Photograph courtesy of Chris Weisler
Shepherdstown may be West Virginia’s best-kept secret. The oldest town in the state and home to Shepherd University, it sits along the Potomac River right across from Maryland and holds a rich history, from its official founding in 1762 as Mecklenburg to its town-wide transformation into a field hospital for hundreds of wounded soldiers during the Civil War. Many of the downtown buildings along German Street (named for the predominantly Germanic original settlers) are centuries old, giving it an enchantingly old-fashioned feel. But there’s much more to recommend the locale than simple small-town allure. Shepherdstown’s got unexpected character—it’s artsy, eccentric, even bohemian. A stroll down its main street reveals an eclectic mix of businesses including an apothecary, studio galleries, and a handful of shops selling trinkets, tonics, candles, and crystals. Many restaurants boast backyard patio gardens, and painted benches line the street for optimal relaxation and enjoyment of this warm and welcoming downtown.
Friday
Photograph courtesy of Chris Weisler
CHECK IN ➞ Family-run for almost 50 years, the Bavarian Inn feels like a charming chalet in the mountains of Germany. The 72-room hotel on the banks of the Potomac River comprises several Alpine-style lodges, some with suites featuring giant Jacuzzi tubs and gas fireplaces, and all with private balconies. During the warmer months, an infinity pool with resort-style amenities is a popular spot for pre-dinner drinks and views of the rolling hills of the Shenandoah Valley. And the rustic-chic brewpub with a spacious patio and fire-pits presents German-inspired specialties, such as Wiener schnitzel, a sausage sampler, and craft beer from on-site Bavarian Brothers Brewing.
EVENING ➞ After dropping your bags—and maybe taking a quick sunset dip—head to dinner at Bistro 112. The French restaurant is situated in a quaint historic building downtown, but dining in the secret-garden-like patio out back is a must. Enjoy dishes such as escargot, duck leg confit, and bouillabaisse paired with French vintages to achieve the authentic European experience envisioned by classically trained chef Jan Van Haute.
End your evening at the Mecklenburg Inn, aka the “Meck,” a 21-and-over English pub established circa 1793. Though it’s technically an inn, most people here are not staying the night (there are only three rooms) but are likely locals having a few pints of Guinness in the dimly lit taproom or the patio garden.
Saturday
MORNING ➞ Start your day with a simple breakfast at MJ’s on German DeliCafe, a homey, family-run establishment serving up egg sandwiches on locally baked buns, fresh smoothies, and huge mugs of steaming coffee.
After that, drive down the road to Elmwood Cemetery, where more than 250 Confederate soldiers are buried—many of whom died in nearby Antietam, site of the bloodiest battle of the Civil War. Many Shepherdstown homes and businesses served as makeshift hospitals following the fighting, and this cemetery serves as the final resting place of those who passed. You can also find headstones of veterans from the Revolutionary War, the War of 1812, and both world wars.
Photograph courtesy of Jefferson County Convention and Visitors Bureau
Next, head back downtown to Shepherdstown Pedal & Paddle, a full-service bike, kayak, and canoe shop offering gear rentals and expert guidance. Here, you can choose your own adventure: Pick out a kayak and gently float down a 20-mile, rapid-free section of the Potomac, or opt to cycle down the wooded, riverside C&O Canal Towpath (it was originally a walking path for canal mules as they pulled barges through the waterway).
AFTERNOON ➞ Lunch is at Blue Moon Cafe. The casual eatery features an extensive menu of burgers, wraps, and salads, but go for the house specialty crabcake sandwich. The tree-shaded backyard is a pleasant oasis, complete with a flowing stream, flourishing plants, and ample seating.
Stop in at the Historic Shepherdstown Museum, located inside the former 19th-century Entler Hotel, and check out a replica of the first steamboat invented by Shepherdstown resident James Rumsey in 1787.
Photograph courtesy of Mountaineer Popcorn
The shops along German Street capture the town’s eccentric personality. Line up at the window of the quirky Lost Dog Coffee Fine Arts Drink Emporium and order one of the cafe’s specialties: Owner Garth Janssen crafts excellent flavored espresso tonics and a perfectly balanced banana mocha. Trinkets galore, including delightful miniatures and kooky souvenirs, can be found next door at Creative Procrastinations & Whimsical Necessities. Browse new and used reads at Four Seasons Books, a female-owned independent shop that’s served as a cornerstone of the community for 35 years. And don’t skip Mountaineer Popcorn, where the small-batch popcorn is made with corn grown on the family farm. Creative flavors run the gamut from cheese pizza and loaded baked potato to cinnamon toast crunch and birthday cake.
EVENING ➞ When happy hour calls, walk over to the Press Room, named after the building’s earlier incarnation as a newspaper printing house from 1906 through the early ’70s. Exposed brick walls and a cozy 50-seat dining room lend a lovely ambience in which to savor international wines and appetizers such as raw oysters and pâté.
For dinner, make your way to Alma Bea, where James Beard Award finalist and West Virginia native Mary Ellen Diaz creates a mouth-watering menu of Appalachian-inspired small plates (affectionately dubbed “Tapa-lachian” cuisine), such as bacon-wrapped sugar toads (an East Coast puffer fish) and a venison patty melt. You can’t depart for the night without a slice of dessert from the packed display case, and the potato candy pie made with peanut butter mousse and chocolate cookie crust is a definite winner.
Sunday
Photograph courtesy of jonbilous/Adobe Stock
MORNING ➞ Start your day with views of the Potomac and a photo op on one of West Virginia’s popular Almost Heaven Swings (at roughly 50 scenic spots across the state) overlooking the Potomac at James Rumsey Monument & Park, where the inventor launched the first steamboat. Afterwards, pop into O’Hurley’s General Store (just a half mile away) to experience a true taste of nostalgia. Open for more than 100 years, the institution—which served as an ag supply depot and, later, a spot for gas and groceries—is today a variety store whose antique shelves are stocked with quite the assortment of wares, from jams and jewelry to hats and hardware. Say hi to Murphy, the shop cat.
On your way out of town, grab a quick breakfast at Bolivar Bread Bakery in neighboring Harpers Ferry. The female-owned shop bakes plenty of tasty pastries and breads, but do yourself a favor and order a pretzarolli, their take on the pepperoni roll, West Virginia’s state food. Snag a brown butter chocolate chip cookie or cream cheese–frosted cinnamon bun for the road.
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Adrenaline Rush
Three high-thrills activities—for those who dare—in nearby Harpers Ferry
Photograph courtesy of Jefferson County Convention and Visitors Bureau
LEAP ➞ Ever wanted to experience the heart-stopping feeling of a free fall? With the Great Bungee Company, you can. Choose a chest or ankle harness and say a quick prayer before launching yourself 150 feet over the shimmering waters of the Old Standard Quarry.
ZIP ➞ Fly through the treetops on a network of seven zip lines—including an optional, extra-exhilarating 50-foot downward plunge and a scenic 1,000-foot-long ride over the Potomac—at River Riders Family Adventure Resort.
RAFT ➞ River Riders also offers whitewater rafting adventures on Class I–III rapids. Enjoy the guided, two- to three-hour paddle along seven miles of the Shenandoah and Potomac rivers. For more chill and less thrill, opt for the flat-water tubing experience.
This article appears in the Fall 2026 issue of Southbound.
