The mystical Shenandoah Valley spans nearly 200 pastoral miles from Harpers Ferry, West Virginia in the north to Roanoke, Virginia in the south. Along the way, it follows the undulating curves of the Blue Ridge and Allegheny Mountains as well as the sinuous lines of the Shenandoah River. Set against this spectacular backdrop, a sprinkling of towns grace the valley. Historic and charming, they are ideal for weekend getaways, outdoorsy pursuits, and plenty of surprises (including one of the country’s finest Shakespeare theaters). Here are some of the coolest towns in the Shenandoah Valley, from north to south.
Shepherdstown, West Virginia
Perched alongside the Potomac River, this artsy little college town, founded in 1730, offers an Americana downtown filled with boho shops, tucked-away restaurants, and cute little B&Bs. The Chesapeake & Ohio Canal awaits nearby, its towpath a joy to bike and hike. But what’s most surprising is Shepherd University's Contemporary American Theater Festival; for more than 25 summers, it has premiered six cutting-edge plays from the likes of playwrights such as Sam Shepard and David Mamet, with New York actors tackling the challenging and provocative new works. Be there in July to see the action, though the town offers plenty to enjoy the rest of the year as well.
Established in 1798, Berryville prides itself on its lost-in-time look, with beautifully preserved Civil War–era buildings edging tree-shaded streets. But it’s not just about the past here. There’s an active arts scene—with the Barns of Rose Hill offering concerts, classes, performances, and films—as well as music festivals, including Watermelon Park Fest and Pasture Palooza. Several wineries sprinkle the town's outskirts, and the pick-your-own Mackintosh Fruit Farm offers a seasonal array of fresh fruit. Nearby, Holy Cross Abbey is a popular stop for abbey-made fruitcakes, honey, and chocolate truffles. Meanwhile, the Orland E. White Arboretum is the State Arboretum of Virginia, and is especially spectacular in autumn.
If you’re in the market for vintage clothing, antique furniture, long-forgotten art, or any other kind of vestiges from the past, add Strasburg to your list. Settled by Germans in the late 1700s, this little town is known for its antiques, with 60-plus vendors offering up curios at the Strasburg Emporium. But contemporary art has found its way here, too, as evidenced in its colorful murals scattered along King Street and the creative works on display at the Shenandoah Museum of Contemporary Art. Strasburg is also home to bustling breweries, cafés, restaurants (check out Old Dominion Doggery, whose hot dogs are locally sourced and can be ordered in creative flavor combos such as the Elvis Dog), the historic Hotel Strasburg (which served as a Civil War hospital), and the Grilled Cheese and Tomato Soup Festival in November.
Front Royal, Virginia
The northern gateway to Shenandoah National Park, this bustling little town is all about the great outdoors. Even if you didn’t count the national park among its blessings, you have kayaking, rafting, inner tubing, horseback riding, and golfing all within close proximity. Front Royal's downtown thrives with outfitters, along with a fair share of eateries, boutiques, and museums delving into local Civil War history. And if you’re still looking for something to do, Skyline Caverns is a good alternative to nearby Luray Caverns.
New Market, Virginia
This little town, with its wealth of historic architecture, dates back to 1796. Strolling downtown, be sure to check out the Jon Henry General Store, which features a ridiculously extensive socks collection and old cigarette machine that has been converted into an “art dispenser.” If baseball is your thing, the New Market Rebels and Shockers baseball organizations play some really good ball, the latter being one of the nation’s oldest running leagues. That said, the town is best known for the Civil War’s Battle of New Market. You can learn more at the battlefield, as well as at the Virginia Museum of the Civil War and the Strayer House Civil War Orientation Center.
Tourists flock to Luray for its famous caverns, the largest in the eastern U.S. As spectacular as they—and the famous Great Stalacpipe Organ—are, all the action isn’t below ground. Small-town aficionados will be charmed by downtown Luray’s collection of 19th-century buildings, which house restaurants, one-of-a-kind shops, and galleries. Knickknack-filled Gathering Grounds is a cozy place for homemade fare, while Hawksbill Brewing Company uses locally-sourced ingredients such as blackberries and honey to brew its craft beers. And if that’s not enough to keep you occupied, Shenandoah National Park awaits a hiking boot’s throw away.
If there was a template for adorable historic towns, Staunton would be it. The town’s beautifully restored turn-of-the-20th-century architecture perches alongside hilly streets in five different neighborhoods. You can join a free Saturday tour with Historic Staunton to learn more, or simply stroll along Beverley Street, looking up to admire the gorgeous Italianate, Romanesque Revival, Greek Revival, and Beaux Arts façades. Meanwhile, the American Shakespeare Center presents creative renditions of Shakespeare's works as the famous playwright would have directed them—including audience participation—in the world’s only replica of London’s Blackfriars Playhouse. Later, if you can get reservations, venture beyond town limits for dinner at the 26-seater The Shack. And the Stonewall Jackson Hotel is a local landmark, the perfect place for a drink or an overnight stay.
Sitting at the sweet spot where Shenandoah National Park, the Blue Ridge Parkway, and the Appalachian Trail intersect, this charming little valley town clearly is an outdoor lover’s paradise. Cutting right through Waynesboro, the South River is within even closer proximity, providing a water trail for locals to boat and fish. But the town is artsy, too, with offerings including the Shenandoah Valley Art Center, P. Buckley Moss Gallery, the newly renovated Wayne Theatre, and fascinating murals and public art.
No doubt the presence of the historic Virginia Military Institute and its youthful cadets give Lexington its vibrancy. You’ll discover buzzy cafés, bookstores, and breweries along a couple quick blocks, while summer evenings are spent at Hull’s Drive-In or the outdoor Lime Kiln Theater. Perched along the Maury River, Lexington also is an outdoor hub, with hiking, paddling, and biking all within easy reach. Don’t forget nearby Natural Bridge, a rock formation once owned by Thomas Jefferson.