Town guide: Shepherdstown
West Virginia’s oldest town treats you to sophisticated restaurants, colonial ambience and Old World elegance.
Dining
When it comes to meals, you’re spoiled for choice in Shepherdstown. Blue Moon Cafe serves indulgences like baked brie on French baguettes, crab melts, imaginative salads and signature sandwiches that overflow with fresh ingredients. Dine outside and listen to Town Run creek burble past your table!
Another pleasing dining option is Maria’s Taqueria. 
Their fresh Tex-Mex dishes are delicious and affordable— a win win! Locals enthuse about the fish tacos (served with garlicky aioli sauce). Melty Cuban sandwiches and traditional tacos drizzled with homemade salsa verde are big hits, too. Just make sure you save room for Maria’s famous coconut pie.
For more upscale dining experience, head to the Bavarian Inn Dining Room for award-winning wiener schnitzel and German sausages. There’s also The Press Room, which serves sophisticated contemporary creations. Try their decadent Lavender Creme Brulee!
Entertainment
Shepherdstown enjoys the distinction of being one of the most haunted towns in America. (All that history, you know?) If you’re into ghosts, don’t miss the Shepherdstown Mysteries Walk. A guide will tell you all about local lore, creepy tales and intrigue. Maybe you’ll even hear something about elephants, too. As darkness sets in, tour the Old English Cemetery for orbs and resident spectres.
The Shepherdstown Opera House has old bones but youthful spirit. Built in 1909, this elegant theater hides a packed schedule behind its narrow facade. Order tickets for year-round entertainment, movies, music and shows!
Wet your whistle at the Mecklenburg Inn, a favorite local watering hole. Its pressed tin ceiling, dark wood paneling and intimate interior have an age-soaked patina that only comes from time. In fact, the “Meck” once served as a Civil War hospital. Pull up by the bar and order beer, mixed drinks and burgers. Or sit by a bamboo grove in the courtyard. If your timing is just right, you can hear live music and open mic performances, too.
Shopping
There’s nothing like settling into a hotel with a fresh novel. Four Seasons Books is your place to get new and used classics, fiction, biographies and more! They also have frequent events with authors, book talks and poetry recitals.
Dickinson & Wait Craft Gallery is a definite crowd pleaser. In fact, the American Made Show has made it one of the Top 100 Retailers of 
American Crafts 3 separate times! Come inside for a clever, colorful selection from local artists. You’ll find original landscape paintings, pottery, jewelry, kooky sculptures and whimsical watches.
No trip to Shepherdstown is complete without a detour to O’Hurley’s General Store. It’s like a frontier time capsule, or something from “Little House on the Prairie”! Wander aisles stuffed with anything from glassware and jeans to fruit presses, coffins and dolls. On Thursday nights, the shop squeezes in live Celtic and traditional music, too.
Recreation
Get to know Shepherdstown even better— go by bike or by boat! Shepherdstown Pedal & Paddle is your one-stop-shop for outdoor adventures. Pick your choice of transportation and rent kayaks, tubes, and bikes. From there, explore Antietam Battlefield and miles of scenic rivers. Knowledgeable staffers can also arrange a shuttle service for you— just ask them about their package deals.
History
Ever since its birth in 1762, this panhandle town has seen quite a lot. The Shepherdstown Museum helps put all that history into context for you. Located inside the Entler Hotel, it catches your attention with its elegant dining room. You’ll easily imagine yourself arriving to a 19th-century dinner party. At least, that’s the idea behind the quaint 1847 setting.
And upstairs, you’ll get to wander a haunted bedroom. Back in 1809, a local died here after a dramatic duel. Maybe you’ll meet him! Other museum curiosities include a mail wagon, rifles and Civil War artifacts.
Extend your trip back in time— go on a walking tour. The museum’s site has digital and print maps you can download.
Where to stay
One of Shepherdstown’s most romantic B&Bs is the Thomas Shepherd Inn. This Federal-era home has charming original hardwood floors and attractive 19th-century decor. Settle by the fireplace, snack on afternoon cookies
or snuggle on large, feather-topped beds. You also get bedside chocolates, robes and a full breakfast. Ready to settle in?
The Bavarian Inn is an upscale hotel with unusual amenities. Its claim to fame: an infinity pool that seemingly melts into the Potomac River. When you’re done swimming, relax with a drink at the bar. Inside, order award-winning German cuisine and desserts. Menu highlights include wild game meatloaf, sauerbraten, and apple strudel. Please note that after 5 p.m., you should dress up for indoor dining.
This post was last updated on March 16, 2022