- 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 131-140 of
535
24.0 Miles
91%
187 votes
37251C East Richardson Lane, Purcellville, VA 20132
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Powering its distillery with solar energy, Catoctin Creek Distillery produces a variety of spirits in D.C's wine country. In the tasting room, visitors can sample from a selection of whiskey, brandy, and cocktails.
24.1 Miles
The owners of Glen Manor Vineyards attempt to make each trip educational in nature. They offer tours that cover make winemaking and vineyard growing techniques along with frequent tastings throughout the day.
24.1 Miles
Originally named 29 vines, the Above Ground Winery offers Exit Strategy Chardonnay, Sweet Rebecca Red, and Wild River Red wines. The downtown tasting room was closed in 2013, but they host samplings at various farmer's markets in Virginia.
24.1 Miles
89%
19 votes
12944 Harpers Ferry Road, Purcellville, VA 20132
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Known for buttery Chardonnays and spicy Cab Francs, Two Twisted Posts Winery offers these wines plus more, for tasting and purchase. A visit may include a vineyard tour, croquet on the lawn, or a secluded picnic in the woods.
24.1 Miles
Located in a man-made cave for a unique feel and reduced carbon footprint, the Maggie Malick Wine Cave is a winery and wine seller. The winery welcomes visitors, and serves food as well as wine.
24.2 Miles
100%
11 votes
250 S. Nursery Ave., Purcellville, VA 20132
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Located within the Bush Tabernacle building, the Purcellville Skating Rink is a non-profit roller skating rink that offers free skate rentals included in the price of admission. Visitors commonly enjoy attending public skating sessions or birthday parties at the rink.
24.2 Miles
93%
70 votes
Harpers Ferry Center, Harpers Ferry, WV 25425
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The Appalachian National Scenic Trail is a 2,184-mile long public footpath that was constructed by volunteers over the course of 16 years. The Appalachian Conservatory Trail was organized to help protect the trail.
24.2 Miles
100%
2 votes
Roosevelt Island DC to Allegheny Highlands PA, Harpers Ferry, WV 25425
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Potomac Heritage Trail offers visitors outdoor activities such as hiking, fishing, biking, rafting, and boating. The trail goes through forests, has rocky terrain, and passes by streams. There are also views of the Potomac River.
24.3 Miles
Fireman's Field is a 13-acre park that includes two baseball fields with the main one selected as the site of the Babe Ruth League World Series in 2013. The park features a skating rink and hosts numerous events and concerts.
24.3 Miles
Cacapon State park contains 6,115 acres. The park has 20 miles of hiking trails, trails for horseback riding, fishing in the Cacapon River, golf course, a 250-person conference center, cabins, and an inn.