Things to Do in Winchester, VA

  • 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
  • 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 171-180 of 535
27.4 Miles
37% 19 votes
Winery/Vineyard 16 E Washington St, Middleburg, VA 20117 MoreLess Info
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
44% 71 votes
Winery/Vineyard 2042 Burrland Rd, Middleburg, VA 20117 MoreLess Info
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
Walking Tours Pink Box, Middleburg Visitors Center, Middleburg, VA 20117 MoreLess Info
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
100% 3 votes
Parks Route 626, Middleburg, VA 20117 MoreLess Info
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
100% 1 votes
Winery/Vineyard Route 626, Middleburg, VA 20118 MoreLess Info
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.
27.4 Miles
64% 14 votes
Parks 2845 North Marcey Road, Middleburg, VA 22207 MoreLess Info
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.
27.4 Miles
67% 3 votes
Art Gallery 7 West Washington Street, Middleburg, VA 20117 MoreLess Info
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.
27.5 Miles
86% 7 votes
Historic Sites 2406 Chestnut Grove Road, Sharpsburg, MD 21782 MoreLess Info
Now a National Historic Landmark, The Kennedy Farm was built in the 1850s by Dr. Robert F. Kennedy. It was once rented by John Brown, of the Harper's Ferry Raid. The building has been thoroughly restored.
28.2 Miles
58% 38 votes
Winery/Vineyard 38906 Mount Gilead Road, Leesburg, VA MoreLess Info
Tastings are offered at the Willowcroft Farm Vineyards on-site tasting room. The venue is open to the general public on Thursdays through Sundays, and specialty chocolate and wine pairings are available.
28.8 Miles
84% 62 votes
Winery/Vineyard 23595 Winery Lane, Middleburg, VA MoreLess Info
Set in the Blue Ridge Mountains, Greenhill Vineyards produces several varietals from its own Virginia grapes. The winery offers a tasting room, open daily, and a variety of food and picnicking options.
Showing 171-180 of 535
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