The 'Oldest Town In West Virginia' Is A Modern Mix Of One-Of-A-Kind Restaurants, Inns, And Quirky Shops

From wooded Appalachian trails to one of the most important towns in American history, West Virginia really has it all. Charming towns and scenic highways in the Potomac Highlands beckon you to explore, and tucked along the Potomac River, in the Eastern Panhandle, is Shepherdstown — a bustling community with small-town charm. Named in honor of its founder, Thomas Shepherd, the earliest record of a settlement there dates to 1730, earning Shepherdstown the distinction of being "the oldest town in West Virginia."

An abundance of museums and a stunning historic district provide ample distraction for history geeks, while outdoor enthusiasts can take advantage of the Potomac River's proximity for kayaking, canoeing, and a refreshing swim. Hop on a bike or slip on your best walking shoes to venture through the nature trails around town, and you'll even catch a glimpse of the old Railroad Bridge crossing the river. Mechanical engineer James Rumsey launched America's first steamboat on the Potomac at Shepherdstown in 1787, and the James Rumsey Monument commemorating the event doubles as a tranquil forested park to wander and admire river views.

Anyone who thrives on all things mysterious and ghostly will be pleased to hear that Shepherdstown is among America's most haunted destinations. Part of the West Virginia Paranormal Trail, visitors can join the Shepherdstown Mysteries Tour for a spine-chilling look around the town's spookiest locales. Not a fan of the paranormal? Take yourself shopping at one of the quirky boutiques around town, where you'll find vintage books, vinyl records, and seasonal decor. Historic inns with old-world charm also invite you to spend the night, meaning you'll have more time to explore Shepherdstown's unique dining scene, including everything from Parisian bistros to cozy English pubs.

A witness to the upheavals of the Civil War, Shepherdstown is a history lover's delight. Spend the day touring the exhibits of the Historic Shepherdstown Museum, situated within the Entler Hotel downtown (which may or may not be haunted). Civil War artifacts, antique furniture, and memorabilia are displayed amidst the historic hotel's former bedrooms and halls, taking you on a fascinating journey through time. Meanwhile, maritime aficionados should head to the Rumsey Steamboat Museum to see the working replica of James Rumsey's historic invention before wandering over to snap photos at the "Little House," a miniature cottage built in the late 1920s.

For more Civil War history, head to the Antietam National Battlefield over in Maryland, a mere 10-minute drive from town. There, you can hike the battlefield loop trails past historic farmhouses and rural landscapes, fish in Antietam Creek, or cycle the bike paths for a memorable day out. 

Then, head back to Shepherdstown to find yourself a scrumptious meal. With its quaint brick exterior and lively atmosphere, The Mecklenburg Inn is loved by locals (who affectionately call it "the Meck") for a good drink and hearty pub grub. Built during George Washington's presidency, this historic eatery also features an open courtyard where you can dance like nobody's watching. For an upscale Parisian vibe, just down the street is Bistro 112, equally praised by both locals and visitors. The menu there includes everything from lunch and dinner options to aperitifs and charcuterie boards. The escargot platter is a popular choice, or you can play it safe with some classic French toast. For dessert, head over to Rock Hill Creamery, which visitors claim is a must-visit spot. Sweet sorbets and zingy, handmade ice cream flavors will leave you coming back for more.

Being surrounded by nature on all sides means endless outdoor adventure is not far behind when in Shepherdstown. Take your bike for a spin through the peacefully wooded trails of the C&O Canal Towpath, which follows the course of the Potomac River. Shaded by leafy trees and boasting stunning river vistas, this trail promises to be a thrilling ride. For a splashing good time, book a kayak trip directly in town and float down the river with stops for fishing, picnics, and swimming.

Visitors can also catch a glimpse of the Blue Ridge Mountains from South Mountain State Park in Maryland, located roughly a 30-minute drive out of town. Hike parts of the Appalachian National Scenic Trail for breathtaking views from the mountaintops, and explore the tranquil woods around South Mountain where Civil War soldiers once fought a historic battle. Better yet, bring your tent and gear with you to spend an outdoorsy night at one of the park's designated campgrounds. A little over an hour away, also in Maryland, you'll find fishing, boating, and hiking opportunities galore at Rocky Gap State Park, a canyon lake paradise.

All that adventuring will surely leave you in need of a good night's rest. Thankfully, cozy accommodation is abundant in Shepherdstown. A soft bed can be found at The Bavarian Inn, a charming alpine chalet overlooking the Potomac River, where guests can enjoy refreshments by the infinity pool, or snuggle up by the fireplace at one of the suites. Meanwhile, the Thomas Shepherd Inn offers quaint guest rooms set within a historic Federalist-style manor dating to the 1860s, guaranteeing a night filled with Southern charm.