Attractions In And Around Shepherdstown, WV

If you’re in search of adventures or activities, choose lodging at the Thomas Shepherd Inn in Shepherdstown, WV, and you’ll be near a wealth of options including visiting Harpers Ferry and Antietam Battlefield.

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Movies, live music and/or theater can be enjoyed most nights of the week in and around Shepherdstown. Appalachian and heritage music happen in jam-session fashion at O’Hurley’s General Store every Thursday evening, and the Blue Moon Cafe features live music most weekend nights. The Opera House brings independent movies and foreign films to Shepherdstown every Monday. Community theater performances can be seen at the Full Circle Theater Company, the Old Opera House in Charles Town, and the Apollo Theater in Martinsburg. (more…)

In addition to the everyday activities available here, Shepherdstown is the site of several festivals. The renowned Contemporary American Theater Festival brings new American plays performed in repertory in July. Juried arts and crafts, along with West Virginia foods, are showcased at the Mountain Heritage Arts & Crafts Festival in June and September. Christmas, the Fourth of July, Easter and May Day bring parades and celebrations to the streets and parks of Shepherdstown. (more…)

The Shepherdstown area has many sites that played important roles in Colonial and Civil War era history. Antietam Battlefield, near the small town of Sharpsburg, MD, and Harpers Ferry, WV are only minutes away. Gettysburg, PA is just over an hour’s drive away. The Washington family (including George) left many footprints in the Shepherdstown area. (more…)

Outdoor activities are just minutes away. Hiking, biking, rafting, tubing, kayaking, golfing, and horseback riding are all available to you. The C&O Canal Path lies just on the other side of the Potomac River from Shepherdstown and the Appalachian Trail winds near Harpers Ferry about 15 minutes away. Several outfitters near Harpers Ferry offer various levels of raft, bicycle, tube and kayak trips. Add a few golf courses and horseback riding, and you can spend several days challenging yourself in the great outdoors while recuperating at the inn. (more…)

There are many shopping opportunities in and around Shepherdstown. Boutique locally-owned shops lining German Street purvey wines, American-made artisan crafts, bespoke jewelry and French-inspired decor. The Sweet Shop and our Sunday Farmers Market lets you bring a little taste of Shepherdstown home with you. (more…)

Spa Services
Spa and wellness services  are available at  locations in and around Shepherdstown. Facials, manicures and other beauty services are available along German and Princess Streets. In addition, you’ll find reiki, yoga, and other wellness practitioners in Shepherdstown and the surrounding area. (more…)

Several wineries offering tours and tastings are within a short drive from Shepherdstown. Most of the vineyards are located in Northern Virginia, just across the Virginia border from Harpers Ferry, near the small towns of Hillsboro, VA and Leesburg, VA. Some have terraces and patios with spectacular views, perfect for a bottle of wine and a picnic lunch. (more…)

Arts and Culture In and Around Shepherdstown, West Virginia:
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Shepherdstown is fortunate to have a thriving arts scene, with a variety of venues in the Eastern Panhandle of West Virginia area. Movies, live music and/or theater can be enjoyed most nights of the week in and around Shepherdstown.


Contemporary American Theater Festival and Shepherd University Theater

CATF celebrates over twentyfive years of producing new American theater in rotating repertory with music, art, lectures and readings to create the ultimate theater experience. The Festival runs during July with tickets going on sale in the spring. Visit their website for schedule info.

Shepherd University has a theater program with occasional performances during the school year. 

Black Box Arts Center, 113 S. Princess St, 304-870-4685.  Known as a place where local artists can come together to produce a variety of works (theater, music, and visual arts).  Programs vary throughout the year.  Visit their website for more information.

Old Opera House in Charles Town and Apollo Theater in Martinsburg

Two other community theaters make their homes in renovated historic buildings in the Eastern Panhandle, the Old Opera House in Charles Town, WV and the Apollo Theater in Martinsburg, WV. Visit the Old Opera House website for schedule info. Visit the Apollo Theater website for schedule info.

Live Music:

O’Hurleys General Store

Every Thursday night, local and visiting musicians perform Appalachian and heritage music at O’Hurleys General Store on Washington Street by the railroad tracks. Jay Hurley (born in the rooms above the store that he still lives in) doesn’t serve food or liquor, although sometimes there is hot chocolate warmed by the fire in the winter months. A great and absolutely free way to experience Appalachian music and local Shepherdstown color each and every Thursday around 7:30 p.m. Additional performances during Christmas in Shepherdstown.

Shepherd University Concerts

For classical, jazz and orchestral performances, Shepherd University’s world-class music department has ensembles that have performed all over the globe. Visit the website for schedule info.

Blue Moon Cafe, Mecklenburg Inn and other music spots around town

The Blue Moon Cafe has live music most days on the weekends, ranging from rock to bluegrass to blues.  Open Mic night is on Wednesdays from 9 – 11 pm.  Visit the website for more information.

