This Trio Of Charming West Virginia Towns Make For Unique Excursions

By Kathryn Streeter

From the greater Washington, D.C. region, hit the road for a scenic road trip. When you want to escape the bustling metropolitan area of D.C., consider road tripping your way through the nearby pastoral towns of Shepherdstown, Charles Town, and Harpers Ferry in West Virginia.

Feel your shoulders relax as the bright lights fade into the rearview mirror. Prepare to stroll cobblestone sidewalks with ice cream, take in seasonal theater shows, or go kayaking. Here’s what you need to know to make your road trip to this trio of storied historic towns unforgettable. 


Established in 1730, Shepherdstown is the oldest city in West Virginia. Reflecting a blend of old and new, it’s home to Contemporary American Theater Festival — part of Shepherd University — which seasonally features six modern productions. Check out the weekend Shepherdstown Farmers Market nestled downtown behind the library. The market offers a colorful array of produce from local farms and more such as fresh dips, spice blends, and teas courtesy of The Cottage of Herbs.

You’ll also find organic baked breads from Stone Hearth Bakery and Middle Eastern foods served up by Teyta’s Treats, an establishment founded by U.S. military veterans. As you explore town, boost your mood at Rock Hill Creamery where ice cream is whipped up on the premises, offering lavender honey, toasted marshmallow, or vegan-friendly Horchata sorbet flavors.

Join locals for happy hour at Mecklenburg Inn, site of a hospital during the Civil War.

Fun fact: This popular watering hole, dubbed the “Meck,” gets its name from the town’s founding name "Mecklenburg" — which changed to Shepherdstown in the late 1700s. 

Charles Town

Indulge in a signature sundae at ice cream cafe The Caverns, named after the once-popular, 200-foot-long cave and underground river below the town. Walk the main drag of West Washington Street, popping into the Charles Town Visitors Center for a self-guided walking tour map of the area.

At Cool Spring Nature Preserve, families can pick and choose from a potpourri of educational offerings or opt to freely wander the 63-acre footprint known for exceptional bird-spotting and great hiking paths. For lovers of the stage, enjoy a memorable performance at The Old Opera House Theatre Company, established in 1911, and one of the nation’s oldest continuously operating venues.

For the evening, book ahead for a memorable dining experience at the Hillbrook Restaurant. The restaurant’s culinary concept is the brainchild of internationally acclaimed executive chef Jan Van Haute, whose goal is to add a distinct flair to the ever-growing foodie scene of the area. 


Harpers Ferry

Enjoy the great outdoors by hiking the 4-mile stretch of the Appalachian Trail which winds through town. On this small portion of the 2,178-mile hike lies the Appalachian Trail Conservancy — an iconic stop because it marks the exact halfway point of the legendary hike.

Catch your breath while visiting exhibits in historic Harpers Ferry to grasp its importance in the Civil War. If your flavor of fun is in the water, tubing and kayaking is possible through River Riders. For fly-fishing enthusiasts, White Fly Outfitters offers equipment and expertise to ensure you score some smallmouth bass.

And at the end of the day, raise your glass at The Barn, where local craft beer is poured a-plenty and live music may get you dancing.