- TripBuzz discovered 83 different types of activities for couples in the Winchester area, including Movie Theaters (like Alamo Drafthouse Cinema), Historic Sites (like Stonewall Jackson's Headquarters), Theaters (like Winchester Little Theatre) and Art Museum (like Glen Burnie Historic House & Gardens), and much more.
- We discovered a total of 120 date ideas in or near Winchester, Virginia, including 100 fun or romantic activities in nearby cities within 25 miles like Martinsburg, Purcellville, Front Royal and Harpers Ferry.
Showing 131-140 of
425
26.6 Miles
Founded in 1969, the Middleburg Tennis Club is a members-only recreation site with over 10 acres of courts and facilities. Tennis lessons and camps are offered, along with a swimming pool and full size fitness center.
26.8 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.
26.8 Miles
98%
43 votes
500 N Pendleton Street, Middleburg, VA 20117
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Guests can coast along the forest canopy at Salamander Tree Top Zip Tour. Packages include zip lining on the 20 acres of land, a rappelling adventure, survival 101, and a leadership odyssey.
27.3 Miles
Lovers of equestrian, angling, and field sports can learn more about their passion at the National Sporting Library. Guests can explore the research facility, manuscripts, works of art, and a free library.
27.3 Miles
100%
2 votes
102 The Plains Road, Middleburg, VA 20117
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Home to over 26,000 books, National Sporting Library & Fine Arts Museum is open to the general public for research or personal use. Visitors can peruse books specialized in sporting and animal books from year 1500 to 2000.
27.4 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.
27.4 Miles
Wine tastings at The Boxwood Winery are the main draw to the site since there are no tours of the vineyards or the wine cellar itself. The location also has a wine bar that serves Boxwood wines and other wines from around the world.
27.4 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.
27.4 Miles
Spread over 112 acres, Glenwood Park is actually an equine venue. The land was originally donated to the city in 1963 and currently holds races, charitable events, and a pony club competition.
27.4 Miles
Enjoy the beauty of a 56 acre vineyard and sample fine De Chaunac, Seyval Blanc and Marchel Foch wines while enjoying a wine tasting tour of Smith family owned and operated Meredyth Vineyards in the heart of Virginia's wine country.