The Mecklenburg Inn features open mic night on Tuesdays and live music on many weekends. (

Domestic offers live music, often jazz, on Sunday afternoons from 4 – 7 pm.


Opera House

Enjoy popcorn with real butter and your choice of wine, beer or soda with your movie or live entertainment just two blocks from the Thomas Shepherd Inn, at the Opera House. They offer live entertainment, both locally and nationally known, weekly. Movies every Monday. Visit their website for schedule info.

Shepherdstown Film Society

On many Friday nights a quality independent, foreign-language or classic film is shown free of charge by the Shepherdstown Film Society. Visit their website for schedule and location info.

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Upcoming Events In And Around Shepherdstown, WV:
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Free Jam Sessions – Every Thursday Night

Traditional Appalachian/Celtic Music at O’Hurley’s General Store. Enjoy listening to local musicians carrying on a 30-year tradition. (more…)

Free Movies – Friday Nights

The Shepherdstown Film Society offers screenings of classic films on Friday nights at no charge. (more…)

Movies and Live Music – Most Nights of the Week

The historic Opera House Theater offers live music or independent films in an intimate setting complete with buttered popcorn, wine, beer, and soft drinks. (more…)

Sunday Farmers Market – Every Sunday
Every Sunday, from late Spring until December, behind the Library on King Street from 9am until 1pm. Local farmers, bakers and crafts. (more…)

Contra Dancing – First Sat, Sep thru May
Traditional American country dance featuring New England-style contra dances and square dances with live music. (more…)

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Festivals and Celebrations In and Around Shepherdstown, West Virginia:
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In addition to the everyday activities of shopping, dining out and exploring the outdoors and history of the area, there are several long-standing fairs, festivals and tours in the Eastern Panhandle. Many are listed below.

Theater and Films:

The cutting-edge performances of new American plays that are the hallmark of the Contemporary American Theater Festival occur in venues around Shepherd University in July of each year, usually starting the weekend after the Fourth of July. Visit their website for more info.

The American Conservation Film Festival features films from a diverse group of conservation filmmakers from around the world and is usually held in late October at venues located in the National Conservation Training Center, Shepherd University and the Opera House. Visit their website for more info.

Arts and Crafts Festivals:

The Mountain Heritage Arts and Crafts Festival is held twice annually, in June and September. About 200 juried craft persons will be selling and demonstrating their wares at this nationally acclaimed festival. Enjoy the many varieties of food that are available along with the best in live Bluegrass entertainment. Visit their website for more info.

During the Over The Mountain Studio Tour, 20 or more professional artists and craft workers – the best of Jefferson County, West Virginia – open their studios and workshops to the public at several different locations on the second weekend of November on a self-guided tour. Visit their website for more info.

Boonesborough Days, held in Boonsboro, MD, in September features Early American art, crafts, antiques, historical demonstrations, and food vendors. Check here for more info.

House and Garden Tours:

The Back Alley Garden Tour and Tea, a weekend tour of the private back gardens of Shepherdstown and a scrumptious tea, is generally held sometime in May. Visit their website for more info.

The Shenandoah-Potomac House and Garden Tour, scheduled for the last full weekend of April, which features docented historic homes open for touring with beautiful floral displays provided by the local garden clubs.  Thomas Shepherd Inn was one of the featured homes in 2016.  Over 700 visitors and a great experience!  Visit the website for more info.

Holiday Celebrations and Parades:

Christmas in Shepherdstown starts every year with the lighting of the town Christmas tree on German Street the Friday after Thanksgiving, and continues into December with Santa’s arrival, a parade, late night hours for shops and a Christmas marketplace. Visit the website for more info.

Shepherdstown has a wonderful May Day celebration, complete with a parade and the traditional dance around the Maypole. Visit the website for more info.

An annual Fourth of July parade followed by a picnic and music at the Morgan’s Grove Park is coordinated by the Shepherdstown Rotary.

An Easter Parade, led by the Easter Bunny, precedes the annual Easter Egg Hunt on the lawn of the Little House on Princess Street.

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History In and Around Shepherdstown, West Virginia:
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Shepherdstown and the surrounding area in West Virginia, Pennsylvania, Virginia and Maryland have many sites that played important roles in Colonial and Civil War era history. Shepherdstown itself is the oldest town in West Virginia and celebrated the 250th anniversary of its founding in 2012, having been officially chartered in 1862.


Entler Hotel and Museum and Historic Shepherdstown

The Museum at the Entler Hotel gives a nice overview of the history of the town; it is open Saturday and Sunday from April to October and during Christmas in Shepherdstown. Visit their website for more info. The Shepherdstown Visitors Center, located on the first floor of the Entler Hotel, has a self-guided walking tour brochure available for visitors (we have a few for borrowing here at the inn).

