This 300-year-old town has kept up with the times with ease–all thanks to a dedicated community.
photographed by NIKKI BOWMAN MILLS & CARLA WITT FORD
Oldest Town in West Virginia, Most Haunted Town in America, and Birthplace of the Steamboat—Shepherdstown has plenty of reasons to brag. But ask anyone who’s been to this quaint river town, and they’ll tell you its greatest attraction is the people.
“We’re really involved. We’re invested in what Shepherdstown really is,” says town council member Jenny Haynes. “We can all think different things but still get along and meet for coffee at Betty’s at the end of the day. That’s what I love about Shepherdstown—we’re a mixed bunch.”
Established in 1762—and briefly a leading contender for the nation’s capital—this Jefferson County town was once a settlement rooted in travel, hospitality, and commerce. Nearly 300 years later, at 1,500 residents, it still is.
What’s Here?
Shepherdstown packs a lot into half a square mile. Settle in for your stay at the Bavarian Inn, Resort and Brewing Company, then stroll through the Shepherdstown Historic District. Peer into the past with landmarks famous for their history and architecture, like Baker House, a 1790s Federal house that was once the home of U.S. Congressman John Baker. Entler Hotel and Historic Shepherdstown Museum, built in 1786, served as a hospital and Union soldier quarters during the Civil War. Visit The Mecklenburg Inn, built in 1790 and now an English pub with an outdoor garden courtyard, or catch a movie or musical performance at the 1910 Shepherdstown Opera House.
Its history is rich, but this town is anything but stuck in the past. “It’s the history that makes us,” Haynes says. “We’re not scared of change—we want to be in charge of it.”
Stop for a bite, and you’ll understand how this old town stays so chic. Indulge in award-winning reimagined Appalachian cuisine at Alma Bea, or find French fare at Bistro 112. Blue Moon Cafe is a local favorite for sandwiches, soups, and salads, and The Press Room dishes out New American cuisine. The Bavarian’s new brewpub and lounge is a popular place to enjoy craft brews, fine wine, and delicious food. Looking for baked goods? Shepherdstown Sweet Shop Bakery has satisfied sweet tooths for more than 40 years. After exploring the picturesque streets, treat yourself to a cone at Rock Hill Creamery or a pick-me-up at Lost Dog Fine Arts, Coffee & Tea. Many shops have been around for decades, according to Haynes, investing in the local community.
If quaint shopping is what you seek, look no further. Dogwood General Store and O’Hurley’s General Store offer eclectic artisan goods, while Dickinson & Wait Craft Gallery spotlights this small town’s huge art scene. Stock up on fresh goodies at Community Garden Market, then find your people at Four Seasons Books’ many book clubs.
What’s Near?
Situated on the banks of the Potomac River just 90 minutes from Baltimore and Washington, D.C., Shepherdstown has amenities nearby for every outdoor enthusiast, urban explorer, and history buff.
Explore the C&O Canal Towpath by foot or bike with a rental from Shepherdstown Pedal and Paddle, or grab a kayak or inner tube for thrills on the Potomac River. Hiking and watersports not your thing? As a central point of eastern Civil War battles, Shepherdstown has easy access to Civil War landmarks like Antietam National Battlefield and Harpers Ferry National Historical Park. Thanks to this regional history and associated folklore, haunted attractions like candle-lit ghost tours are abundant.
“People love it here,” says Christian Asam, president of Bavarian Inn. “Our small-town charm, our proximity to battlefields, the river, the C&O Canal, and the university—Shepherdstown has seen remarkable growth in the last 45 years, and it’s become a destination.”
Why Stay?
If great food and endless activities don’t convince you, Shepherdstown’s buzzing economy and family-friendly atmosphere should tip the scales.
Tied closely with the town’s history, Shepherd University offers more than 80 programs of study and is known for its tight-knit student body and career opportunities. “Shepherdstown is clean, it’s safe, it has great schools,” says Asam, who grew up in town and now raises his children there. “There are so many social and service groups, and the university brings a level of sophistication to the town you don’t find in many others.”
Art, history, and community here culminate in annual festivals like the American Conservation Film Festival, Contemporary American Theater Festival, Christmas in Shepherdstown, and BooFest.
“When you come to Shepherdstown, you never know what you’ll find,” says Haynes. “But you do know you’re going to get all these little bits of happiness.”
Why Now?
“Shepherdstown is really having a resurgence,” says Asam. “As far as cycles go, we’re on the upward trend or a peak, and it’s great. I think visitation has been high ever since the pandemic, and it continues to be a success story.”
In Best of West Virginia 2024, the town received Best Town for the Arts for the second time and Best Downtown Shopping for the first time. Other exciting developments include the recently opened Shepherdstown Visitors Center in the historic Market House—be sure to stop in—and the upcoming installation of an iconic Almost Heaven Swing at James Rumsey Monument Park. To support its fabulous downtown, Shepherdstown is also improving sidewalks. Beautification efforts like these don’t just support tourists—first, they support locals, and locals give back in turn. It all comes down to the people.
“We have a couple who visits four times a year. They’ve made so many friends, and they feel like family,” says Asam. “They always find such welcoming, great people in Shepherdstown.”
READ MORE ARTICLES FROM WV LIVING’S SPRING 2025 ISSUE
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