- Our list of the best things to do in Shepherdstown, West Virginia, features the top 185 nearby activities — including 68 great attractions with user approval ratings of 90% or more!
- Shepherdstown, WV has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Entertainment & Shows, Museums & Galleries, and Sights & Landmarks.
- The results below include the top 7 things to do within the city of Shepherdstown, WV , followed by 179 popular activities in nearby cities, including Hagerstown, Frederick, Purcellville, Martinsburg, Harpers Ferry, Berryville, Leesburg, Charles Town, Sharpsburg, Thurmont, Winchester, Berkeley Springs, Middletown, Boonsboro, Knoxville and Lovettsville
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42.9 Miles
Visitors can choose from a selection of red and white wines to sample in the tasting room at Serpent Ridge Vineyard. The vineyard offers scenic views of the native trees that surround it.
43.2 Miles
The historic Glenview Mansion is a home built in 1926 that is listed on the National Register of Historic Places. The mansion sits on 153-acres of land and hosts a number of public and private events during the year.
43.3 Miles
Adjacent to both the Glenview Mansion and the F. Scott Fitzgerald Theater, Civic Center Park is spread over 153 acres with a large section of formal gardens. The park also offers outdoor fitness equipment, a nature trail, art in public spaces, a children's playground, and a wildlife sanctuary.
43.5 Miles
The 5-acre Tallyho Swim & Tennis Club is a recreational sports club that features a heated 6-lane swimming pool, a regulation beach volleyball court, and two lighted tennis courts. The club also provides wireless Internet.
43.7 Miles
Billy Goat Trail is a popular hiking trail located on and around the Potomac River and offers both a strenous rocky terrain as well as flat ground to suit hikers with varying skills.
43.7 Miles
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3460 Olney Laytonsville Road, Olney, MD 20832
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Established for the advancement of young dancers, the Olney Childrens Ballet Theater offers a venue for dancers to learn and perform in a live theater setting. The theater produces live shows and offers auditions for interested young dancers.
43.9 Miles
The Olney Boys & Girls Club is a community center that provides after school sports programs for children. Established in 1969, the club offers a variety of sports including basketball, baseball, softball, soccer, football, field hockey, and lacrosse.
44.0 Miles
Ellanor C. Lawrence Park serves as a wildlife preservation area. Visitors can hike, picnic, and learn more about the area in the Walney Visitor Center's refurbished 1780's farmhouse.
44.1 Miles
Visitors to the Chantilly area can gain knowledge of the area and enjoy outdoor recreation at the Walney Visitor Center. The surrounding trails provide scenic hikes, while the indoor nature center provides entertainment for the younger crowd.
44.1 Miles
18127 Towne Center Drive, Olney, MD 20832
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Situated in the Fair Hills Shopping Center, the Winery at Olney imports raw grape products for the creation of their wines from renowned grape growing areas across the globe. Guests can also make their own custom wine batch of 28 to 30 bottles.