The Entler hotel is notable for its Revolutionary War history – troops practiced drills here before setting off on the “Beeline March” to join General George Washington in Boston.(

Civil War History – Antietam Battlefield, Harpers Ferry and Gettysburg:

Battle of Shepherdstown

The Battle of Shepherdstown, the most significant Civil War battle fought in what is now West Virginia, occurred at the ford across the Potomac known as Packhorse Ford, which is 1 mile downstream from Shepherdstown. Visit their website for more info.

Antietam National Battlefield

Antietam National Battlefield near Sharpsburg, MD is a quietly moving memorial to the bloodiest day in our nation’s history.  Special events include an annual Fourth of July concert featuring the Maryland Symphony Orchestra followed by an amazing fireworks display.  The first weekend in December marks the lighting of luminaries, one for each of the 23,000 that perished that day. The Visitors Center there features a film about Lincoln’s visit to Antietam shortly after the battle and a ranger-led overview of the battle from the Observation room. Park rangers lead tours of the significant spots near the Visitors Center, like Dunker Church, and a driving tour of the battlefield (on CD or cassette) takes you to Bloody Lane and the Burnside Bridge. Antietam is about 3.5 miles from Shepherdstown, near the small town of Sharpsburg, MD. Visit their website for more info.

Private guides are available and can be booked by contacting the Antietam Museum Store at 301-432-4329.
Now you can tour Antietam National Battlefield by horse and buggy courtesy of Bonnymeed Farm – experience the battleground from a unique perspective (National Park Service approved). Tours on  Saturday and Sunday; weekdays by appointment.  Call 1-304-876-1307 for reservations and information.

Harpers Ferry:

Harpers Ferry, WV has wonderful vistas and a collection of small museums created within original buildings; visiting there is like stepping into the past. Park at the Visitors Center just off Route 340 and take the shuttle into town to visit the John Brown Wax Museum and the historic Arsenal. Living historians are often strolling the town to point out historic sites and answer any questions you might have about what life was like during the Civil War. Harpers Ferry is about 9 miles from Shepherdstown, near the border with Virginia and Maryland. Visit their website for more info.

Ghost Tours and the O’ Be JoyFull musical entertainment tours are top-rated attractions in Harpers Ferry, and loads of fun. Visit their website for more info.

The Court House where John Brown stood trial and was sentenced to hang is in Charles Town, WV, just a few miles from Harpers Ferry and about 9 miles from Shepherdstown.


It is surprisingly easy to visit three significant Civil War battlefields while staying in Shepherdstown, as Gettysburg, PA is only about 75 minutes away. The bloodiest battle in Civil War history (51,000 casualties over three days) and the site of Abraham Lincoln’s most famous speech, the Gettysburg Address, the bustling town in PA stands in contrast to the quiet cornfields of Antietam. Gettysburg is about 70 miles from Shepherdstown in Pennsylvania. Visit their website for more info.

Should you decide to stay overnight in Gettysburg, may we suggest The Doubleday Inn, the only B&B on the battlefield proper.  Visit their website for more info.

Colonial History:

Rumsey Boat House and Rumsey Monument

James Rumsey, a compatriot of George Washington, took the first steamboat out on the Potomac River near Shepherdstown in 1787, well before Robert Fulton’s steamboat took to the water. A half-scale replica of his boat resides in the Rumsey Boat House behind the Entler Museum and a monument to Rumsey stands on the bluffs above the Potomac River just off Mill Street. Visit their website for more info.

Washington Heritage Trail

The Washington family, including George and his brother Charles (for whom Charles Town is named) spent many years in the Eastern Panhandle of West Virginia while it was still part of Virginia. The Washington Heritage Trail, which meanders around all three counties in the Eastern Panhandle, explores the natural and cultural history of 18th century towns, 19th century industrial sites, Washington family homes, springs, rivers and mountain ranges located along its 136 scenic miles. Visit their website for more info.

Guided History Tours

Several excellent tour guides are available for personal guided tours of Antietam, Harpers Ferry, South Mountain and Shepherdstown. Here is the contact information for some of the local guides:

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Outdoor Activities In and Around Shepherdstown, West Virginia:

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You don’t have to worry about the calories you consume while dining out in our wonderful restaurants in Shepherdstown – there are plenty of ways to get some fresh air and burn those meals off while you’re staying at the inn.

Biking and Hiking:


With its connection to the Great Allegheny Passage trail in Cumberland, MD, the C&O Canal Tow Path is 184.5 miles of scenery and adventure ending near Washington, D.C for bicyclists. We welcome cyclists and have a secured bike rack in our back yard (uncovered) for storage; please, no bicycles may be brought into the inn. The access ramp from the Rumsey Bridge to the C&O is less than one mile down Duke Street from the inn. Visit the C&O Canal website for more info.

