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September Events and Things to do in Winchester, VA

Next Stop Comedy at Three Fox Vineyards and Brewery! - Delaplane, VA
Friday at 8:00 PM
Virginia · Three Fox Vineyards & Farm Brewery
Next Stop Comedy at Three Fox Vineyards and Brewery! - Delaplane, VA
Friday at 8:00 PM
Virginia · Three Fox Vineyards & Farm Brewery
Bad Animals - The Heart Tribute - with The Andy Hawk Trio
Sat, Sep 12, 6:00 PM
Virginia · Tarara Winery
Bad Animals - The Heart Tribute - with The Andy Hawk Trio
Sat, Sep 12, 6:00 PM
Virginia · Tarara Winery
IPT Sunset Polo Charity Series 2026
Sat, Sep 19, 4:00 PM
Virginia · 41580 Sunday Morning Ln
IPT Sunset Polo Charity Series 2026
Sat, Sep 19, 4:00 PM
Virginia · 41580 Sunday Morning Ln
Women's CEO Summit Intensive 2026
Fri, Sep 25, 8:00 AM
Brambleton · The Barn at Brambleton
Women's CEO Summit Intensive 2026
Fri, Sep 25, 8:00 AM
Brambleton · The Barn at Brambleton
Sunset Yoga at the Vineyard
Fri, Sep 18, 7:00 PM
Virginia · Kalero Vineyard
Sunset Yoga at the Vineyard
Fri, Sep 18, 7:00 PM
Virginia · Kalero Vineyard
Oatlands Garden Soirée
Sun, Sep 20, 3:00 PM
Virginia · Oatlands Historic House & Gardens
Oatlands Garden Soirée
Sun, Sep 20, 3:00 PM
Virginia · Oatlands Historic House & Gardens
Sunday Morning Yoga & Sound
Sun, Sep 27, 10:00 AM
Virginia · Kalero Vineyard
Sunday Morning Yoga & Sound
Sun, Sep 27, 10:00 AM
Virginia · Kalero Vineyard
HIGH NOON - The East Coast's Premier Tribute to Southern Rock
Sat, Sep 19, 6:00 PM
Virginia · Tarara Winery
HIGH NOON - The East Coast's Premier Tribute to Southern Rock
Sat, Sep 19, 6:00 PM
Virginia · Tarara Winery
Wild Game & Beer Pairing Dinner
Tue, Sep 15, 6:30 PM
Virginia · 36577 Heskett Ln
Wild Game & Beer Pairing Dinner
Tue, Sep 15, 6:30 PM
Virginia · 36577 Heskett Ln
Family Volunteering Series: Plant Trees with Mini Changemakers
Sun, Sep 27, 10:00 AM
Maryland · 4855 Broad Run Rd
Family Volunteering Series: Plant Trees with Mini Changemakers
Sun, Sep 27, 10:00 AM
Maryland · 4855 Broad Run Rd
Trivia Night at Box Office Brewery
Tuesday at 6:30 PM + 3 more
Strasburg Junction · Box Office Brewery
Trivia Night at Box Office Brewery
Tuesday at 6:30 PM + 3 more
Strasburg Junction · Box Office Brewery
Naghma Live Concert Virginia US
Sat, Sep 12, 5:00 PM
Lansdowne · 18980 Upper Belmont Pl
Naghma Live Concert Virginia US
Sat, Sep 12, 5:00 PM
Lansdowne · 18980 Upper Belmont Pl
Barnyard Buddies
Saturday at 1:00 PM + 2 more
Virginia · Sky Meadows State Park
Barnyard Buddies
Saturday at 1:00 PM + 2 more
Virginia · Sky Meadows State Park
Critter Chow
Friday at 2:00 PM + 2 more
Virginia · Sky Meadows State Park
Critter Chow
Friday at 2:00 PM + 2 more
Virginia · Sky Meadows State Park
Create Your LSO Season Subscription Package
Sat, Sep 19, 7:30 PM
Brambleton · Independence High School
Create Your LSO Season Subscription Package
Sat, Sep 19, 7:30 PM
Brambleton · Independence High School
Doggy Noses & Yoga Poses at Winery at La Grange
Sun, Sep 20, 11:00 AM
Virginia · The Winery at La Grange
Doggy Noses & Yoga Poses at Winery at La Grange
Sun, Sep 20, 11:00 AM
Virginia · The Winery at La Grange
Soothing Sound Bath & Tea Ceremony with Shauna Whisenton
Sun, Sep 27, 10:00 AM
Maryland · Fox Haven Organic Farm & Learning Center
Soothing Sound Bath & Tea Ceremony with Shauna Whisenton
Sun, Sep 27, 10:00 AM
Maryland · Fox Haven Organic Farm & Learning Center
Wine Tasting & Pouring Paint on Pumpkins
Fri, Sep 25, 6:30 PM
Leesburg · The King Street Experience
Wine Tasting & Pouring Paint on Pumpkins
Fri, Sep 25, 6:30 PM
Leesburg · The King Street Experience
Vendor Sign Up For Purcellville Farmers Market
Saturday at 9:00 AM + 2 more
Purcellville · Nostalgia Boutique
Vendor Sign Up For Purcellville Farmers Market
Saturday at 9:00 AM + 2 more
Purcellville · Nostalgia Boutique
September Cash Bingo
Sun, Sep 13, 12:00 PM
Hancock · Hancock American Legion Post 26
September Cash Bingo
Sun, Sep 13, 12:00 PM
Hancock · Hancock American Legion Post 26

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