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Upperville Featured Events
Arts And Entertainment

Christmas in Middleburg - Tree Lighting Ceremony and Carols

Friday, Dec 5, 2025 at 5:00pm
Middleburg Museum
Middleburg, VA
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Christmas in Middleburg - Tree Lighting Ceremony and Carols

Cazhmiere

Friday, Dec 5, 2025 at 8:00pm
Backseat Events
Winchester, VA
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Cazhmiere

The Man In Black: Tribute To Johnny Cash

Friday, Dec 5, 2025 at 8:00pm
Hollywood Casino at Charles Town Races
Charles Town, WV
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The Man In Black: Tribute To Johnny Cash

The Local Honeys and Abby Hamilton

Friday, Dec 5, 2025 at 8:00pm
Bright Box Theater
Winchester, VA
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The Local Honeys and Abby Hamilton

Loudoun Jazz Ensemble Toy Drive Concert

Friday, Dec 5, 2025 at 8:00pm
Leesburg, VA
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Christmas in Middleburg

Saturday, Dec 6, 2025 at 8:00am
Middleburg, VA
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Christmas in Middleburg

Queensryche: Volume and Vengeance Tour

Saturday, Dec 6, 2025 at 8:00pm
Hollywood Casino at Charles Town Races
Charles Town, WV
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Queensryche: Volume and Vengeance Tour

Christmas in Middleburg - Christmas Pageant

Sunday, Dec 7, 2025 at 2:00pm
Foxcroft School
Middleburg, VA
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Christmas in Middleburg - Christmas Pageant

Keith Harkin

Tuesday, Dec 9, 2025 at 7:30pm
Bright Box Theater
Winchester, VA
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Keith Harkin

Bush

Friday, Dec 12, 2025 at 8:00pm
Hollywood Casino at Charles Town Races
Charles Town, WV
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Bush

Spencer Hatcher and Cedar Creek Grade

Friday, Dec 12, 2025 at 8:00pm
Backseat Events
Winchester, VA
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Spencer Hatcher and Cedar Creek Grade

Purcellville Holiday Parade

Saturday, Dec 13, 2025 at 12:00pm
Blue Ridge Middle School
Purcellville, VA
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Aaron Lewis and The Stateliners: American As It Gets Tour

Saturday, Dec 13, 2025 at 8:00pm
Hollywood Casino at Charles Town Races
Charles Town, WV
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Aaron Lewis and The Stateliners: American As It Gets Tour

Terry Oates & The Mudcats and Rusted Blue

Wednesday, Dec 31, 2025 at 8:00pm
Backseat Events
Winchester, VA
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Terry Oates & The Mudcats and Rusted Blue

That Arena Rock Show

Wednesday, Dec 31, 2025 at 10:30pm
Hollywood Casino at Charles Town Races
Charles Town, WV
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That Arena Rock Show
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