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Upperville Events and Things to do in Upperville, VA

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Almost full
Hoedown 2026
Friday at 5:00 PM
Virginia · 18297 Yellow Schoolhouse Rd
Almost full
Hoedown 2026
Friday at 5:00 PM
Virginia · 18297 Yellow Schoolhouse Rd
Next Stop Comedy at Three Fox Vineyards and Brewery! - Delaplane, VA
Sat, Nov 21, 7:00 PM + 4 more
Virginia · Three Fox Vineyards & Farm Brewery
Next Stop Comedy at Three Fox Vineyards and Brewery! - Delaplane, VA
Sat, Nov 21, 7:00 PM + 4 more
Virginia · Three Fox Vineyards & Farm Brewery
Selling fast
Pours to Explore Tasting Series: Sauvignon Blanc & Cabernet Franc
Sat, Nov 14, 6:00 PM
Virginia · Bluemont Vineyard
Selling fast
Pours to Explore Tasting Series: Sauvignon Blanc & Cabernet Franc
Sat, Nov 14, 6:00 PM
Virginia · Bluemont Vineyard
Spaghetti Dinner Fundraiser Supporting the Nelson Family
Tue, Oct 27, 5:30 PM
Purcellville · American Legion Post 293
Spaghetti Dinner Fundraiser Supporting the Nelson Family
Tue, Oct 27, 5:30 PM
Purcellville · American Legion Post 293
Charm City Junction
Sun, Nov 15, 5:00 PM
The Plains · Grace Episcopal Church
Charm City Junction
Sun, Nov 15, 5:00 PM
The Plains · Grace Episcopal Church
3rd Annual Great Meadow Veterans Cup: Polo with Purpose
Sun, Nov 8, 11:00 AM
Virginia · Great Meadow
3rd Annual Great Meadow Veterans Cup: Polo with Purpose
Sun, Nov 8, 11:00 AM
Virginia · Great Meadow
Sales end soon
Lake Store of Horror
Saturday at 6:00 PM
Virginia · E.E. Lake General Store
Sales end soon
Lake Store of Horror
Saturday at 6:00 PM
Virginia · E.E. Lake General Store
Sunday Mahjong Open Play at Three Fox Vineyards and Brewery
Sun, Nov 8, 12:00 PM
Virginia · Three Fox Vineyards & Farm Brewery
Sunday Mahjong Open Play at Three Fox Vineyards and Brewery
Sun, Nov 8, 12:00 PM
Virginia · Three Fox Vineyards & Farm Brewery
Almost full
Mahjong at the Vineyard | Winery at La Grange
Saturday at 1:00 PM
Virginia · The Winery at La Grange
Almost full
Mahjong at the Vineyard | Winery at La Grange
Saturday at 1:00 PM
Virginia · The Winery at La Grange
Lail Vineyards Wine Dinner
Fri, Oct 30, 6:00 PM
Virginia · The Buttery
Lail Vineyards Wine Dinner
Fri, Oct 30, 6:00 PM
Virginia · The Buttery
Project Knapsack invites you to A Seat At The Table
Sat, Nov 21, 4:00 PM
Virginia · Black Oak Farm
Project Knapsack invites you to A Seat At The Table
Sat, Nov 21, 4:00 PM
Virginia · Black Oak Farm
Almost full
Wicked Fun Mahjong Open Play at Great Mane Brewery- Haymarket
Mon, Oct 26, 6:30 PM
Haymarket · Great Mane Brewery
Almost full
Wicked Fun Mahjong Open Play at Great Mane Brewery- Haymarket
Mon, Oct 26, 6:30 PM
Haymarket · Great Mane Brewery
2026-2027 Grace Church Concert Series Angel Donations
Sun, May 16, 5:00 PM
The Plains · Grace Episcopal Church
2026-2027 Grace Church Concert Series Angel Donations
Sun, May 16, 5:00 PM
The Plains · Grace Episcopal Church
Selling fast
November Bird Walk
Fri, Nov 6, 8:00 AM
Virginia · Blandy Experimental Farm/State Arboretum of Virginia
Selling fast
November Bird Walk
Fri, Nov 6, 8:00 AM
Virginia · Blandy Experimental Farm/State Arboretum of Virginia
Audley Farm Wine Dinner
Thu, Nov 19, 6:00 PM
Virginia · Audley Farm
Audley Farm Wine Dinner
Thu, Nov 19, 6:00 PM
Virginia · Audley Farm
Halloween at Hogwarts
Sat, Oct 31, 3:00 PM
Ashburn · Stone Bridge High School
Halloween at Hogwarts
Sat, Oct 31, 3:00 PM
Ashburn · Stone Bridge High School
AI for Realtors 2.0: Build Your Own AI Team
Thu, Nov 5, 9:30 AM
Brambleton · The Barn at Brambleton
AI for Realtors 2.0: Build Your Own AI Team
Thu, Nov 5, 9:30 AM
Brambleton · The Barn at Brambleton
Approach to Inflammation Health & Wellness Event
Tue, Oct 27, 5:00 PM
Leesburg · Leesburg Volunteer Fire Company Banquet Hall
Approach to Inflammation Health & Wellness Event
Tue, Oct 27, 5:00 PM
Leesburg · Leesburg Volunteer Fire Company Banquet Hall
Selling fast
Haunted Nights at Twin Oaks: Ghost Tour & Wine Tasting
Friday at 6:30 PM + 3 more
Virginia · Twin Oaks Tavern Winery
Selling fast
Haunted Nights at Twin Oaks: Ghost Tour & Wine Tasting
Friday at 6:30 PM + 3 more
Virginia · Twin Oaks Tavern Winery
Christmas In Middleburg Parking
Sat, Dec 5, 8:00 AM
Virginia · Mt.Defiance Cidery and Distillery
Christmas In Middleburg Parking
Sat, Dec 5, 8:00 AM
Virginia · Mt.Defiance Cidery and Distillery

1 of 500

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