Shepherdstown Pedal and Paddle at 115 W. German Street rents bicycles as well as kayaks. Guided bicycle historical tours can also be arranged there. Visit the website for more info.

River Riders and River & Trail Outfitters, both near Harpers Ferry, also rent bicycles. Please see their contact info in the Water Sports section below.


The C&O Canal Path, mentioned above, is a relatively flat, shaded hiking surface for easy walking. The Appalachian Trail, near Harpers Ferry, is about nine miles away and offers more challenging hiking. Only about four miles of the Trail lie within the state of West Virginia but it passes within 1/4 mile of the Trail headquarters in Harpers Ferry and continues along the Virginia/West Virginia border for another fifteen miles. Visit the website for more info.

Water Sports:

The Potomac and Shenandoah Rivers offer some of West Virginia’s finest watersports. Everything from fishing and canoeing to kayaking, tubing and whitewater rafting are available. River Riders in Harpers Ferry provides outfitting services for all of the above sports, as well as bicycle rentals. Visit the website for more info.

River & Trail Outfitters, also in Harpers Ferry, offers guided whitewater rafting, tubing, kayaking, and canoeing. They also coordinate climbing, team-building and hiking trips. Visit the website for more info.


Golfers who stay at the inn can play at Locust Hill Golf Course in Charles Town. Locust Hill has been rated #5 by Golf Week Magazine for best public access course. Please visit their website for more information.

Horseback Riding:

Guided horseback rides are available at Elk Mountain Trails near Harpers Ferry, about 9 miles away. Visit the website for more info.

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Shopping In and Around Shepherdstown, West Virginia:
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It’s easy to while away the better part of a day browsing the delightful shops of Shepherdstown, all within walking distance of the Inn.

German Street and Princess Street:

German Street is lined with one-of-a-kind shops offering something for every taste. None are chain stores and all are locally-owned small businesses. Visit the Shepherdstown Visitors Center website for a more comprehensive listing of the shops.

Farmers Market and Orchards:

The Shepherdstown Farmers Market, opening Easter weekend and closing around the Christmas holidays, is located behind the library on King Street, which is closed to traffic on Sunday mornings during the season. Follow the market on Facebook for announcements about weekly specials and photos of produce and flowers.


Outlet Shopping:

If you are looking for bargains, the Prime Outlet Mall is just about 20 minutes away, near Hagerstown, MD. Visit the website for more info.

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Spa Services In and Around Shepherdstown, West Virginia:
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Several small businesses offer spa services in and around Shepherdstown.


Jala Yoga at 117 W. German St.  offers daily yoga classes.  For more information or to schedule a class visit them online or call them at 401-440-0279.

Skin Care, Facials and Waxing:

Off Mane Street at 109 S. Princess Street in Shepherdstown does manicures, pedicures, ear candling and waxing. Visit the website or call them directly, 304-876-6060, for more information.

Soul of Skincare and Wellness at 121 W. German St. specializes in organic skin care, facials, waxing and integrated massage.  They are open by appointment only.  Book online or call or text them at 240-818-9327.


Aanandha Health and Wellness at 217 South Duke Street, #104, offers massage services just a 2 block walk from the inn. Visit their website  or call directly at (304)362-3009.

Full-Service Spa:

Serenity Day Spa offers a full array of spa services and is located in Martinsburg, a 15-minute drive from the inn. Visit their website or call them directly (304-263-4200) for more info.

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Wineries near Shepherdstown, West Virginia:
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There are several wineries within an hour’s drive of Shepherdstown, most in the Loudoun Valley of northern Virginia. Tastings are available and some have event weekends with food and music.

Loudoun Valley and northern Virginia Vineyards:

Breaux Vineyards, voted the best winery in Virginia the last three years, has beautiful terraces overlooking their acreages of grapes. They have several events throughout the year, including a Cajun Festival and wine-pairing dinners for Valentine’s Day. Visit the website for more info.

Hillsborough Vineyards has beautiful stone buildings among landscaped gardens and offers wedding services in a special setting. Visit the website for more info.

Notaviva Vineyards has a music loft and live music performances every weekend. Visit the website for more info.

Doukenie Winery offers frequent dinner events and cooking classes, along with live music performances. Visit the website for more info.

There are at least a dozen more wineries and vineyards in the northern Virginia area just across the West Virginia border. Visit the Virginia wine website for more info. Choose the Northern Virginia region option for a complete list of tasting rooms around Purcellville, Hillsborough and Leesburg.

Maryland Wineries:

Knob Hall Winery in Western Maryland is near Clear Spring, about 20 miles from Shepherdstown. The tasting room is open on weekends only, and there are often music events. Visit the website for more info.

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