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Winery Events and Things to do in Winchester, VA

Pure Barre Ashburn Village Pop-Up Class
Sun, Jun 28, 10:00 AM
Leesburg · Fleetwood Farm Winery, Evergreen Mills Rd, Leesburg, VA, USA
Pure Barre Ashburn Village Pop-Up Class
Sun, Jun 28, 10:00 AM
Leesburg · Fleetwood Farm Winery, Evergreen Mills Rd, Leesburg, VA, USA
Pours to Explore Tasting Series: Rosé, Petit Manseng & Petit Verdot
Sat, Jun 13, 6:00 PM
Middleburg · Cana Vineyards and Winery of Middleburg
Pours to Explore Tasting Series: Rosé, Petit Manseng & Petit Verdot
Sat, Jun 13, 6:00 PM
Middleburg · Cana Vineyards and Winery of Middleburg
Yoga at the Vineyard
Sun, Jun 14, 10:00 AM
Purcellville · Kalero Vineyard
Yoga at the Vineyard
Sun, Jun 14, 10:00 AM
Purcellville · Kalero Vineyard
Delta Spur - Country Music Favorites
Sat, Jun 20, 6:00 PM
Leesburg · Tarara Winery
Delta Spur - Country Music Favorites
Sat, Jun 20, 6:00 PM
Leesburg · Tarara Winery
Book Bedazzling at Springfield Manor
Sat, Jun 20, 12:00 PM
Thurmont · Springfield Manor Winery & Distillery
Book Bedazzling at Springfield Manor
Sat, Jun 20, 12:00 PM
Thurmont · Springfield Manor Winery & Distillery
Lebanese Wine Pairing Dinner at Byblos Winchester
Sun, Jul 12, 6:00 PM
Winchester · Byblos Winchester
Lebanese Wine Pairing Dinner at Byblos Winchester
Sun, Jul 12, 6:00 PM
Winchester · Byblos Winchester
Ryan Jewel's 4th Album Release Party
Sat, Jun 27, 5:00 PM
Front Royal · Reitano Vineyards
Ryan Jewel's 4th Album Release Party
Sat, Jun 27, 5:00 PM
Front Royal · Reitano Vineyards
Sales end soon
Proudly Poured: Pride in the Vines Kick Off Drag Brunch
Sunday at 12:00 PM
Middleburg · Mt. Defiance Cidery & Distillery
Sales end soon
Proudly Poured: Pride in the Vines Kick Off Drag Brunch
Sunday at 12:00 PM
Middleburg · Mt. Defiance Cidery & Distillery
Sales end soon
Weekly Live Trivia Nights at Nokesville Winery - Nokesville
Thursday at 7:00 PM + 40 more
Nokesville · Nokesville Winery
Sales end soon
Weekly Live Trivia Nights at Nokesville Winery - Nokesville
Thursday at 7:00 PM + 40 more
Nokesville · Nokesville Winery
Just added
The Pop Chicks in the Pavilion
Fri, Jun 19, 7:00 PM
Lovettsville · 41255 Annas Ln
Just added
The Pop Chicks in the Pavilion
Fri, Jun 19, 7:00 PM
Lovettsville · 41255 Annas Ln
Goat Yoga at Springfield Manor 7/18
Sat, Jul 18, 10:00 AM
Thurmont · Springfield Manor Winery & Distillery
Goat Yoga at Springfield Manor 7/18
Sat, Jul 18, 10:00 AM
Thurmont · Springfield Manor Winery & Distillery
Plein Air paint and sip
Sat, Jun 20, 12:00 PM
Hillsboro · Doukénie Winery
Plein Air paint and sip
Sat, Jun 20, 12:00 PM
Hillsboro · Doukénie Winery
LoCo Fest 2026
Sun, Sep 6, 12:00 PM
Hillsboro · 868 Estate Vineyards
LoCo Fest 2026
Sun, Sep 6, 12:00 PM
Hillsboro · 868 Estate Vineyards
Stand Up Comedy Night at Lost Rhino Brewing
Fri, Jul 10, 7:30 PM
Ashburn · Lost Rhino Brewing Company
Stand Up Comedy Night at Lost Rhino Brewing
Fri, Jul 10, 7:30 PM
Ashburn · Lost Rhino Brewing Company
Sales end soon
Live Music with Wayne Snow
Sunday at 2:00 PM
Purcellville · Breaux Vineyards
Sales end soon
Live Music with Wayne Snow
Sunday at 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Chris Compton
Sun, Jun 14, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Chris Compton
Sun, Jun 14, 2:00 PM
Purcellville · Breaux Vineyards
Sales end soon
White Ford Bronco – The Ultimate ‘90s Party
Saturday at 6:00 PM
Leesburg · Tarara Winery
Sales end soon
White Ford Bronco – The Ultimate ‘90s Party
Saturday at 6:00 PM
Leesburg · Tarara Winery
Live Music with Brian Harris
Sat, Jun 20, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Brian Harris
Sat, Jun 20, 2:00 PM
Purcellville · Breaux Vineyards
Sip & Stretch on the River at Whites Ferry Brewery
Sat, Jun 20, 10:30 AM
Leesburg · Whites Ferry Brewery
Sip & Stretch on the River at Whites Ferry Brewery
Sat, Jun 20, 10:30 AM
Leesburg · Whites Ferry Brewery
Public Knitoxication - 2026
Sat, Jun 20, 12:00 PM
Leesburg · Fabbioli Cellars
Public Knitoxication - 2026
Sat, Jun 20, 12:00 PM
Leesburg · Fabbioli Cellars

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