as the largest caverns in the eastern U.S., a fact that draws crowds of people to the small town of Luray. While the caverns are fascinating—especially the Great Stalactite Organ, the world’s largest musical instrument—the town itself has allure. Nineteenth-century buildings bustling with restaurants, one-of-a-kind shops, and art galleries fill its Americana downtown. Get revived at Gathering Grounds Patisserie and Cafe (don’t forget the croissant). The Shenandoah Heritage Village, next to the caverns, is an outdoor museum that showcases 19th-century frontier life; kids can even mine for gems. For anyone who’s a fan, Cooter’s Place just outside town relives Dukes of Hazzard with a replica of Cooter’s garage and appearances by the man himself.

6 OF 10


WHERE: Virginia

With six historic districts showcasing a spectrum of turrets, pressed metal, scalloped trim, and other architectural flourishes, set against a backdrop of vivid Blue Ridge views, this railroad town is constantly listed as one of the nation’s most beautiful small towns. It’s also a cultural haven. The American Shakespeare Center is the world’s only authentic replica of the indoor Blackfriars Playhouse; as in the Bard’s day, the audience always plays part in the show. A thriving foodie scene, sourced by local farmers and producers (and wineries), includes Zynodoa, showcasing modern southern cuisine; the playful and innovative Shack (just 26 seats—reserve far ahead); and the artsy coffee shop By & By, a place to hang out all morning (and then all evening at the outside beer garden). The grand-dame hotel is the gracious Hotel 24 South, a southern beauty featuring terrazzo floors, chandeliers, and wall sconces. Just outside downtown, the Blackburn Inn offers a boutique hotel and spa experience in a historic setting. The Virginia Scenic Railway, with trains departing from historic Staunton station, is the state’s only regular train sightseeing service; it offers two round-trip, three-hour excursions a day through the Shenandoah Valley.

7 OF 10

New Market

WHERE: Virginia

New Market’s sweet downtown reflects its German heritage, the simple vernacular structures best seen on a self-guided walking tour. Along the way, you’ll discover a small history museum, coffee shops, and a popular farmer’s market. Jon Henry’s General Store is a modern take on its original 19th-century purpose, purveying everything from vintage license plates to brooms to Fair Trade treats. The New Market Rebels and Shockers baseball organizations play some really good ball. All this said, most people know New Market for the tragic story of the VMI cadets—some no older than 15—who marched here from Lexington in 1864 during the Civil War to fight in the Battle of New Market, the Confederate’s last major victory. You can learn all about it at the New Market Battlefield and the Virginia Museum of the Civil War.

8 OF 10


WHERE: Virginia

Cadets and collegiates swarm about the historic town of Lexington, attending two deeply traditional colleges: Virginia Military Institute and Washington and Lee University. It’s interesting enough to stroll through the campuses, including VMI’s museum and W&L’s neoclassical buildings and the Watson Galleries, a stunning collection of Asian ceramics. But there’s so much more in this exquisite small town. Coffee shops, artisan stores, foodie restaurants, and one brewery occupy stately old buildings in the historic district’s several blocks. Confederate general Stonewall Jackson taught at VMI for 10 years before the Civil War; he lived at what’s today the Stonewall Jackson House, where Master Tours provide a deeper, more balanced view of history (i.e., they don’t glorify him and they speak frankly about the enslaved individuals who lived here). Lexington Carriage Company offers narrated, horse-drawn tours that give the 411 on town history. The lovely Georges Inn occupies three different historic buildings, each room custom-designed with exquisite taste.

Several breweries and wineries snuggled in the encircling emerald-green countryside include Devils Backbone Outpost Kitchen and Tap Room, Rockbridge Vineyard & Brewery, and Great Valley Farm Brewery and Winery—all with mind-blowing views. The surrounding hills and sparkling streams along the Upper James River Water Trail offer kayaking, horseback riding, and hiking.

9 OF 10

Buena Vista

WHERE: Virginia

Perched on the “sunset side” of the Blue Ridge, as they say, this mountain town is as picturesque as can be. The revitalized main street has shops, restaurants, and a bakery—though its greatest attribute is its nature. Green Valley was its name until 1888, after all. Immerse yourself in this natural splendor along trails in George Washington National Forest, along the Blue Ridge Parkway, or the Chessie Nature Trail, a 7-mile rail trail linking Buena Vista with Lexington along the Maury River.

10 OF 10

Natural Bridge

WHERE: Virginia

This isn’t your typical town. Natural Bridge is unincorporated and listed as the Natural Bridge Historic District. It centers on the stunning, 215-foot-high limestone arch rising above Cedar Creek once owned by Thomas Jefferson—he called it “the most sublime of nature’s works.” Indeed, the Natural Bridge is often touted as one of the “Seven Natural Wonders of the World.” Today, it is protected by a state park, offering 7 miles of woodland hiking trails, a Monacan Indian village, seasonal living-history programs, and one of the best dark-sky programs around.

As far as the encompassing historic district goes, it comprises 302 acres centered on the Natural Bridge and nearby Natural Bridge Hotel (which replaced the original hotel after a 1963 fire); it tells the story of the commercial and tourist development that sprang from the region’s natural beauty. Sprinkled throughout are several early domestic buildings, including the circa 1790 Barclay Tavern and circa 1900 Red Mill.