- Our list of the best things to do in Winchester, Virginia, features the top 153 nearby activities — including 61 great attractions with user approval ratings of 90% or more!
- Winchester, VA has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Museums & Galleries, Sights & Landmarks, and Entertainment & Shows.
- The results below include the top 26 things to do within the city of Winchester, VA , followed by 126 popular activities in nearby cities, including Martinsburg, Purcellville, Front Royal, Harpers Ferry, Strasburg, Berryville, Delaplane, Charles Town, Berkeley Springs, Middletown, Strasburg and Middleburg
Showing 141-150 of
535
24.3 Miles
Visitors can enjoy a diverse collection white, red, and dessert wines at Doukenie Winery. The winery hosts tastings, tours, and other special events and has won numerous awards for their wines.
24.3 Miles
The Virginia Wine Country Half Marathon is a wine-themed run, with a wine stop at midpoint and the Wine & Music Festival held at a winery at the end. The course passes through vineyards, farms, ranches and estates.
24.5 Miles
Nestled in Virginia's Piedmont, Miracle Valley Vineyard attracts wine lovers with its scenic beauty. Guests can partake in wine tasting guided by expert staff, stroll the grounds or take in surrounding views from the gazebo.
24.5 Miles
From Shakespeare to Broadway classics, Run Rabbit Run Theatre showcases the talent of community performers in its yearly productions. The theater also organizes arts education programs by offering acting classes.
24.6 Miles
Running along an old canal, Armory Canal Trail offers placards with historical information and views of old factories and ruins. The trail can be used for hiking and has wildlife like birds, fish and turtles that can be seen.
24.6 Miles
100%
3 votes
Appalachian Trail Conservancy Headquarters, 799 Washington Street, Harpers Ferry, WV 25425
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The Appalachian Trail is a famous, 2000 mile trail that allows hikers to explore the Appalachia region of New England. The trail is strung with a variety of lakes, streams, forests, stone structures, and wildlife.
24.7 Miles
94%
1298 votes
171 Shoreline Drive, Harpers Ferry, WV 25425
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Costumed park staff and volunteers present historical vignettes throughout Harpers Ferry National Park on some days, while on other days, visitors can take classes to learn to knit, raise a garden, and bake bread. Visitors can also hike and fish at the park.
24.8 Miles
Open year round for tastings, the Cobbler Mountain Cellars serves many visitors in the region. They actually do hold events during the warmer months though, including special dinners and tastings.
24.8 Miles
Overlooking the Potomac River, Jefferson Rock is a rock formation along the Appalachian trail. The rock offers stunning panoramic views of the river and surrounding wilderness areas, and is accessible by hiking.
25.0 Miles
3623 Grove Lane, Delaplane, VA 20144
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Exploration and relaxation are combined at the Barrel Oak Winery which encourages tours of the grounds and enjoyment of the site in addition to the wine. While they do offer tastings on a regular basis, they also provide events like concerts and bonfires.