Day Trips from Winchester
← All Winchester day tripsDay Trips from Winchester: Wineries & Vineyards
Discover the best wineries and vineyards within driving distance of Winchester, VA. From intimate tasting rooms to sprawling estate vineyards, these destinations make for a perfect day trip or weekend wine getaway. Real drive times, ratings, and booking links included.
12 wineries near Winchester
Vino Virginia Wine Tours
1900 S Eads St, Arlington
Just 1 hr 23 min from Winchester, rated 5.0 stars by 200 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Monticello Wine Tour and Coach Co
Charlottesville, VA 22902
Just 2 hrs 4 min from Winchester, rated 5.0 stars by 173 visitors, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
Spirited Tours
Washington, DC 20004
Just 1 hr 29 min from Winchester, rated 5.0 stars by 205 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Blue Ridge Wine Excursions
Charlottesville, VA 22911
Just 2 hrs 6 min from Winchester, rated 5.0 stars by 554 visitors, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
Carriage House Wineworks
Waterford, VA 20197
Just 47 min from Winchester, rated 4.9 stars, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
DiVine Wine Tours of Virginia
Dulles, VA 20166
Just 58 min from Winchester, rated 4.9 stars by 171 visitors, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
Two Lions Vineyards
Upper Marlboro, MD 20772
Just 1 hr 57 min from Winchester, rated 4.8 stars by 290 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Rocklands Farm Winery
Poolesville, MD 20837
Just 1 hr 27 min from Winchester, rated 4.7 stars by 571 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Old Westminster Winery
Westminster, MD 21157
Just 1 hr 34 min from Winchester, rated 4.7 stars by 1,321 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Hidden Hills Farm and Vineyard
Frederick, MD 21701
Just 1 hr 15 min from Winchester, rated 4.7 stars by 172 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
King Family Vineyards
Crozet, VA 22932
Just 1 hr 51 min from Winchester, rated 4.7 stars by 839 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Cave Ridge Vineyard
Mt Jackson, VA 22842
Just 51 min from Winchester, rated 4.7 stars by 240 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Frequently Asked Questions About Wineries Day Trips from Winchester
What are the best wineries near Winchester, VA?
The best wineries near Winchester include award-winning vineyards, tasting rooms, and estate wineries all within a few hours' drive. Check the destination cards above for ratings, drive times, and direct booking links.
Are there wine tours near Winchester?
Yes. Many wineries near Winchester offer guided tastings and tours. Use the "Book Activities" button on any card to find wine tour packages through Viator and GetYourGuide, which often include transportation and multi-winery stops.
How far are the closest wineries from Winchester?
The closest wineries to Winchester are typically 45 minutes to 2 hours away, making them ideal for a day trip. Some regions farther out (2-3 hours) are worth an overnight stay for a full wine weekend.
What is the best time to visit wineries near Winchester?
Fall harvest season (September-October) is peak time for wineries, with grape picking and crush events. Spring and summer offer beautiful vineyard scenery. Most tasting rooms are open year-round, and winter visits mean smaller crowds and more personal attention.
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