- 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
Showing 261-270 of
703
31.9 Miles
The historic farm of Sky Meadows forms the basis of the Sky Meadows State Park which is spread over 1,864 acres. Common activities include touring the historic home, hiking, picnicking, fishing, biking, and participating in the frequent nature and history programs.
32.0 Miles
The first commercial vineyard in Virginia was the Piedmont Vineyards & Winery. The small and homey winery remains a favorite stop along the Virginia wine trail and holds regular tastings that involve knowledgeable servers.
32.0 Miles
64%
14 votes
2845 North Marcey Road, Middleburg, VA 22207
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Located along the Potomac River, Potomac Overlook Regional Park is situated on 70 acres of wooded terrain. The park provides hiking trails, a picnic area, an educational garden and a nature center with exhibits and live animals.
32.1 Miles
37%
19 votes
16 E Washington St, Middleburg, VA 20117
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Rather than a classic winery aesthetic, The Boxwood Tasting Room, Wine Bar, & Shop embraces modern architecture and design through the wide use of stainless metal. Tastings are held throughout the week and wines can be purchased at the shop with the wine bar portion open in the evenings.
32.1 Miles
With 8 screens for the newest released movies, Alamo Cinema Drafthouse is a local favorite. The theater has taken every precaution to create a comfortable atmosphere, including removing the traditional front row of seats so there are no bad seats in the house.
32.1 Miles
Located next to Beaverdam Reservoir, Edgar Tillet Memorial Park measures 51 acres and provides views of the reservoir. The park features two softball and two baseball fields as well as picnic areas.
32.1 Miles
100%
9 votes
Pink Box, Middleburg Visitors Center, Middleburg, VA 20117
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With Destination Middleburg: A Walking Tour Into the Past, visitors can learn about the history of the town and its role in the Civil War. The tour takes visitors through the important landmarks and historical sites of the town.
32.1 Miles
A venue for shows and a variety of equestrian competitions, Fox Chase Farm specializes in jumper entertainment and performance. The farm is also a popular choice for weddings and other special events.
32.1 Miles
Opened in 1995, The Byrne Gallery is a local art gallery featuring a number of works and services available. In addition to displaying a variety of exhibitions, the gallery also offers custom framing, appraisal, and art installation for its customers.
32.2 Miles
57%
74 votes
38600 John Mosby Highway, Middleburg, VA 20117
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With an attached porch and patio the tasting room of Cana Vineyards & Winery allows guests to both taste their wines and view the vineyards. Light fare such as cheeses, breads, meats, and spreads are also available within the tasting room.