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Events and Things to do in Middleburg, VA

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2026 Hunt Country Stable Tour
Upperville · Trinity Episcopal Church
2026 Hunt Country Stable Tour
Upperville · Trinity Episcopal Church
Going fast
8th Annual Plant-a-Thon, May 15th and 16th
Purcellville · JK Community Farm
Going fast
8th Annual Plant-a-Thon, May 15th and 16th
Purcellville · JK Community Farm
Star Wars at the Symphony
Sun, Jun 7, 3:00 PM
Ashburn · Stone Bridge High School
Star Wars at the Symphony
Sun, Jun 7, 3:00 PM
Ashburn · Stone Bridge High School
Sales end soon
Dueling Pianos Concert at Solace Brewing Company
Saturday at 7:00 PM
Sterling · Solace Brewing Company
Sales end soon
Dueling Pianos Concert at Solace Brewing Company
Saturday at 7:00 PM
Sterling · Solace Brewing Company
PFHCF and OCHCF 5k Run/Walk for Conservation
Mon, May 25, 8:00 AM
Middleburg · 23590 Stoke Farm Ln
PFHCF and OCHCF 5k Run/Walk for Conservation
Mon, May 25, 8:00 AM
Middleburg · 23590 Stoke Farm Ln
CEO Sisterhood Summer Social
Wed, Jun 3, 5:00 PM
Ashburn · The Barn at Brambleton
CEO Sisterhood Summer Social
Wed, Jun 3, 5:00 PM
Ashburn · The Barn at Brambleton
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
Scandinavian Spring Market at Walsh Family Wine
Sun, May 31, 10:00 AM
Purcellville · Walsh Family Wine
Scandinavian Spring Market at Walsh Family Wine
Sun, May 31, 10:00 AM
Purcellville · Walsh Family Wine
Going fast
Slow Flow Yoga with Rhonda
Saturday at 9:30 AM
Middleburg · Cana Vineyards and Winery of Middleburg
Going fast
Slow Flow Yoga with Rhonda
Saturday at 9:30 AM
Middleburg · Cana Vineyards and Winery of Middleburg
Almost full
The Afternoon Pour
Sunday at 2:30 PM
Round Hill · Williams Gap Tasting Room
Almost full
The Afternoon Pour
Sunday at 2:30 PM
Round Hill · Williams Gap Tasting Room
BuyOne BuildOne & Gratis 7 Films presents "Untethered" Documentary
Sat, Jun 13, 6:30 PM
Bluemont · Henway Hard Cider
BuyOne BuildOne & Gratis 7 Films presents "Untethered" Documentary
Sat, Jun 13, 6:30 PM
Bluemont · Henway Hard Cider
Sales end soon
Kim Hosen Memorial Hike - 2026
Saturday at 10:00 AM
Broad Run · 17502 Beverley Mill Dr
Sales end soon
Kim Hosen Memorial Hike - 2026
Saturday at 10:00 AM
Broad Run · 17502 Beverley Mill Dr
Ride for a Cause: YKM 2026 Cars & Motorcycles Car Show
Sat, May 30, 11:00 AM
Leesburg · 19201 Compass Creek Pkwy
Ride for a Cause: YKM 2026 Cars & Motorcycles Car Show
Sat, May 30, 11:00 AM
Leesburg · 19201 Compass Creek Pkwy
Going fast
HUNKS The Show at Craftwork Taproom (Gainesville, VA) 06/12/26
Fri, Jun 12, 9:00 PM
Gainesville · CraftWorx Taproom
Going fast
HUNKS The Show at Craftwork Taproom (Gainesville, VA) 06/12/26
Fri, Jun 12, 9:00 PM
Gainesville · CraftWorx Taproom
Leesburg Daybreak Rotary
Sat, Jun 6, 11:00 AM
Leesburg · 17558 Dry Mill Rd
Leesburg Daybreak Rotary
Sat, Jun 6, 11:00 AM
Leesburg · 17558 Dry Mill Rd
Big Band Jazz Night
Tuesday at 7:00 PM
Leesburg · Leesburg Junction
Big Band Jazz Night
Tuesday at 7:00 PM
Leesburg · Leesburg Junction
Sales end soon
Crusin' for a Cause
Saturday at 10:00 AM
Purcellville · 900 Degrees Brick Oven Pizza
Sales end soon
Crusin' for a Cause
Saturday at 10:00 AM
Purcellville · 900 Degrees Brick Oven Pizza
Going fast
STAR WARRIORS (Ages 4-7)
Tomorrow at 7:00 PM
Gainesville · 8050 Crescent Park Dr
Going fast
STAR WARRIORS (Ages 4-7)
Tomorrow at 7:00 PM
Gainesville · 8050 Crescent Park Dr
Introduction to Mushroom Growing at the JK Community Farm
Sun, May 24, 1:00 PM
Purcellville · JK Community Farm
Introduction to Mushroom Growing at the JK Community Farm
Sun, May 24, 1:00 PM
Purcellville · JK Community Farm
Going fast
Black Hoof Drag Bingo with Crimsyn
Tuesday at 7:00 PM
Leesburg · Black Hoof Brewing Company
Going fast
Black Hoof Drag Bingo with Crimsyn
Tuesday at 7:00 PM
Leesburg · Black Hoof Brewing Company

Trends in Middleburg

Explore more trends

Explore more trends

Frequently asked questions about Middleburg

What are the best events to attend?

According to Eventbrite, the best events are:

2026 Hunt Country Stable Tour

8th Annual Plant-a-Thon, May 15th and 16th

Star Wars at the Symphony

Dueling Pianos Concert at Solace Brewing Company

Which events are currently trending in Middleburg?

The trending searches this month in Middleburg are:

salamander resort the family reunion

mothers day brunch

salamander resort

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

STAR WARRIORS (Ages 4-7)

Slow Flow Yoga with Rhonda

Kim Hosen Memorial Hike - 2026

Crusin' for a Cause