9 Best Things to Do in Shepherdstown, WV

September 20, 2024

West Virginia’s oldest town is full of new life for visitors looking to delve into a piece of American history. Detour to Shepherdstown during your visit to Harpers Ferry, less than a dozen miles away, to experience more than three centuries of history.

Discover a town reborn after being occupied as a Civil War field hospital. Wander historic streets past structures which have been there since the early 1700s. Experience scenic views of the Potomac River.

Guests staying in our Harpers Ferry cabins and vacation homes are just a short drive away and have plenty to fill their day with these popular activities.

1. Explore the Historic Downtown District and German Street

Afternoon strolls down German St. will take you through the heart of downtown Shepherdstown. Buildings preserved from the 18th and 19th centuries line the street, creating a pleasant small-town charm any visitor will fall in love with. Wander past friendly locals dining on sidewalk patios, admire unique store signs hanging overhead, and gawk at creative storefronts. Pop your head into quaint boutique shops for antiques, artisan goods, collectibles, tasty treats, and more.

Here are a few local spots you don’t want to miss:

Have lunch downtown at popular restaurants, including The Press Room and Blue Moon Cafe.

2. Discover the True Origin of the First Steamboat

Did you know one of America’s greatest inventions was created in Shepherdstown? James Rumsey sailed the first steamboat on the Potomac River near Shepherdstown in 1787, 20 years before Robert Fulton invented the more commercially successful version. Shepherdtown preserves the steamboat’s real history with several local landmarks.

Visit the James Rumsey Monument, perched on a hilltop overlooking the Potomac River. It’s one of the best views of the river, the state of Maryland on the other side of the Potomac, and the Blue Ridge Mountains. Find the historical marker at the start of the James Rumsey Bridge and walk across to enter Maryland. See a working replica of the steamboat James Rumsey used inside the Rumsey Steamboat Museum.

3. Sightsee on a Self-guided Walking Tour

The best way to get to know Shepherdstown is on foot. Park at the metered parking on German St and explore for a couple of hours on a self-guided walking tour.

Pick up a map at the Shepherdstown Welcome Center Downtown or use this free digital version. You’ll cover nearly 60 important historical sites with stops at the Shepherdstown Public Library, Mecklenburg Inn, Old Market Place, and Shepherdstown Opera House. You’ll be surprised at the rich history of these seemingly ordinary buildings.

Also, check out the Shepherdstown Ghost Tour to see if the ghost tales haunting many of these locations are true.

4. Recreation on the C & O Canal Trail

Rent bikes from Shepherdstown Pedal & Paddle and explore the region’s once-vital waterway. The historic C&O Canal was used during the 19th century for transporting goods between Washington DC, and Maryland. Today, it’s one of the best things to do in Shepherdstown for hikers, cyclers, and boaters to get fresh air.

The hiking and biking trails follow the C&O Canal Towpath, part of the Chesapeake and Ohio Canal National Historical Park. Cycle to Snyder’s Landing on a guided trip or challenge yourself to the 13-mile ride to Harpers Ferry. Take a hike with a view along the Potomac River or cool off while kayaking the C&O Canal.

5. Brews with Views at the Bavarian Inn

Photo Credit: Ron Cogswell via Flickr CC 2.0

The owners of the Bavarian Inn bring their European heritage to West Virginia. They’ve transformed this hilltop manor into a 12-acre complex featuring the best views and brews in town. Visit the property to indulge your taste buds in homegrown flavors.

The Bavarian-style architecture of the inn is a nice complement to the historic colonial American architecture seen throughout the rest of town. Taste German culinary specialties like schnitzel, Bavarian sausage, and sauerbraten inside the AAA Four Diamond Award-winning dining room.

Taste seasonal brews crafted by Bavarian Brother’s Brewing, one of the top breweries in Jefferson County. One of Frederick, Maryland’s leading design firms created this contemporary rustic brewhall setting with an outdoor beer garden all within the Bavarian Inn grounds.

6. Browse Artifacts in the Historic Shepherdstown Museum

Colonial settlers arrived in the Shenandoah Valley in the early 1700s, bringing German influence to the area now known as Shepherdstown. The Historic Shepherdstown Museum houses artifacts dating back more than 300 years.

The Entler Hotel houses this history museum, which holds timeless local and Jefferson County objects. It has grown its collection since opening in 1983, with exhibition displays now spread across two floors. See the Shepherdstown Clock, Civil War weapons, colonial-era furniture, an archive of historic photos, and Native American objects from before settlers arrived.

7. Pay Tribute at Antietam National Battlefield

The area surrounding Harpers Ferry and Shepherdstown hosts a number of Civil War battlefields.

Follow the Shepherdstown Pike 10 miles northeast to the Antietam National Battlefield in Sharpsburg, MD. It’s the site of the bloodiest single-day battle in US history, where nearly 23,000 soldiers were wounded, missing, or killed during the Civil War. The grounds are now part of the National Park Service and open to visitors.

These somber grounds are often full of Civil War enthusiasts uncovering the stories of that terrible time. Learn about the tragic events of September 17, 1862, in the museum exhibitions inside the visitor center. Explore self-guided hiking trails across the battlefield to put yourself in the boots of fallen soldiers. If you need a pick-me-up afterward, stop in at the winery next door!

8. See a Play at the Contemporary Art and Theater at Shepherd University

Shepherd’s university has a new attendee. But you’re here for entertainment instead of studies. The Contemporary Art and Theater program puts on Broadway and Off-Broadway performances right here on campus.

See world-class acting talent at a live show. This stage has seen everything from original commissions performed by the university’s theater troupes to a show-stopping presentation of Julius Caesar by William Shakespeare.

Are you visiting Shepherdstown during the Summer? Attend a screening during the Contemporary American Theater Festival. The New York Times ranked it among the top theater festivals in the US, with premiers of new plays, lectures from creatives, and open discussions with the audience. Ask a question for your 15 seconds of fame.

9. Picnic in Morgan’s Grove Park

Plan your vacation picnic in Morgan’s Grove Park. It’s 20 acres of prime park landscape are just 20 minutes away from Harpers Ferry. Bring a blanket for a traditional picnic in the grass under shady trees. Or claim one of the tables beneath the picnic pavilion.

Prepare by shopping local for picnic treats at the Shepherdstown Farmers Market. Every Sunday morning between April and December, visitors can shop more than a dozen local vendors for all the picnic essentials. Pick up bread and pastries from Philsonz Pharmacy Bakery. Sweeten your meal with organic honey from Shade’s Farm. Sample gourmet dips from the Cottage of Herbs.

Stay Near Shepherdstown

Go from the past to modern luxury when you check into our Harpers Ferry cabins, designed for refined comfort. It’s the perfect location for exploring Shepherdstown, Charles Town, and other top destinations in Jefferson County.