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Upperville Featured Events
Arts And Entertainment

Art of the Piedmont

Friday, Mar 28, 2025 from 6:00pm to 8:00pm
Middleburg, VA
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Nicholas Jamerson

Friday, Mar 28, 2025 at 7:00pm
The Monument
Winchester, VA
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Nicholas Jamerson

Almost Queen and Devil’s Smile

Friday, Mar 28, 2025 at 8:00pm
Backseat Events
Winchester, VA
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Almost Queen and Devil’s Smile

Live Music with Zach Jones

Saturday, Mar 29, 2025 from 1:30pm to 4:30pm
8 Chains North Winery and Vineyards
Waterford, VA
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Live Music with Freddie Long

Saturday, Mar 29, 2025 from 2:00pm to 5:00pm
Purcellville, VA
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The Droptines and Max Alan

Saturday, Mar 29, 2025 at 7:00pm
The Monument
Winchester, VA
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The Droptines and Max Alan

Live Music with Ryan Benton

Sunday, Mar 30, 2025 from 2:00pm to 5:00pm
Purcellville, VA
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Brian Regan

Saturday, Apr 5, 2025 at 9:00pm
Hollywood Casino at Charles Town Races
Charles Town, WV
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Brian Regan

Live Dead & Brothers and Steve Kimock

Sunday, Apr 6, 2025 at 7:00pm
Bright Box Theater
Winchester, VA
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Live Dead & Brothers and Steve Kimock

Wednesday 13, Stitched Up Heart and more

Wednesday, Apr 9, 2025
Tally Ho Theatre
Leesburg, VA
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Wednesday 13, Stitched Up Heart and more

Bret Michaels: Birthday Celebration Show

Friday, Apr 11, 2025 at 8:00pm
Hollywood Casino at Charles Town Races
Charles Town, WV
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Bret Michaels: Birthday Celebration Show

Loco Wine Festival

Saturday, Apr 12, 2025 from 12:00pm to 5:00pm
Old Farm Winery at Hartland
Aldie, VA
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Loco Wine Festival

Rosie Soul

Saturday, Apr 12, 2025 at 8:00pm
Backseat Events
Winchester, VA
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Rosie Soul

Earthquake

Saturday, Apr 12, 2025 at 8:00pm
Hollywood Casino at Charles Town Races
Charles Town, WV
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Earthquake

Loco Wine Festival

Sunday, Apr 13, 2025 from 12:00pm to 5:00pm
Old Farm Winery at Hartland
Aldie, VA
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Loco Wine Festival
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