Upcoming Live Music Events

Nitty Gritty Dirt Band at The Monument

 The Monument 7 Jun 2026
MUSIC

Bryan Martin in Winchester

 Backseat Events 28 May 2026

Rodney Atkins in Winchester

 Backseat Events 24 Oct 2026
ENTERTAINMENT

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Upcoming Festivals Events

Hop Blossom Craft Beer Festival 2026

 Old Town Winchester 6 Jun 2026
BEER-FESTIVALS USD 9 TO 39

Strawberry Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 23 May 2026
FESTIVALS

Red, White, & Lights! Drone Show

 1001 E Cork St, Winchester, VA, United States, Virginia 22601 30 May 2026
FESTIVALS

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Upcoming Food & Drinks Events

Peach Festival

 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 8 Aug 2026
FESTIVALS

NAACP Winchester Area Juneteenth 2026

 Museum of the Shenandoah Valley 14 Jun 2026
JUNETEENTH

Sunflower Festival

2502 N. Frederick Pike, Winchester, VA 12 Sep 2026
FESTIVALS

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Upcoming Comedy Events

80s Prom Rescue Fundraiser

 Backseat Events 30 May 2026
DOG

"Hit Me 90's One More Time!" Comedy Murder Mystery Show (7PM)

 Bright Box Theater 6 Jun 2026
COMEDY

Winchester, VA @ Bright Box Theater

 Bright Box Theater 31 Jul 2026
PARTIES

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Upcoming Music Festivals Events

Strawberry Festival

 4305 Middle Road, Winchester, VA, United States, Virginia 22602 4305 Middle Rd, Winchester, VA 22602, United States 23 May 2026
FESTIVALS

Apple Harvest Festival

 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 10 Oct 2026
FESTIVALS

Honeycrisp Festival

 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 5 Sep 2026
FESTIVALS

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Trending Events in Winchester

Speed Dating & Ice Cream Social

 The Homestead Farm at Fruit Hill Orchard LLC 19 Jun 2026
SPEED-DATING USD 29

Independence at the Park - Red, White, and Boom!

 1001 E Cork St, Winchester, VA, United States, Virginia 22601 3 Jul 2026
KIDS

VA250 Fireworks Celebration

 4063 Middle Rd, Winchester, VA, United States, Virginia 22602 11 Jul 2026
FIREWORKS

KidzFest

 Old Town Winchester Walking Mall 13 Jun 2026
KIDS

Chris Cagle at Backseat Events

 Backseat Events 29 May 2026
CALENDAR

First Friday

 Old Town Winchester Walking Mall 7 Aug 2026
OPEN-MIC

Apple Harvest Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 3 Oct 2026
FESTIVALS

VIP Meet and Greet (General Admission Sold Separately)

 Backseat Events USA 4 Jun 2026
FITNESS USD 82

Winchester Police Dept. 5th Annual Auto Show

 100 W Piccadilly St, Winchester, VA 22601-3916, United States 23 May 2026
CAR-SHOWS

Samhain Luna Market 2026

 125 S. Loudoun Street, Winchester, VA 31 Oct 2026

Peaches & Beaches Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 1 Aug 2026
FESTIVALS

Homestead Harvest Festival

2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603 24 Oct 2026
FESTIVALS

Flutterby Fairy Festival 2026

 740 Merrimans Ln Winchester, VA 6 Jun 2026
FESTIVALS

39th Loudoun Street Mile

 1512 S Loudoun St, Winchester, VA 22601-4422, United States 25 May 2026
SPORTS

Kids Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 27 Jun 2026
FESTIVALS

More things to do in Winchester

Live Music
Festivals
Food & Drinks
Comedy
Fireworks
Music Festivals
St. Patrick's Day
Speed Dating
Pop-Ups