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Events and Things to do in Middletown, VA

Search for something you love or check out popular events in your area.

Charles Town Car Show 2026
Sat, Sep 5, 10:00 AM
Charles Town · 101 E Washington St
Charles Town Car Show 2026
Sat, Sep 5, 10:00 AM
Charles Town · 101 E Washington St
Watercolor Pet Portrait Class
Sat, Jul 18, 2:00 PM
Middleburg · Lost Barrel Brewing
Watercolor Pet Portrait Class
Sat, Jul 18, 2:00 PM
Middleburg · Lost Barrel Brewing
Proudly Poured: Pride in the Vines Kick Off Wine Festival
Sun, Jun 7, 2:00 PM
Middleburg · Mt. Defiance Cidery & Distillery
Proudly Poured: Pride in the Vines Kick Off Wine Festival
Sun, Jun 7, 2:00 PM
Middleburg · Mt. Defiance Cidery & Distillery
2026-50th Annual Mountain Heritage Arts & Crafts Festival
Fri, Sep 25, 10:00 AM
Kearneysville · Jefferson County WV Fairgrounds
2026-50th Annual Mountain Heritage Arts & Crafts Festival
Fri, Sep 25, 10:00 AM
Kearneysville · Jefferson County WV Fairgrounds
Miniature Book Nook Workshop
Sat, Sep 5, 11:00 AM
Charles Town · 119 E Washington St
Miniature Book Nook Workshop
Sat, Sep 5, 11:00 AM
Charles Town · 119 E Washington St
Middleburg Imagine Petite Retreat ✨ Reset, Refresh & Align
Sun, Jun 14, 9:00 AM
Middleburg · 22865 Foxcroft Rd
Middleburg Imagine Petite Retreat ✨ Reset, Refresh & Align
Sun, Jun 14, 9:00 AM
Middleburg · 22865 Foxcroft Rd
Annie Jr. Emerick Elementary Rising Stars
Fri, Jun 12, 6:30 PM
Purcellville · Franklin Park Performing & Visual Arts Center
Annie Jr. Emerick Elementary Rising Stars
Fri, Jun 12, 6:30 PM
Purcellville · Franklin Park Performing & Visual Arts Center
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
Spicy Saints Candle Workshop
Sat, Oct 3, 11:00 AM
Charles Town · 119 E Washington St
Spicy Saints Candle Workshop
Sat, Oct 3, 11:00 AM
Charles Town · 119 E Washington St
Storytelling Open Mic: Star-Spangled stories
Thu, May 28, 6:00 PM
Purcellville · Franklin Park Arts Center 540-338-7973
Storytelling Open Mic: Star-Spangled stories
Thu, May 28, 6:00 PM
Purcellville · Franklin Park Arts Center 540-338-7973
Almost full
Crew Campout - Luray, VA
Thu, Aug 6, 4:00 PM
Luray · Luray RV Resort on Shenandoah River
Almost full
Crew Campout - Luray, VA
Thu, Aug 6, 4:00 PM
Luray · Luray RV Resort on Shenandoah River
Bee Squash x Wakefield School
Fri, Jun 19, 9:30 AM + 7 more
The Plains · Wakefield School
Bee Squash x Wakefield School
Fri, Jun 19, 9:30 AM + 7 more
The Plains · Wakefield School
Proudly Poured: Pride in the Vines Kick Off Drag Brunch
Sun, Jun 7, 12:00 PM
Middleburg · Mt. Defiance Cidery & Distillery
Proudly Poured: Pride in the Vines Kick Off Drag Brunch
Sun, Jun 7, 12:00 PM
Middleburg · Mt. Defiance Cidery & Distillery
Annual Juneteenth Family Day Celebration: Hosted by The Barn at Evermore
Sat, Jun 20, 10:00 AM
Luray · 165 Kibler Dr
Annual Juneteenth Family Day Celebration: Hosted by The Barn at Evermore
Sat, Jun 20, 10:00 AM
Luray · 165 Kibler Dr
Artisan Pasta Making
Sun, May 31, 6:00 PM
Purcellville · Kalero Vineyard
Artisan Pasta Making
Sun, May 31, 6:00 PM
Purcellville · Kalero Vineyard
Sales end soon
2026 NoVA MusicFest benefiting Cancer Can Rock!
Sunday at 11:30 AM
Hillsboro · 868 Estate Vineyards
Sales end soon
2026 NoVA MusicFest benefiting Cancer Can Rock!
Sunday at 11:30 AM
Hillsboro · 868 Estate Vineyards
Paws and Paints @Devils Due
Sun, Jun 7, 1:00 PM
Kearneysville · Devil's Due Distillery
Paws and Paints @Devils Due
Sun, Jun 7, 1:00 PM
Kearneysville · Devil's Due Distillery
A Fest Less Ordinary
Sun, Jun 7, 12:00 PM
Hillsboro · 868 Estate Vineyards
A Fest Less Ordinary
Sun, Jun 7, 12:00 PM
Hillsboro · 868 Estate Vineyards
Sales end soon
Summer Awakening Sound Bath at Kalero Vineyards
Sunday at 8:00 PM
Purcellville · Kalero Vineyard
Sales end soon
Summer Awakening Sound Bath at Kalero Vineyards
Sunday at 8:00 PM
Purcellville · Kalero Vineyard
Sales end soon
ART OF TIE DYE & Next Wave Music Festival
Saturday at 10:00 AM
Hillsboro · Hillsboro Old Stone School
Sales end soon
ART OF TIE DYE & Next Wave Music Festival
Saturday at 10:00 AM
Hillsboro · Hillsboro Old Stone School

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:

Charles Town Car Show 2026

Watercolor Pet Portrait Class

Proudly Poured: Pride in the Vines Kick Off Wine Festival

2026-50th Annual Mountain Heritage Arts & Crafts Festival

Which events are currently trending in Middletown?

The trending searches this month in Middletown are:

cheddar rock 2026

vault and cellar

Which events are coming up?

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

ART OF TIE DYE & Next Wave Music Festival

2026 NoVA MusicFest benefiting Cancer Can Rock!

Summer Awakening Sound Bath at Kalero Vineyards

Storytelling Open Mic: Star-Spangled stories