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Events and Things to do in Middletown, VA

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Reitano's Jazz Night
Sat, Jun 13, 6:00 PM
Front Royal · Reitano Vineyards
Reitano's Jazz Night
Sat, Jun 13, 6:00 PM
Front Royal · Reitano Vineyards
DIY Microgreen Workshop with Robby Ds Lil Greens
Sun, Jun 14, 1:00 PM
Front Royal · Reitano Vineyards
DIY Microgreen Workshop with Robby Ds Lil Greens
Sun, Jun 14, 1:00 PM
Front Royal · Reitano Vineyards
Paws and Paints @Woodstock Brewhouse
Wed, Jun 10, 5:30 PM
Woodstock · Woodstock Brewhouse
Paws and Paints @Woodstock Brewhouse
Wed, Jun 10, 5:30 PM
Woodstock · Woodstock Brewhouse
Effective Change Management 1-Day Course in Winchester, VA
Friday at 9:00 AM + 7 more
Winchester · Regus Center
Effective Change Management 1-Day Course in Winchester, VA
Friday at 9:00 AM + 7 more
Winchester · Regus Center
Kisses For Charity!
Sat, May 30, 2:00 PM
Winchester · Peaceful Fields Sanctuary
Kisses For Charity!
Sat, May 30, 2:00 PM
Winchester · Peaceful Fields Sanctuary
24th Annual Tour de Skyline
Fri, Sep 11, 9:00 AM
Front Royal · Dickey Ridge Visitor Center
24th Annual Tour de Skyline
Fri, Sep 11, 9:00 AM
Front Royal · Dickey Ridge Visitor Center
Speed Dating & Ice Cream Social
Fri, Jun 19, 5:00 PM
Winchester · The Homestead Farm at Fruit Hill Orchard LLC
Speed Dating & Ice Cream Social
Fri, Jun 19, 5:00 PM
Winchester · The Homestead Farm at Fruit Hill Orchard LLC
CHEDDAR ROCK 2026
Fri, Jun 19, 12:00 PM
Middletown · Middletown
CHEDDAR ROCK 2026
Fri, Jun 19, 12:00 PM
Middletown · Middletown
Night Carbine
Sat, Jun 27, 5:30 PM
High View · 268 Caliber Dr
Night Carbine
Sat, Jun 27, 5:30 PM
High View · 268 Caliber Dr
Woes of Forgiveness - A Stage Play
Fri, Jun 19, 7:00 PM + 1 more
Front Royal · 155 Westminster Dr
Woes of Forgiveness - A Stage Play
Fri, Jun 19, 7:00 PM + 1 more
Front Royal · 155 Westminster Dr
Sales end soon
Experience fusion KARAOKE
Saturday at 5:00 PM + 31 more
Winchester · 1169 Berryville Ave
Sales end soon
Experience fusion KARAOKE
Saturday at 5:00 PM + 31 more
Winchester · 1169 Berryville Ave
Revolutionary War Guided Walking and Trolley Tour of Winchester, Virginia
Wed, Jul 1, 5:15 PM + 1 more
Winchester · 20 N Loudoun St
Revolutionary War Guided Walking and Trolley Tour of Winchester, Virginia
Wed, Jul 1, 5:15 PM + 1 more
Winchester · 20 N Loudoun St
VIP Meet and Greet (General Admission Sold Separately)
Thu, Jun 4, 8:00 PM
Winchester · Backseat Events USA
VIP Meet and Greet (General Admission Sold Separately)
Thu, Jun 4, 8:00 PM
Winchester · Backseat Events USA
The 22nd Annual Watermelon Pickers' Fest
Thu, Sep 10, 9:00 AM
Berryville · Clarke County Ruritan Fairgrounds
The 22nd Annual Watermelon Pickers' Fest
Thu, Sep 10, 9:00 AM
Berryville · Clarke County Ruritan Fairgrounds
Heaven's Pit presents Convictions with heal the hurt
Sun, Aug 2, 6:30 AM
Winchester · 1149 Valor Dr
Heaven's Pit presents Convictions with heal the hurt
Sun, Aug 2, 6:30 AM
Winchester · 1149 Valor Dr
2026 Hunt Country Stable Tour
Upperville · Trinity Episcopal Church
2026 Hunt Country Stable Tour
Upperville · Trinity Episcopal Church
Counter Contact Handgun
Sat, Aug 29, 8:30 AM
High View · 268 Caliber Dr
Counter Contact Handgun
Sat, Aug 29, 8:30 AM
High View · 268 Caliber Dr
Silvertung: The Red Tour! Feat. 12 Sins & Cursor
Fri, Jul 31, 7:00 PM
Winchester · Backseat Events USA
Silvertung: The Red Tour! Feat. 12 Sins & Cursor
Fri, Jul 31, 7:00 PM
Winchester · Backseat Events USA
Dine With Dead: Haunted Valarie Hill Vineyard
Sat, Oct 17, 6:00 PM
Stephens City · Valerie Hill Vineyard & Winery, Marlboro Road, Stephens City, VA, USA
Dine With Dead: Haunted Valarie Hill Vineyard
Sat, Oct 17, 6:00 PM
Stephens City · Valerie Hill Vineyard & Winery, Marlboro Road, Stephens City, VA, USA
Afternoon Retreat and Ceremonial Song Circle
Sat, May 30, 12:00 PM
Gore · The Land Celebration
Afternoon Retreat and Ceremonial Song Circle
Sat, May 30, 12:00 PM
Gore · The Land Celebration

Trends in Middletown

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Frequently asked questions about Middletown

What are the best events to attend?

According to Eventbrite, the best events are:

Reitano's Jazz Night

DIY Microgreen Workshop with Robby Ds Lil Greens

Paws and Paints @Woodstock Brewhouse

24th Annual Tour de Skyline

Which events are currently trending in Middletown?

The trending searches this month in Middletown are:

vault and cellar

cheddar rock 2026

Which events are coming up?

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

Effective Change Management 1-Day Course in Winchester, VA

Experience fusion KARAOKE

Afternoon Retreat and Ceremonial Song Circle

Kisses For Charity!